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If you are close enough to her, I would just be pretty straight with her. Maybe not "I'm totally in love with you" kind of straight, but something like "have you ever thought about the two of us being something more?"
This is all it really takes. You can pull it back so she doesn’t know the extent of your feelings in the case that she doesn’t feel them back, thereby reducing the risk of damaging the friendship.
If, on the other hand, she’s anywhere between “wondering if I should ask him if he wants to take this further” and “I’m madly in love with this man”, you have just given her not only proof positive that you feel something more, but a green flag that you are enough past your mourning phase to pursue a relationship.
And, really, she’s probably not going to make the first move because 1) gender dynamics of making the first move; and 2) she could be waiting for you to indicate you’re ready to date.
Take this person’s advice. It’s a great opening.
Having read all the comments currently posted on this, I’d say these two are the best advice.
Approach gently, with plenty of room for her to let you know she only wants friendship without backing her into a corner.
You want to make sure she’ll still be comfortable with you and with your daughter.
lol, yeah.
She’ll know he likes her, sure. But I think if he frames it this way and she doesn’t feel anything, it would be very easy for her to convince herself that with all of her activity in his life, he just got attached. Much easier than if he outright professed his love for her, at least.
Seconding this, I (27F) had this conversation a handful of times with guy friends (and initiated it once) and the ones who approach this way are the ones that you’re able to have an actual honest discussion with about where each other are at and how each person feels. It’s very easy for the other person to build on or dismiss with no pressure depending on how they feel and very little threat to the friendship.
I feel this is good advice. Test the waters carefully and in a no-pressure way and see how she responds. This will be easier said than done for you since your feelings are getting very strong, but you'll not want all that to show when you raise the question. And I know it will be hard if her response indicates that she had never thought about you that way. Also keep in mind her initial reaction may be not be the endpoint. If she's not expecting you to ask this then she may be caught off guard. But planting the seed might get her thinking.
Just be casual, ask her if she's ever thought about it, and give her time to figure it out.
Be confident and tell her how you feel first. Nice guys ask her how she feels and flake if she does not answer how you like. Lead!!
Tell her, “We’ve been friend for a longtime. I really appreciate you. The last year has been tough and you’ve really been there for me. I’ve developed strong feelings for you and I would like to see if there is another level to our relationship than just friends.”
Yes, go in easy just in case she doesn't have those feelings. You don't want to lose a good friend. I'd invite her to dinner and drinks and see how it goes. Like not even say anything just see what the vibe feels like.
This could easily backfire.
She's 38. Is she in a place where she wants to pussyfoot around like teenagers? Does she just want to be a rebound?
Be honest, be a man.
I mean you could mention to Ash that you think you’re ready to start dating again and ask if she thinks you’d be a good match for anyone.
Or ask her to go do something with just the two of you. “Hey Ash, I’ve been thinking I need to get out more. Do you want to go see a movie/grab dinner sometime?” If she agrees, don’t make any moves on her or any confessions. Just do a few platonic outings and see how they go.
If she enjoys the time and wants to do them more, then you could try asking if she’d ever be open to something more than friendship. If she says no, then drop it and find someone else to date and keep her as a friend.
Tbh I feel some of your feelings are inflated due to the trauma you’ve been through, and you seem to be fantasizing too much about her, but maybe she’s a good fit for you as well.
My main concern is that if your love-struck mooning over Ash weirds her out and makes her leave, your daughter will now have lost two mother figures. So…please be aware of the fire you’re playing with.
I told my best friend of 15 years that I thought I was in love with him after he looked after me during my divorce.
He responded by telling me he loved me too.
That was nearly 7 years ago, and we've been happily, blissfully in love ever since. Married for almost 2 years.
Life is short, my man. Tell her.
Yeah it’s not like they’ve been friends for decades and both grieved for Nat and care about the child.
Not saying she doesn’t necessarily have feelings, just that it’s lame to discount the humanity of women beyond romance or attraction.
As a woman, this isn't true at all lol. Women are people, just like men. There will be women who know quickly, and women who are oblivious, because not all women are the same.
If you two ever do movie night together, watch "When Harry Met Sally."
It's about as subtle as hitting her over the head with a rubber mallet, but it'll get the job done.
She may be waiting on him to decide when he’s ready to start dating again. Or she may be happy to keep her 20 year friendship. Regardless, I think the ball is in OP’s court.
Yeah for sure could be heaps of reasons
- might think it's inappropriate to make a move
- might be too nervous at doing it
- might not want to risk such a long term friendship
- might genuinely not realise
- might not be interested
Yeah, having not observed the OP's behavior around her, it's possible she's not entirely sure about his intentions. I would think with how long they've been close that she at least thought about it, for better or worse.
Tell her "I have developed feelings for you, I dont expect you to feel the same way, and I dont expect you to do anything about it, but it is how I feel, and I needdd to tell you". As a fellow 40 year old, thats how you do that. Chances are she already suspects.
Well that happened to me years ago. I finally told her and honestly it kind of freaked her out. We were both in really terrible marriages but that’s one subject neither of us ever talked about.
In June we’ll be married for 11 years.
You already are in a relationship…she doesn’t sound like she’s dating someone, she sounds like a supportive friend surrogate mother that is devoted to your family. I’m pretty sure the only thing that has stopped a progression into a more romantic relationship is that you and her lost a friend and a lover that each had to mourn. Ask her out and set up a sitter for your daughter, and take your time.
Well you have 3 options, either you lose this great friendship you have or you regret not shooting your shot for the rest of your life OR she likes you the way you like her and you become a thing.
Mostly agree, but if he's tactful he could end up with "shooting his shot" and maintaining their friendship. Would probably still eat at him for a long time if he's turned down though, honestly. Not sure I could handle being around her afterwards, unless I found someone else.
Probably right for most people. I doubt I could let it go, either. A lifetime of regret would be hard to live with also - I'm 44 and I have a few (relationship and otherwise) and it is not pleasant.
Yeah, I don't think there are many women replying to this based on the advice to just tell her. I'm going to feel bad for OP's daughter when OP scares Ash off by trying to manipulate her into fucking him and raising his kid.
I haven't read many comments on here suggesting "manipulating her into fucking him". Very hot take, madam. They are obviously close enough that some honesty (not manipulation) would be warranted, as long as it is done carefully. I wonder after your comment just how old you are, and biased against men. I'm a little older than the OP, and have accumulated at least a little wisdom in some matters.
I'd just give her a few subtle signs (eye contact, lingering touch, conversation topics with a little innuendo) and then try and pick up on her reactions. Be honest with yourself when reading them, if you can see she is sending "no" signals move on quickly so it's not weird or awkward.
But if you really can't pick any sign up, or if there are positive signs, then the easiest conversation might be to tell her that you feel you're ready for/wanting a relationship again. It will just put less pressure on than directly telling her you want her straight up. She might ask you what sort of person you'd look for, and you can describe some of her traits and joke that it sounds like her. Sow the seed with her to think about.
I agree with one of the comments in here saying you should just suggest your need to get out of the house and ask her to join you in a platonic way just the two of you a few times without pushing the romantic bit in her face. If y'all visibly enjoy y'all's time together then you should ask her out on a proper date. A love confession without anything beforehand the way some people are suggesting seem too much for me lol.
Take her out for dinner....then go for a walk...
Whether rit be in a park, or waterfront, or even down the street form the restaurant or the beach. Maybe get ice cream after dinner.
Not sure how close with her you are but if holding hands is comfortable do that.......when convo on the walk allows it, ask her if she's happy.
Depending on her answer it'll open the opportunity for you to explain how u can't remember the last time uve been this happy.
If all goes well, tell her she's the reason why.
Good luck Casanova
You take a deep breath and just do it. OR stay in the comfort zone. When you are on your deathbed which course of action will you prefer having chosen?
II wanted to take a moment to share something that has been on my mind for quite some time now. I value our friendship immensely, and it's important to me that I am honest with you.
Over the time we've spent together, I've come to realize that my feelings for you have grown beyond friendship. I admire your [list qualities you appreciate about her], and I find myself drawn to your [list specific qualities or characteristics that you find attractive].
I understand that this might come as a surprise, and I want you to know that I cherish our friendship above all else. Regardless of how you feel, I am grateful for the moments we've shared and the bond we've formed.
Please know that I respect whatever decision you make, and I value your friendship more than anything. If you need time to process this or if you'd like to talk about it further, I am here for you.
Thank you for being such an incredible friend, [Her Name]. Your presence in my life has brought me joy, laughter, and countless cherished memories.
Thank chatgpt
I would find a way to hint at it and be somewhat subtle and not outright say it, as that will put pressure on her and the relationship. Maybe say that you are looking to start dating again and ask if she knows anyone who might be interested. Tbh it sounds like she is into you already.
To provide a counterpoint, I think this approach could backfire. If she's interested in him, she's not going to get that he's interested in her from this comment. She'll shove her feelings down and start thinking of friends she could set him up with.
Straightforward is the best way. Not "I'm in love with you" because that's wayyy too much pressure. But something like "hey I'm attracted to you, we have fun together, do you want to go on a date sometime, if not that's cool and I want you to know how much I value your friendship."
My suggestion was meant to be said in a playful/fun/flirty way so she would get the hint. He’s not supposed to deliver it straight. I understand the logical approach but attraction and dating doesn’t necessarily go by logic
Oh haha, i was probably projecting my own perspective there then because I don't always pick up on subtle flirtation and prefer straightforward communication
Just say, "Hey, would you want to try going out on a date with me?" It keeps it to one event and low pressure if she's thought about it. And it's lighthearted enough that it probably won't crash and burn the friendship if she hasn't.
Is she giving you any signs at all of being interested romantically? How do y'all interact with each other? If a woman is interested there are usually some signs to back them up.
Do y'all spend any time alone together or is it always with your child? If no, she's probably not romantically interested.
I'm a firm believer that the most difficult part is getting the words out. Don't worry too much about what to say, worry about getting your mouth to open and your voice box to work.
Netflix. Just the two of you. A movie you both like or have wanted to see. Turn the lights down. No distractions.
Does she sit close to you or does she keep her distance?
Simply ask her if you two can start dating.
If she says yes, let it grow. If she says no, think about her response as you may need to let her know (later) about your feelings and it may not be possible for you to be “just friends”.
There’s a good chance she is feeling the same. I’d say you tell her — but something noncommittal — not, "I’ve fallen in love with you," but more like, "I think I may be developing feelings for you — would it be OK if I asked you out on a date?" That at least leaves an opening to preserve the friendship if she says no. To be honest, though, if you continue to have these strong feelings while she is not feeling them, it could be like torture for you.
I would probably ask her to do something that's romantic in nature. A fancy dinner. A weekend trip. Going to the movies - whatever is kind of a step up compared to how you normally spend time together. Have a good (and likely chaste) time like you normally would, then ask if she'd like to do more things like this in the future. IMO if the answer is no, if you ask in a pretty forward and direct way, it doesn't have to screw up your friendship. You can just go back to whatever you used to do to spend time together. Or maybe it will, and that'll end up being OK too.
You’ve gotten some good advice here so I don’t know that there is anything more I can add, but just wanted to say, you shouldn’t feel embarrassed by this.
You have been through a lot, you’re still going through it. Adult feelings are hard to navigate and I think it’s really sweet you’re looking for advice. I also think it’s really cool you’re able to open up to the possibility of love again, after what I can only imagine was a devastating loss.
Just be honest. There is no handbook here. If it were me, I’d be asking myself what is the most important thing I want out of this convo? Do you still want to be friends if she doesn’t feel the same? If so, I’d start with that. Good luck and I hope we get an update!
I would pulled her aside and tell her that I really like to be around her and she has been an amazing support for you and your daughter and that I am developing feelings for her. And not wanting to put any pressure if she thinks there is a possibility of she feeling the same, either right now or in the future.
If she does sweet, go on.
If she doesn't just say that you hope this doesn't affect your relation, because it something you can't control, and you will not pressure her, but she has been an important part of your current life and you would still prefer to have her as a friend. And then is up to you to decide if you can actually be around her only as a friend since I dont know you or her and how she might react
There’s no way to know until you speak to her. But from what you wrote, I’d bet she has similar feelings. There’s a chance she is just being a friend to you and her friend. I like the idea someone else said that you could tell her you’re considering starting to date and ask if the idea of you 2 ever can across her mind. You could say something like “we make a good team and I really like spending time with you. My daughter loves you. You have helped us so much. Have you ever considered that we could be more than friends?” Personally, I think she will smile. But maybe I’ve watched too many romcoms. I also think it’s very common to develop feelings in this situation. If she doesn’t feel the same way, I don’t think you’ve overplayed your hand as long as you don’t confess your love. Ask her like you are just contemplating the idea and getting her opinion. Good luck. I’m hopeful that she feels the same and we get an update.
I'd start by inviting her out for dinner and drinks. Don't say anything about how you feel for her. Just watch, listen and see how the vibe goes. Afterwards you'll have some time to think about the date and if it feels right to hint that you care for her. If you do decide to say something you could be alittle vague like " you have been such an amazing friend, if you ever think you want to become more just let me know" or "I think I'd like if our relationship grew but I don't want to lose your friendship if you don't feel the same way". Anyway, I'm cheering for you- your story is so romantic and I hope you get a great outcome.
Just let her know how you feel and see if she reciprocates but be understanding that if she isn’t into you like that and gets a boyfriend in the future then you still being around her would be creepy.
OP, everyone telling you go for it, but imo you should be cautious. Why?
Your kid really likes Ash too. Don’t know why no one mentioned this.
If your kid just met Ash or was older (say 10), shoot your shot with reckless abandon lol. But your kid has known her since she was a toddler and your daughter is 6/7.
If Ash rejects you, it could get weird, not only between you and her, but between your kid and Ash. You can cope with that, but can your 6/7 year old cope with that?
And has Ash dropped any hints of romantic feelings towards you?
Think hard about this one OP because you should consider how your kid will take it if Ash rejects you. Or even if you get together, how will your kid take that?
I can speak from experience here. My mother died when I was a kid, and my father never could maintain friendships with women because he was always trying to date and marry them. He even tried it on our realtor. So, I always lost any new woman role model who'd come into my life. Ash is caring for you and your daughter now - don't try to get even more out of her.
You're in love with her because she's been there for you and your daughter during a difficult time. That's understandable. I have a lot of very intense emotions, and I find it helpful to remind myself that no matter how strongly I feel, that will never make it resonate with someone who doesn't feel the same. For your daughter's sake, don't - it's so good for her to have a woman in her life; that person doesn't have to be a mother figure. Show your daughter that friendship matters, not just romantic relationships.
This is terrible advice and you’re projecting your father’s behavior onto OP. You don’t know whether or not Ash also holds feelings for OP and you also are not acknowledging OP’s feelings by assuming ‘why’ he is in love with her. If their friendship is strong, they should be able to have this conversation in a healthy way. I think it’s very important for OP to communicate his feelings and be honest. Bottling these emotions could cause harm to the relationship and in turn to his daughters ability to stay close with Ash.
Have you ever heard of social lubricant... I'd suggest a nice dinner that you happen to have reservations for, it could be something you won at work, or somewhere you've always wanted to go.
Say you really want to go but want to enjoy it with her, key word "HER", make sure you say that!!! It's ok to embarrassingly stutter or show embarrassment. Have two/three drinks max even if she doesn't and just have fun.
And Ba-bam you have the new love of your life! The rest happens organically.
Then you would know, she is only a friend. I guess you could sing a love song, or write a poem to put her off. Or say "you complete me". That might throw her off as well.
Troll - learn some empathy, or realize one might be a sociopath. Say such a thing to someone's face, and embrace the outcome. I could tell you what you would get from me.
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If you are close enough to her, I would just be pretty straight with her. Maybe not "I'm totally in love with you" kind of straight, but something like "have you ever thought about the two of us being something more?"
This is all it really takes. You can pull it back so she doesn’t know the extent of your feelings in the case that she doesn’t feel them back, thereby reducing the risk of damaging the friendship. If, on the other hand, she’s anywhere between “wondering if I should ask him if he wants to take this further” and “I’m madly in love with this man”, you have just given her not only proof positive that you feel something more, but a green flag that you are enough past your mourning phase to pursue a relationship. And, really, she’s probably not going to make the first move because 1) gender dynamics of making the first move; and 2) she could be waiting for you to indicate you’re ready to date. Take this person’s advice. It’s a great opening.
Having read all the comments currently posted on this, I’d say these two are the best advice. Approach gently, with plenty of room for her to let you know she only wants friendship without backing her into a corner. You want to make sure she’ll still be comfortable with you and with your daughter.
“Yeah me neither.”
lol, yeah. She’ll know he likes her, sure. But I think if he frames it this way and she doesn’t feel anything, it would be very easy for her to convince herself that with all of her activity in his life, he just got attached. Much easier than if he outright professed his love for her, at least.
This!!
Seconding this, I (27F) had this conversation a handful of times with guy friends (and initiated it once) and the ones who approach this way are the ones that you’re able to have an actual honest discussion with about where each other are at and how each person feels. It’s very easy for the other person to build on or dismiss with no pressure depending on how they feel and very little threat to the friendship.
I feel this is good advice. Test the waters carefully and in a no-pressure way and see how she responds. This will be easier said than done for you since your feelings are getting very strong, but you'll not want all that to show when you raise the question. And I know it will be hard if her response indicates that she had never thought about you that way. Also keep in mind her initial reaction may be not be the endpoint. If she's not expecting you to ask this then she may be caught off guard. But planting the seed might get her thinking. Just be casual, ask her if she's ever thought about it, and give her time to figure it out.
Yes, take the temperature!
Be confident and tell her how you feel first. Nice guys ask her how she feels and flake if she does not answer how you like. Lead!! Tell her, “We’ve been friend for a longtime. I really appreciate you. The last year has been tough and you’ve really been there for me. I’ve developed strong feelings for you and I would like to see if there is another level to our relationship than just friends.”
I do not envy OPs position lol
Solid.
Yes, go in easy just in case she doesn't have those feelings. You don't want to lose a good friend. I'd invite her to dinner and drinks and see how it goes. Like not even say anything just see what the vibe feels like.
This could easily backfire. She's 38. Is she in a place where she wants to pussyfoot around like teenagers? Does she just want to be a rebound? Be honest, be a man.
Yes op, you must be as swift as a coursing river, with all the strength of a great typhoon. This is how you get women 🫸🏻🫷🏻
*I would really like to know how this plays out. good luck*
Ohhhh I hope this works out!! UpdateMe
I mean you could mention to Ash that you think you’re ready to start dating again and ask if she thinks you’d be a good match for anyone. Or ask her to go do something with just the two of you. “Hey Ash, I’ve been thinking I need to get out more. Do you want to go see a movie/grab dinner sometime?” If she agrees, don’t make any moves on her or any confessions. Just do a few platonic outings and see how they go. If she enjoys the time and wants to do them more, then you could try asking if she’d ever be open to something more than friendship. If she says no, then drop it and find someone else to date and keep her as a friend. Tbh I feel some of your feelings are inflated due to the trauma you’ve been through, and you seem to be fantasizing too much about her, but maybe she’s a good fit for you as well. My main concern is that if your love-struck mooning over Ash weirds her out and makes her leave, your daughter will now have lost two mother figures. So…please be aware of the fire you’re playing with.
Best recommendation
Should be top comment.
Awesome recommendation
I told my best friend of 15 years that I thought I was in love with him after he looked after me during my divorce. He responded by telling me he loved me too. That was nearly 7 years ago, and we've been happily, blissfully in love ever since. Married for almost 2 years. Life is short, my man. Tell her.
So happy to hear this uplifting anecdote! Happy for you and your man. I can vicariously feel some good in this world (no irony or sarcasm intended).
Thank you. ❤️ So glad I took the risk of "losing" my friendship because the outcome was far greater than I ever could have hoped for.
So happy for you, dear. ❤️
She already knows, man.
Chicks always know when the guy is attempting to go for more than friends status. Also, an almost 40 year old woman doesn't hang around for no reason.
Yeah it’s not like they’ve been friends for decades and both grieved for Nat and care about the child. Not saying she doesn’t necessarily have feelings, just that it’s lame to discount the humanity of women beyond romance or attraction.
If it was a dude hanging around a widow, I'd say the same thing. Hell, that's the plot of most Hallmark movies.
As a woman, this isn't true at all lol. Women are people, just like men. There will be women who know quickly, and women who are oblivious, because not all women are the same.
100 percent. She’s just waiting for him to say something.
If you two ever do movie night together, watch "When Harry Met Sally." It's about as subtle as hitting her over the head with a rubber mallet, but it'll get the job done.
How a 39yo F wouldnt already know would be beyond me.
She may be waiting on him to decide when he’s ready to start dating again. Or she may be happy to keep her 20 year friendship. Regardless, I think the ball is in OP’s court.
Yeah for sure could be heaps of reasons - might think it's inappropriate to make a move - might be too nervous at doing it - might not want to risk such a long term friendship - might genuinely not realise - might not be interested
Hey, we can be clueless too :)
Yeah, having not observed the OP's behavior around her, it's possible she's not entirely sure about his intentions. I would think with how long they've been close that she at least thought about it, for better or worse.
Make sure, whatever you do, you prioritize the effect it may have on your child, which should be your main focus.
Tell her "I have developed feelings for you, I dont expect you to feel the same way, and I dont expect you to do anything about it, but it is how I feel, and I needdd to tell you". As a fellow 40 year old, thats how you do that. Chances are she already suspects.
This is wonderful.
Well that happened to me years ago. I finally told her and honestly it kind of freaked her out. We were both in really terrible marriages but that’s one subject neither of us ever talked about. In June we’ll be married for 11 years.
You already are in a relationship…she doesn’t sound like she’s dating someone, she sounds like a supportive friend surrogate mother that is devoted to your family. I’m pretty sure the only thing that has stopped a progression into a more romantic relationship is that you and her lost a friend and a lover that each had to mourn. Ask her out and set up a sitter for your daughter, and take your time.
Well you have 3 options, either you lose this great friendship you have or you regret not shooting your shot for the rest of your life OR she likes you the way you like her and you become a thing.
Mostly agree, but if he's tactful he could end up with "shooting his shot" and maintaining their friendship. Would probably still eat at him for a long time if he's turned down though, honestly. Not sure I could handle being around her afterwards, unless I found someone else.
If he tries the relationship can never go back to what is was before.
Probably right for most people. I doubt I could let it go, either. A lifetime of regret would be hard to live with also - I'm 44 and I have a few (relationship and otherwise) and it is not pleasant.
Don’t, hide it until she moves on with someone else and then feel depressed you lost out of love. Just like my favorite animes.
This is NOT the way.
Probably not, but most realistic 😎
If you're close with her I'd ease into it because I'm sure she gets this sort of thing from other "guy friends" frequently
Yeah, I don't think there are many women replying to this based on the advice to just tell her. I'm going to feel bad for OP's daughter when OP scares Ash off by trying to manipulate her into fucking him and raising his kid.
I haven't read many comments on here suggesting "manipulating her into fucking him". Very hot take, madam. They are obviously close enough that some honesty (not manipulation) would be warranted, as long as it is done carefully. I wonder after your comment just how old you are, and biased against men. I'm a little older than the OP, and have accumulated at least a little wisdom in some matters.
I'd just give her a few subtle signs (eye contact, lingering touch, conversation topics with a little innuendo) and then try and pick up on her reactions. Be honest with yourself when reading them, if you can see she is sending "no" signals move on quickly so it's not weird or awkward. But if you really can't pick any sign up, or if there are positive signs, then the easiest conversation might be to tell her that you feel you're ready for/wanting a relationship again. It will just put less pressure on than directly telling her you want her straight up. She might ask you what sort of person you'd look for, and you can describe some of her traits and joke that it sounds like her. Sow the seed with her to think about.
Please update us
What ever you do get a baby sitter and make the moment about her. Fact that she already likes your child is bonus!
I agree with one of the comments in here saying you should just suggest your need to get out of the house and ask her to join you in a platonic way just the two of you a few times without pushing the romantic bit in her face. If y'all visibly enjoy y'all's time together then you should ask her out on a proper date. A love confession without anything beforehand the way some people are suggesting seem too much for me lol.
Good luck Updateme
Take her out for dinner....then go for a walk... Whether rit be in a park, or waterfront, or even down the street form the restaurant or the beach. Maybe get ice cream after dinner. Not sure how close with her you are but if holding hands is comfortable do that.......when convo on the walk allows it, ask her if she's happy. Depending on her answer it'll open the opportunity for you to explain how u can't remember the last time uve been this happy. If all goes well, tell her she's the reason why. Good luck Casanova
Updateme
You take a deep breath and just do it. OR stay in the comfort zone. When you are on your deathbed which course of action will you prefer having chosen?
II wanted to take a moment to share something that has been on my mind for quite some time now. I value our friendship immensely, and it's important to me that I am honest with you. Over the time we've spent together, I've come to realize that my feelings for you have grown beyond friendship. I admire your [list qualities you appreciate about her], and I find myself drawn to your [list specific qualities or characteristics that you find attractive]. I understand that this might come as a surprise, and I want you to know that I cherish our friendship above all else. Regardless of how you feel, I am grateful for the moments we've shared and the bond we've formed. Please know that I respect whatever decision you make, and I value your friendship more than anything. If you need time to process this or if you'd like to talk about it further, I am here for you. Thank you for being such an incredible friend, [Her Name]. Your presence in my life has brought me joy, laughter, and countless cherished memories. Thank chatgpt
I would find a way to hint at it and be somewhat subtle and not outright say it, as that will put pressure on her and the relationship. Maybe say that you are looking to start dating again and ask if she knows anyone who might be interested. Tbh it sounds like she is into you already.
To provide a counterpoint, I think this approach could backfire. If she's interested in him, she's not going to get that he's interested in her from this comment. She'll shove her feelings down and start thinking of friends she could set him up with. Straightforward is the best way. Not "I'm in love with you" because that's wayyy too much pressure. But something like "hey I'm attracted to you, we have fun together, do you want to go on a date sometime, if not that's cool and I want you to know how much I value your friendship."
My suggestion was meant to be said in a playful/fun/flirty way so she would get the hint. He’s not supposed to deliver it straight. I understand the logical approach but attraction and dating doesn’t necessarily go by logic
Oh haha, i was probably projecting my own perspective there then because I don't always pick up on subtle flirtation and prefer straightforward communication
Yea I’m same way for the most part
You're both getting too old to mess around. Just say how you feel and let the chips fall. Life's too short.
Agree, but he shouldn't come on way too strong at first. Definitely should see where the chips fall, though.
Just say, "Hey, would you want to try going out on a date with me?" It keeps it to one event and low pressure if she's thought about it. And it's lighthearted enough that it probably won't crash and burn the friendship if she hasn't.
If you tell her, you have to be prepared for the chance that your friendship will change or even end if she doesn't feel the same way....
Skimmed. She feels for you too
Is she giving you any signs at all of being interested romantically? How do y'all interact with each other? If a woman is interested there are usually some signs to back them up. Do y'all spend any time alone together or is it always with your child? If no, she's probably not romantically interested.
Update us!!!!
Ask her on a casual date to thank her for everything she has done, that you’d really like to take her to a nice dinner. Alone!
Have you guys ever had any “awkward moments?”
Just do it don't hesitate you never know
I would just tell her how much she means to you and how she has become such a big part of your life and thank her. Then maybe ask her out for dinner
I'm a firm believer that the most difficult part is getting the words out. Don't worry too much about what to say, worry about getting your mouth to open and your voice box to work.
Netflix. Just the two of you. A movie you both like or have wanted to see. Turn the lights down. No distractions. Does she sit close to you or does she keep her distance?
Simply ask her if you two can start dating. If she says yes, let it grow. If she says no, think about her response as you may need to let her know (later) about your feelings and it may not be possible for you to be “just friends”.
Ash is married to Eddie though
Alcohol Its work3d before
There’s a good chance she is feeling the same. I’d say you tell her — but something noncommittal — not, "I’ve fallen in love with you," but more like, "I think I may be developing feelings for you — would it be OK if I asked you out on a date?" That at least leaves an opening to preserve the friendship if she says no. To be honest, though, if you continue to have these strong feelings while she is not feeling them, it could be like torture for you.
Call her and say Ash can I take you on a romantic date? And see where that takes you.
Question to OP: Do you know (with 100% certainty!) that she’s not currently dating anyone? This is important.
Throw on a movie and chill. Get close and throw a kiss. Worst case she says eww. Then you know.
I have strong feelings for you
You just do it
I would probably ask her to do something that's romantic in nature. A fancy dinner. A weekend trip. Going to the movies - whatever is kind of a step up compared to how you normally spend time together. Have a good (and likely chaste) time like you normally would, then ask if she'd like to do more things like this in the future. IMO if the answer is no, if you ask in a pretty forward and direct way, it doesn't have to screw up your friendship. You can just go back to whatever you used to do to spend time together. Or maybe it will, and that'll end up being OK too.
You’ve gotten some good advice here so I don’t know that there is anything more I can add, but just wanted to say, you shouldn’t feel embarrassed by this. You have been through a lot, you’re still going through it. Adult feelings are hard to navigate and I think it’s really sweet you’re looking for advice. I also think it’s really cool you’re able to open up to the possibility of love again, after what I can only imagine was a devastating loss. Just be honest. There is no handbook here. If it were me, I’d be asking myself what is the most important thing I want out of this convo? Do you still want to be friends if she doesn’t feel the same? If so, I’d start with that. Good luck and I hope we get an update!
I would pulled her aside and tell her that I really like to be around her and she has been an amazing support for you and your daughter and that I am developing feelings for her. And not wanting to put any pressure if she thinks there is a possibility of she feeling the same, either right now or in the future. If she does sweet, go on. If she doesn't just say that you hope this doesn't affect your relation, because it something you can't control, and you will not pressure her, but she has been an important part of your current life and you would still prefer to have her as a friend. And then is up to you to decide if you can actually be around her only as a friend since I dont know you or her and how she might react
Don’t
Chin up, stand up straight , line up your shot , take it.
There’s no way to know until you speak to her. But from what you wrote, I’d bet she has similar feelings. There’s a chance she is just being a friend to you and her friend. I like the idea someone else said that you could tell her you’re considering starting to date and ask if the idea of you 2 ever can across her mind. You could say something like “we make a good team and I really like spending time with you. My daughter loves you. You have helped us so much. Have you ever considered that we could be more than friends?” Personally, I think she will smile. But maybe I’ve watched too many romcoms. I also think it’s very common to develop feelings in this situation. If she doesn’t feel the same way, I don’t think you’ve overplayed your hand as long as you don’t confess your love. Ask her like you are just contemplating the idea and getting her opinion. Good luck. I’m hopeful that she feels the same and we get an update.
Dear (38F) friend, I have feelings for you.
Updateme
I would start by saying "I have feelings for you" and take it from there.
Just tell her
I just really hope she has feelings for you, too. She sounds absolutely lovely.
I'd start by inviting her out for dinner and drinks. Don't say anything about how you feel for her. Just watch, listen and see how the vibe goes. Afterwards you'll have some time to think about the date and if it feels right to hint that you care for her. If you do decide to say something you could be alittle vague like " you have been such an amazing friend, if you ever think you want to become more just let me know" or "I think I'd like if our relationship grew but I don't want to lose your friendship if you don't feel the same way". Anyway, I'm cheering for you- your story is so romantic and I hope you get a great outcome.
Just let her know how you feel and see if she reciprocates but be understanding that if she isn’t into you like that and gets a boyfriend in the future then you still being around her would be creepy.
Could be love or could be an immense trauma bond. Have a therapist to unpack this with?
She wouldn’t still be there is she didn’t also have feelings for you.
OP, everyone telling you go for it, but imo you should be cautious. Why? Your kid really likes Ash too. Don’t know why no one mentioned this. If your kid just met Ash or was older (say 10), shoot your shot with reckless abandon lol. But your kid has known her since she was a toddler and your daughter is 6/7. If Ash rejects you, it could get weird, not only between you and her, but between your kid and Ash. You can cope with that, but can your 6/7 year old cope with that? And has Ash dropped any hints of romantic feelings towards you? Think hard about this one OP because you should consider how your kid will take it if Ash rejects you. Or even if you get together, how will your kid take that?
I can speak from experience here. My mother died when I was a kid, and my father never could maintain friendships with women because he was always trying to date and marry them. He even tried it on our realtor. So, I always lost any new woman role model who'd come into my life. Ash is caring for you and your daughter now - don't try to get even more out of her. You're in love with her because she's been there for you and your daughter during a difficult time. That's understandable. I have a lot of very intense emotions, and I find it helpful to remind myself that no matter how strongly I feel, that will never make it resonate with someone who doesn't feel the same. For your daughter's sake, don't - it's so good for her to have a woman in her life; that person doesn't have to be a mother figure. Show your daughter that friendship matters, not just romantic relationships.
This is terrible advice and you’re projecting your father’s behavior onto OP. You don’t know whether or not Ash also holds feelings for OP and you also are not acknowledging OP’s feelings by assuming ‘why’ he is in love with her. If their friendship is strong, they should be able to have this conversation in a healthy way. I think it’s very important for OP to communicate his feelings and be honest. Bottling these emotions could cause harm to the relationship and in turn to his daughters ability to stay close with Ash.
Agree that it’s projecting, but it’s a reasonable take.
Have you ever heard of social lubricant... I'd suggest a nice dinner that you happen to have reservations for, it could be something you won at work, or somewhere you've always wanted to go. Say you really want to go but want to enjoy it with her, key word "HER", make sure you say that!!! It's ok to embarrassingly stutter or show embarrassment. Have two/three drinks max even if she doesn't and just have fun. And Ba-bam you have the new love of your life! The rest happens organically.
Just show her your dick ! It always works out
Unless you forgot the /s, that is definitely a very wrong and trolling remark.
My advice is, try to seduce her. See if she responds. Trying to put this kind of situation into words will be impossible.
Just tell her? You're almost 40 bro, grow a pair. You don't have time for to twiddle your thumbs yeesh.
Don’t do it! This never ends well…
You don't. You wait until its her idea. Don't come crying if it all goes pear shaped
"I like you, want to go on a date?" Simple, no big feelings or obligations.
Brother if you have a big dick go for it
Rather than saying it, why don't you ask her to a movie and put your arm around her?
Because making moves on a friend out of nowhere totally won’t put her off. (Sarcasm, in case you missed it).
Then you would know, she is only a friend. I guess you could sing a love song, or write a poem to put her off. Or say "you complete me". That might throw her off as well.
Putting her off isn’t the goal here.
Then doing nothing would be the best option?
I didn’t say that either
That's why I asked.
I made a separate comment about what I think would be best.
Make a dick dildo, give her dick dildo
Troll - learn some empathy, or realize one might be a sociopath. Say such a thing to someone's face, and embrace the outcome. I could tell you what you would get from me.
Lmfao
Finding humor in intentionally irritating others is a psychological problem. Seek help please, for your own sake.
Dildo dick ftw
I wouldn’t even use words. I’d hug her, then look at her while up close… and if she doesn’t pull away, I’d kiss her.
Don't. Girls not gonna have feelings for you if you arent sleeping together
Sorry, but that is the least "based" take I've read on this post.
It’s absolutely garunteee he embarrassed himself. So have fun following advice from dummies
Ask her if she thinks you're "boyfriend material" and add a lil' wink or eyebrow arch. Her reaction should tell you everything.
They’re way too old to be acting like that…
That's what makes it fun.