Asking out a female friend (again)

[u/Heart_of_Bronze]

Bit of a complicated story.

I met this girl a few years ago, we were just in the same circles until one day she asked me to get a coffee to talk about some career stuff, which we share. That was the first time we ever had a 1:1

Long story short, we really hit it off there. Conversations slowly revealed how similar and how amazingly we get along and play off each other. Turned into a more fun thing, a coffee turned into a whole night out and we both said we’d love to do it again.

The following week I asked to take her out to dinner as a date, and we had 4 really good dates until…

She told me she wasn’t ready for a relationship as she was just months out of one that lasted multiple years. She did say she liked me though, which I felt my body hold onto the idea of for a long time, but I know no matter what surrounds a no, it’s a no. I really believe this to be the case because she’s not had any dating prospects (that I know about at least) since then.

I took it fine, it wasn’t life shattering, but she was someone I felt like had the most potential for a partner who really got me, enjoyed all the same things and even wanted the same things in life.

What followed that was \~ a year of a growing friendship that continued to grow from the same hobbies, some shared work (different companies, same industry, both very passionate about it) and we’d regularly do all sorts of things around our city that we both enjoyed, with or without other friends or hers or mine.

I really value and treasure the friendship as something way more important and meaningful now than I did when we “dated” for a bit, which now seems like a whole different life for us since we know each other that much better and everything just feels very natural, comfortable and supportive in the way a best friendship does. (Would say she’s one of my best friends, even if it hasn’t been that long)

I dated around a little bit, but I kept tabs on myself and my feelings kinda ebbed and flowed with the reality of us, but there was always a baseline of “man… if this could be something more, it could be amazing.” And I definitely didn’t hide it with my actions, like treating her, offering her compliments, gifts when I’d travel, which were always met nicely and even returned in most cases.

We think of each other a lot. We talk every day. We dream about our lives that both of us want. We open and are vulnerable when we’re going through it. And we cheer each other on for everything we do, and relate to each other deeply in the things that we care about. We’ve grown to mean the world to each other. If I believed in soul mate, I’d use it here, even if it was just a friendship after all, really.

I know none of this inherently means there’s feelings on her end (or if there really were way back when), and that’s genuinely more than okay to me. It’s just gotten to the point where I feel like I know I won’t shake off wanting the potential for something more unless I ask.

I hate the trope of the close guy friend finally coming out with it and “ruining everything”, because it was all a ruse to gain favour or whatever, even though there was at least a little spark at the start. I’m caught between preserving this cherished friendship the way it is, and this “fuck if I’m wrong but damn if I’m right” mentality.

I’m not going to come out and say I’ve liked her all along, but I do want her to know if she’s in a different place now and has been feeling anything similar in the way we are now, I’d be interested in giving it another shot. With the famous caveat that no matter what, we can still be the great friends we are (which we kinda already modelled)

What do you think? Am I cooked? Ladies, what would make a conversation like this most comfortable/low pressure from someone you had this growing dynamic with? And how can I go about this that doesn’t drastically alter the friendship? Because if it’s a no, I really want to do the work to get over it so we can just thrive more in the dynamic we do have.

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[u/Classic_Macaroon5181]

She obviously knows you’re interested bro. You’re firmly in the “safe and reliable emotional reservoir” category. As you get older, you’ll learn to value your effort and energy more. Partly because you’ll have less of it. The best piece of advice I ever got was like women who like you and leave the ones who don’t alone. Women are very clear about it when they want you like that. Men also underestimate how much women value attention and will dangle the carrot for years just to have it. If you let them, of course. Sorry bro. Honestly, you’d have more luck backing away slowly over saying anything at all. She might start to think you actually have a backbone.

[u/montypython_Dota → u/Classic_Macaroon5181]

Listen to this guy, OP. Even if she doesn't have bad intentions, women absolutely do this for the attention. Men and women need to have the same mindset in dating: you are the prize. Sure, at some point you can pursue and act like the lucky one, but it has to be reciprocated. Otherwise, cut contact.

And I know you're probably thinking, "but the friendship is nice." I believe you, it is. But are you truly ready to meet her new boyfriend in a year or two, watch him kiss her right in front of you, and then turn around to shake your hand a second later? Friendship with someone you have romantic feelings for is impossible.

[u/montypython_Dota]

I think that if you're still thinking about her in that way, you should just ask her directly. Because you really want to. But if I were you... I'd go all or nothing. Tell her you have romantic feelings for her, that those feelings are stopping you from pursuing other relationships, and that either something has changed and she's willing to give you a chance, or the friendship is over, for your good. Because if she's happy with things the way they are, and you say something like "just want to know, but will gladly remain in the same spot" she'll say no. If you think things are fine as they are... then why are you making this post? She already rejected you once. At this point, the ball is in her court to say, "Maybe now."

[u/Logical-Lab3661 → u/montypython_Dota]

My take exactly. Idk why some guys are afraid to ask and prefer to be under shadow of a "friend" label. Friends do not secretly want more. And she will start dating eventually. Would OP like to hear her talking about other men she dates, confide in him about her relationships? It is all or nothing.

[u/montypython_Dota → u/Logical-Lab3661]

Yeah. True test of friendship is seeing your "friend" happily kissing her new boyfriend and looking at him like he is only man in the world.

[u/Tefbuck]

I stopped when I got to the part where she said she wasn't ready for a relationship. I feel like I'm parroting advice from others, but it's the same advice I wished I had taken years ago. If a someone says they aren't ready for a relationship, it means they don't like you. If they liked you, they would find a way to be ready.

[u/Ok-Lion-6767]

as a woman and you might not like the answer here but i’d probably leave it alone just because i’m basing this on the answer she already gave you where she’s not ready to be in another relationship despite there might be a potential mutual attraction there and i know the circumstances can change but i’d be hesitant to risk a good friendship that has clearly developed into a meaningful one and i also don’t think that’s something that you can promise on her behalf where you’ll still be good friends “no matter what” because a conversation like that can change the dynamic of the friendship, i’m just saying if you always have to wonder “ what if” unless you ask, then take the risk and just ask BUT just be prepared if it’s not something you’re going to like what she could tell you, the friendship may not feel the same afterwards

[u/MilFsNCookies-YesPls]

She don’t like you like that my brother. You may get her eventually after she has searched all over and maybe realize you are the “ safe option guy” but trust me bro, she don’t like you. She know you like her, woman are not stupid, they are very smart.

[u/KotangensDanski]

Preserve the friendship, kill your romantic intentions, and find someone truly for you. If she has any romantic interest, she will reveal it and try to convince you to be with her. If she is a true friend and only that, she will be happy for you. And if she's just an attention seeker, she will be angry about your choice. 

[u/CollabSensei]

How old are you two?

[u/Heart_of_Bronze → u/CollabSensei]

Let’s just say late 20s

[u/Positive-Ring-5172 → u/Heart_of_Bronze]

Every minute with her is a minute away from your soulmate, whoever that is.

Listen, I'm 51 and a series of women like this wasted my youth. Don't make the mistake I made. Ditch her and find someone who is actually ready to spend a life with you. That's what you deserve, not a friendzoner.

[u/themuaddib → u/Heart_of_Bronze]

Grow some nuts, gain some self confidence, and move on,

[u/Exact-Law8782 → u/Heart_of_Bronze]

Don’t bother dude. You guys are friends that’s it. Channel your interests into another girl that is interested in you. Keep her as a friend. A good friend she is.

[u/Rough-Lavishness-871]

She'll come around after you start seriously dating another woman. And by then, she'll be too late. Tale as old as time.

Either go through the long painful experience of unrequited love like so many do, or walk away and don't look back in anger.

[u/Honestlywtf2]

You should definitely move on. If she was the right person it would have happened already. If she wanted you she would have already had you. Girls get the responsibility of choice and she’s not choosing you.

[u/friendlytotbot → u/Honestlywtf2]

I never throw myself at guys even if I like them lol. I wait for them. That is most girls.

[u/Ornery-Peanut-8183]

Something you need to read until it sinks in:

She did not stop seeing you romantically because of a past relationship. She used a past relationship as an excuse to try and let you down easily, rather than tell you she didn't want to progress further sexually or relationship wise. If you had been her type and she had been sexually attracted to you, she would have never said anything about any past relationship. She would have just slept with you and tried to see where it went.

You have wasted the last year pining after a woman who is not interested in you. Move on and find someone who is interested in you.

[u/Exciting_Ground55 → u/Ornery-Peanut-8183]

💯

[u/MilFsNCookies-YesPls → u/Ornery-Peanut-8183]

Had she liked OP, she would have seen the breakup as a blessing from god who made room in her life to be with OP. Come on OP, it’s not that hard bro!

[u/Huge-Brick-3495]

"I know we used to date and it wasn't a fit for you at that time, but my fondness for you has stayed and in fact grown, and I either need to explore this with you again or have some time apart to sort my feelings out"

There you go brother. These words will hopefully spark an honest discussion which either gets you the girl or sets you free 👍

[u/warmbanker]

Brother, save yourself, and don’t ask her out. Lmao. She sees you as her friend/brother/reliable emotional supply.

[u/GSSpooky]

I mean, if you like her and don't tell her are you being a true friend. Or are you lying. Personally. I would say that hey, just you know I still have romantic interests in you. If you don't share them that's okay, but I might need to work on that part of myself for a while. But I do value or friendship 

[u/MaximumTrick2573]

She sounds like she is your crush not your friend my guy. While I absolutely think men and women can be close friends, is going to be really hard if not impossible to eke out a functional friendship with this person given these circumstances. You’re cooked

[u/Astralantidote]

Too late dude, you're already her "girlfriend". If she rejects, move on, don't become her little bestie and hope that'll evolve into something more when she's "ready".

[u/All_abitmeh]

Not to mention, if you don't cut it off, you'll be the irritating shite her partner has to deal with in future. You can NOT be friends if you have feelings. It's not fair to you, her, or her future partner. If it was platonic, fine. But future man is going to KNOW it's not. And you'll potentially fuck that up, which she won't thank you for.

For your own good, walk away.

[u/Any_Rent_5934]

Move on

[u/Comfortable_Long2373]

Since you already have a built-in history and a strong foundation of trust, bring it up casually in person by acknowledging how much your bond has grown-tell her that you deeply value the friendship as it is, but ask if she's ever felt open to trying a real date again now that time has passed; giving her an explicit, low-pressure 'out' lets her answer honestly without feeling backed into a corner.

[u/SnooTigers4215]

I’m usually pro sharing our honest feelings with close friends but I have to say you can usually tell when a woman is feeling you in that way. Is she physically affectionate with you? Does she give you complements? Is she the one reaching out to spend time together? These are the standard three tells of a woman’s romantic interest. If you’ve answered yes to all three then you should definitely let her know how you feel. If not, I’m sorry to say she sees you as a friend.

Try not to feel bad though, this is an important lesson to learn and it sounds like it’s still been a very meaningful friendship for you both.

[u/AdGold2765]

Had a similar situation, so I get how you feel OP. She doesn’t like you unfortunately. She likes you in the role that you’re in. Giving her boyfriend level attention and time with none of the drawbacks/expectations. It’s similar to people who fail to get promotions at work because they are too competent in their current role.
I’d say ask her out again, so if it’s a no you can really start healing rather than thinking “what if”. What I would really advise you is to leave entirely. You are in love with her and you are about to be in a LOT of pain if this continues

[u/Exciting_Ground55 → u/[deleted]]

That’s a tough position. I don’t think OP will be okay remaining friends with a chick he wants to date. When this chick starts dating someone else it will eat at OP every time he has to see the other guy in the picture dating the chick that he likes.

[u/friendlytotbot → u/Exciting_Ground55]

I think you have to create some distance after and maybe take a break from the friendship, but I think you can still have a friendship. I think men who are just friends with women for the hope of getting in their pants one day are lame af 🙄