How to try and finally get out of the friendzone?

[JST8828]

For the better part of almost 16 years up until the pandemic hit in 2020 and we lost touch, since our high school years I was friends with a girl I always had a crush on since day one. So a lifelong crush you could say, and one that somehow someway I never truly gave up on. I met her when I was 17 and she was 15. Occasionally put her on a pedestal, occasionally didn't, its been a roller coaster of a friendship. I was just always extremely attracted to her from the start and there's not much else I can say to explain. I'm 40 now btw, while she's 38. I was a full blown AFC when I was a teen and even well into my twenties, so I never really stood a chance with her anyway. As we got older I'd end up seeing people, as would she, but in between there would always be little subtle attempts at me trying to make something happen with her, all which led nowhere. She even befriended a long term 2 year girlfriend I once had back in the early 2010's. She was part of my friends group. She was just always there. It should be noted that almost every single guy she ever dated would treat her like sh-t, and I always had to sit back and watch it, shaking my head in the process until I finally just had a "f-ck it" type of attitude towards her as I reached my late 20s. I pretty much accepted friendship with her at this point too, but always kept my distance to a degree because of how difficult it was to be around someone I felt such a strong attraction to. To be clear, while we absolutely got along very well and have had a lot of fun over all these years which she knew and acknowledged, we would fight quite a bit too. Many of our friends always felt like we could have or should have been a couple, specifically at a wedding one night in 2018 where we were pretty much each others unofficial dates and danced with each other throughout the night.

Finally in what I beleive was late 2018 at the age of 34, when I was now much more mature and began perfecting my game, for the first time ever, on a few occasions she began entertaining the thought of possibly dating me. It was almost as if I felt like her failures in dating douchey guys in her younger years woke her up and now before it was too late she was maybe going to give things a chance with us. She explained how she'd be open to spending more time with me and sleeping over without sex to see how she feels, etc. All of these occasions of her talking about us dating would lead to her a few days or week later when she'd be back saying how she just views me as a friend. I did nothing at all to spark this and many times didn't even communicate with her in between. This was just how she was for years and years. Always reminding me that I was a friend and never being able to see past that. In reality, while I've always treated her amazingly and she's been thankful for that, I always felt that for the most part the thing was that she was never physically attracted to me. This was reflected in the men she would date over the years. They didn't look much like me. I'm a relatively decent looking guy for what it's worth. I'd give myself a 6 out of 10, whereas I'd put her around a 7.5.

So as the pandemic hit we finally kind of grew apart, only occasionally keeping in touch through small instagram DM's. She got married in 2023 and I felt that was the closure I needed. Wouldn't you know it though, and to my honest shock, in a little over a year after the wedding in January 2025, they split. Turns out he treated her horribly and wasn't the guy she thought he was. She's no saint, but she gave me many examples that really painted a picture of how awful this guy was. I know this bc I reached out to her in January and offered the info. The rest is history as over the next two months we reconnected nicely, even apologizing to each other for the few times we'd fight back in the day. We met for drinks a week ago and saw each other for the first time since late 2019. It was a really awesome night and a bit surreal to be back out seeing her. She looked hot as hell of course, even telling me that she got her hair and nails done today. I joked with her saying I'm flattered, even though if pressed she'd probably say it wasn't for me, and of course I went the extra mile in trying to look my best. It was nice reconnecting as now more older and mature adults, enjoying drinks and laughing and conversing for nearly 3.5 hours both at my place and then a local bar. As a woman who just recently had a dramatic split from her husband, I only briefly mentioned something about the idea of dating for us, telling her that I "Of course you're an awesome woman, but I cannot relive the 2000's and 2010's with you and all I ask is that you just keep at least 1% of an open mind with regard to the two of us". She didn't say anything back but instead just smiled. She then started going on about all her shortcomings and how I wouldn't want a woman like her and how we might not be a good match (i.e. she's messy, I'm neat, etc). She's done this in the past as well.

The conclusion is simple though- I'm going to ask her to come over for dinner one night soon and will ask if she thought about what we talked about (i.e. the 1% thing). I'm not going to press her or put any real pressure on her, but if she starts in with any friends only talk, that will have to be the end and I will have to finally walk away for good, which I'm fine with doing. That is the difference between who I am now and who I was years ago. While I do have this small afc-like idea in my mind that everything thats happened between us maybe leads to this and we finally get to try dating, I also know thats rather unlikely. But what I definitely know is I will be able to walk away in peace. I already did that for a few years anyway when we lost touch and she got married. I know for certain that the thought of dating me still lives in her head at times, even if its miniscule. I guess my only question is, how do I get her to become more comfortable with it in the event she actually makes it seem like she's open to cracking the door of dating open with me, what could be the best possible ways to turn a long term friendzone situation into romance? Seems like a slippery slope especially with this one, but I'm still confident it could be done. Thanks in advance.

 

[Mike32ct]

Sure, ask her and get the closure you want. Then move on.

I’m sorry, but the probability of this resulting in you two dating is very, very close to zero. I’ve been there and learned the hard way.

She’s had many, many opportunities to date you, but she hasn’t availed herself of any of them.

The friendzoned guy is almost never the backup guy. No matter how many times she becomes single due to breakup, divorce, etc., the woman almost never starts dating the FZ guy.

 

[Smartone84]

I wouldn't get too caught up on thinking she's not physically attracted to you. We all know that's never a big thing with women as long as you have some game as well as something to offer them (i.e. serious money, stability, the ability to make her a mom, etc)

The likely scenario was your pushy AFC tendencies over the years ultimately led her to viewing you only as a friend. Sure you are more older, mature and wiser now as you say, but it really is probably too late. As @Mike32ct said the overall odds of you guys dating now are just so low.

 

[Mike32ct]

If you’re in the FZ too long, you become her brother. You have comfort and emotional connection, but without the mutual romantic/sexual connection.

And even though it might seem quite logical for her to start dating her best guy friend, that thought will typically give her the “ick” because it seems/feels incestuous to her at that point.

 

[Pandora]

An older dude told me in my 20s that the best way to get out of the friendzone is to get serious with another girl and bring her around.

Women are nuts and there are different types of friendzones. You got the friendzone where you are disgusting and she would never touch you. You also go the power play friendzone in which she is keeping you for her own little purposes ( marriage options, attention etc).

Get another girl and treat her well. You will see her true colors then.

 

[Pandora]

Regardless you dont want this girl for a LTR. She will never love you like how you deserve. If you just wanna smash then ok.

 

[JST8828]

Regardless you dont want this girl for a LTR. She will never love you like how you deserve. If you just wanna smash then ok.

My plan is to explain to her how I'm not looking to marry her, not even looking to date her, but again, to just have her leave a little piece of her mind "open". Ultimately what I'd hope for is a casual dating thing that would eventually include sex with the (likely small, I know) possibility that it could end up growing into something more one day. She did just leave her husband after all. Divorce not even close to being finalized yet.

 

[Pandora]

My plan is to explain to her how I'm not looking to marry her, not even looking to date her, but again, to just have her leave a little piece of her mind "open". Ultimately what I'd hope for is a casual dating thing that would eventually include sex with the (likely small, I know) possibility that it could end up growing into something more one day. She did just leave her husband after all. Divorce not even close to being finalized yet.

Hey you might be able to get some sex. I hope you do. That would be cool.

I do know with 99% certainty that you dont want to date her. She will resent you because you were not her first choice.

If you get her pregnant she will 99% leave and screw you over. Unfortunately with women if you are not her first then you might as well be her last.

Dont you think you deserve a woman that worships you from the first time she saw you? Or you deserve to be someones 9th choice.

Im not trying to be mean.

 

[Clockwerk50]

It must have been exhausting living in this headspace for 16 years, almost as exhausting as writing this and reading it.

We could argue that you’re still somewhat beta, not just because you’ve spent years seeing this woman as some kind of unicorn or the protagonist of your personal romantic novel, but because if you had options and were getting laid regularly, you’d see this for what it is: you’re not getting what you actually want, sex. Having other women in your life would keep you from developing oneitis over this girl, especially with the number of red flags and how long you’ve been interacting with her with the intention of being more than friends. This is the epitome of a “nice guy.” You’re currently focused on her, and that focus is preventing you from seeing things more clearly.

I know this is just a synopsis of the 16 years interacting, your feelings, her behavior, and how much they fluidly changed throughout the years. However, I will try my best to give an objective analysis on a couple of things you wrote:

1. You are a 6, she is a 7.5. In this case, she is dating down, and you are dating up. The general rule is that men date down and women date up.

2. “Every man she dated treated her like ****” and “[her husband] turned out to treat her horribly.” She is 36. Why is this a red flag? Because repeated bad relationships suggest a pattern. Either she is attracted to toxic men, or she plays a role in the dysfunction. At her age, she should have learned from past mistakes.

3. Femininity is the relationship-based gender, while masculinity is the conquering gender. In this dynamic, you are the one constantly trying to make the relationship work, analyze every interaction, and rationalize her behavior—this is a feminine trait.

4. She said, “You wouldn’t want a woman like me, and we might not be a good match.” This is tempting because it creates psychological tension. “The most effective way to seduce is to be unavailable.” By presenting herself as out of reach, she triggers your desire to prove her wrong, making you chase. This keeps you hooked while she gets what she wants from you, whatever that may be.

5. You used the word “even” a couple of times. It signals that you’re overly focused on what she’s doing, which can show emotional sensitivity and difficulty accepting the reality of her current level of interest. What matters most is her present actions, not past interactions. Stop overanalyzing and let her show you where she’s at now.

With all these factors, whether you choose to continue pursuing her, stay friends, or step away is up to you. However, if you want any chance at this working, stop idealizing her, identify the emotional gaps she needs filled, see the world through her eyes instead of leading with your own desires, and have a more masculine presence to guide her into a world of pleasure.

As an example, if you are looking for comfort and stability and offer them to her, or assume she wants this because you do, you will be creating the opposite effect. Pay attention to what she lacks, not what you want to give.

 

[JST8828]

if you want any chance at this working, stop idealizing her, identify the emotional gaps she needs filled, see the world through her eyes instead of leading with your own desires, and have a more masculine presence to guide her into a world of pleasure.

The problem with her right now is she is fresh out of a marriage (even if it was going downhill from the start) and the emotional gap she needs "filled" would really to be to just have fun and be distracted from the tough time she's going through. I can give her that of course with fun nights out and whatever else, but at the same time I don't want to create this vibe of friendzone city with her. I want to try and be there for her during this weird time in her life while also showing her that I've changed and can actually be a potential suitable partner for her in time.

Bottom line though is (and this is if she even agrees beforehand to be "open") I really want to try and set a tone quickly with her so it doesn't go that friendzone route. This is tough because I don't want to come off as pushy, but I again, I don't want to fall back into the friendzone by default after multiple platonic type hangouts. By setting the tone of course I don't mean that I need to have sex with her on outing number 2 or 3, but something as simple as holding her hand or being a little touchy at the bar I'd feel is a necessity to break down that barrier of 16 years of friendship. While we knew each other 16 years, don't forget we hadn't seen each other the last 5 years, so really we are at 21 years total, but its been so long since we've interacted and been friends that this could really be some sort of fresh start.

 

[Chow Mein]

The reason why most are in the friend zone is that they didn’t make that move from the very beginning, leaving the girl wondering AKA letting her think of all the reasons not to be intimate with you.

My experience is that you leave trails and nuggets if you think you’re FZ’ed to see if she bites. Just text pictures of what you are doing with your life. Sometimes they do, most of the time they don’t. Doesn’t hurt because you are coming off in the same friendly manner, but she knows what you’re up to. If she’s at a point where she is available, she’ll follow along.

@Mike32ct is on point, don’t invest too much time into making it out of the FZ. Slim chance, but heck you put in minimal effort.

 

[Clockwerk50]

The problem with her right now is she is fresh out of a marriage (even if it was going downhill from the start) and the emotional gap she needs "filled" would really to be to just have fun and be distracted from the tough time she's going through. I can give her that of course with fun nights out and whatever else, but at the same time I don't want to create this vibe of friendzone city with her. I want to try and be there for her during this weird time in her life while also showing her that I've changed and can actually be a potential suitable partner for her in time.

Bottom line though is (and this is if she even agrees beforehand to be "open") I really want to try and set a tone quickly with her so it doesn't go that friendzone route. This is tough because I don't want to come off as pushy, but I again, I don't want to fall back into the friendzone by default after multiple platonic type hangouts. By setting the tone of course I don't mean that I need to have sex with her on outing number 2 or 3, but something as simple as holding her hand or being a little touchy at the bar I'd feel is a necessity to break down that barrier of 16 years of friendship. While we knew each other 16 years, don't forget we hadn't seen each other the last 5 years, so really we are at 21 years total, but its been so long since we've interacted and been friends that this could really be some sort of fresh start.

If she’s unhappy and not content with her current situation, someone may easily step in to fill her gaps. You may be right, she could be needing excitement and adventure, but there are other needs too, like feeling desired by a masculine man, emotional validation through being understood and supported, intellectual stimulation through meaningful conversation, or appreciation for her qualities, such as her intelligence or creativity. There are more, but you know her better than anyone.

As for not falling or getting out of the friend zone, it all depends on how you interact with her, how you talk, behave, lead, and impress. Unfortunately, it’s too broad a topic for one post, and some things in the micro behavioural level cannot be explained, only internalized through trial and error. Ultimately, you can’t seduce everyone, and life’s too short. A good hunter knows to play the odds. If she doesn’t reciprocate, or in other words, doesn’t want to play ball, just move on and keep leveling up. After all, you cannot negotiate attraction, and there are no magic words to initiate it. All you can do is have an attractive look and personality and see if any fish bites.

 

[Vanderdonck]

OP, some notes.

It's possible to get sexual with her but you have to BE sexual around her. That means no boyfriend vibes. You have to have the vibes of a guy with options. I don't care how old she is or how exhausted she is. She probably is attracted to you on a base level but you have spent two decades mitigating that with cheesy simp behavior.

Second, women will put themselves in relationships with the guys they think they deserve. She is a chick who thinks little of herself and lo and behold, she dates losers. This part is no reflection on you. You're probably a good guy and she thinks she could never have you (or a guy like you) - she said as much. Believe women when they say this stuff. There are other women out there with more self confidence who see a great guy and think "I gotta have him." And they often get him. Lots of women in between of course.

This girl you speak of, believe me, I know her. She leaves just enough clues for you to think it's possible but throws up the shield. This is because of your value relative to her perceived value. (That and you simped years ago and set a tone.) You can date other women, make all the right moves and she will still likely reject you.

You COULD go for broke and confidently say "I don't want to be friends." Be prepared to lose her. Small chance she comes around. But if I were you I would also think about how a relationship with her would actually work. Or if you just want the sexual conquest because it's been so elusive. Is it limerance? As others above said, stop idealizing this woman. Remember she's just a chick with exes who are tired of her like everyone else.

 

[zekko]

An older dude told me in my 20s that the best way to get out of the friendzone is to get serious with another girl and bring her around.

It's interesting that it seems so easy to just get serious with some other girl. I guess it's the attitude that you are simply using this girl, and have no real investment or emotions for her that makes it so easy. I'd say use that tactic to find a girl (since it's so easy), and then open up your eyes and see what you have.

 

[Pandora]

It's interesting that it seems so easy to just get serious with some other girl. I guess it's the attitude that you are simply using this girl, and have no real investment or emotions for her that makes it so easy. I'd say use that tactic to find a girl (since it's so easy), and then open up your eyes and see what you have.

I have used this tactic before. You find a date and bring her around. The girl that put you in the friendzone will get pissed. If she does not get angry then you have no hope. I agree it is not right to use the other girl. I probably should not have said get "serious".
Its hard to explain but if done correctly no one gets hurt lol. It just a barometer check. Dont ditch the girl that likes you. I agree Zekko.

 

[Vanderdonck]

It's interesting that it seems so easy to just get serious with some other girl. I guess it's the attitude that you are simply using this girl, and have no real investment or emotions for her that makes it so easy. I'd say use that tactic to find a girl (since it's so easy), and then open up your eyes and see what you have.

See what you have and that what you chasing before wasn't such a good fit.

 

[JST8828]

She is a chick who thinks little of herself and lo and behold, she dates losers. This part is no reflection on you. You're probably a good guy and she thinks she could never have you (or a guy like you) - she said as much. Believe women when they say this stuff.

Yes, I am a good guy. Great in fact. But those types of guys typically finish last, right? It's just a fascinating thing because when I look back at when we were in our teens and 20s, I think of her as so much younger and naive, so maybe it was just that young foolish phase for a chick. Now she's 38, fresh out of what was basically an abusive marriage and seemingly still completely against viewing me as a potential partner. A big part of that were those 16 years of friendzone life and another big part of that, while I almost don't want to admit it, is the fact that she really is likely a bit of a headcase who only attracts douchey guys. Just a sad reality, but I think its a reality for a lot of women.

You COULD go for broke and confidently say "I don't want to be friends." Be prepared to lose her. Small chance she comes around. But if I were you I would also think about how a relationship with her would actually work. Or if you just want the sexual conquest because it's been so elusive. Is it limerance? As others above said, stop idealizing this woman. Remember she's just a chick with exes who are tired of her like everyone else.

To be totally clear, while she's a very special woman to me, I no longer idealize her. Never really have in a very, very long time. I accepted the friendship dynamic as way back as my late 20s/(maybe early 30s) and let her go and "lost" her completely for years even before she ended up married. And guess what, I am 100% prepared to lose her again, even after this super nice/nostalgic/awesome reconnection we've just gone through. Life is simply too short and I am no longer that guy who longs for a woman that has no interest in me. Will I be disappointed? Yes. I will. But considering by no means is this my first rodeo with her, I'm pretty sure I'll be over it within 24 hours. Maybe a little longer considering this will likely mark the absolute end of any kind of relationship or communication with her for the rest of our lives.

As far as thinking about how an actual future relationship would be, at 40 years old and now what I feel is fully matured with regard to understanding connections and women's personalities mixed with mine, I truly wholeheartedly beleive it would be awesome and a lot of fun. I feel like there is so much untapped potential for her and I that it really is a little sad to think that she may just completely shut any thought of anything with me down. But I won't be able to change that. I'll just be able to walk away. It's her life and her decision. I don't want to say she'd never know what she's missing out on, bc after all these years I know she's well aware of how great of a person I am and how well I treat her, but it's her life. If she wants to live it alone or with another potential douche down the road, then so be it.

emotional validation through being understood and supported, intellectual stimulation through meaningful conversation, or appreciation for her qualities, such as her intelligence or creativity. There are more, but you know her better than anyone.

One interesting thing is that I've told her and she's seen so far, is that I changed a lot in these last five years in terms of how I behave, react and listen to women I interact with. I used to be a little harsh with her at times. Would critique her decisions and make her feel bad sometimes. I've told her thats no longer me and she's told me she's seen that in just these short two months of reconnection. There still may be a dead end ahead of me but I'd like to think this all could definitely help my case with her.

 

[Vanderdonck]

Yes, I am a good guy. Great in fact. But those types of guys typically finish last, right? It's just a fascinating thing because when I look back at when we were in our teens and 20s, I think of her as so much younger and naive, so maybe it was just that young foolish phase for a chick. Now she's 38, fresh out of what was basically an abusive marriage and seemingly still completely against viewing me as a potential partner. A big part of that were those 16 years of friendzone life and another big part of that, while I almost don't want to admit it, is the fact that she really is likely a bit of a headcase who only attracts douchey guys. Just a sad reality, but I think its a reality for a lot of women.

Being a great guy doesn't mean you're a doormat or finish last. Depends on how you project yourself; that's a whole other conversation.

A lot of women go through the bad guy phase in high school. Some just don't break the habit. Thirty eight is pretty old to still be learning that lesson.

It sounds like you have the right mentality. Let her do what she wants. You do you.

 

[The Duke]

@JST8828 all these years later, you are still too afraid to take life by the horns and go after what you want. Thats why you never win with her. She see's that weakness in you. She wants a man, not a woman. Your approach is very feminine.

I had a girl I dated for a while that gave me the "let's just be friends" speech at a bar one evening. After listening to her for 5minutes, I stood up, dropped some cash on the table, ready to leave and told her that i wasn't interested in just being friends with any woman. It changed her mindset immediately. She jumped up and straddled me with her legs and said that was the hottest thing ever and she needed to hear that. Got a few more months out of that ride.

You need to come right out and tell her you aren't interested in simple friendship, you want a romantic relationship or you need to go separate ways.

I can tell you by what I've read, you still aren't the right guy for her. You lack moxie.

 

[JST8828]

You need to come right out and tell her you aren't interested in simple friendship, you want a romantic relationship or you need to go separate ways.

This is basically my plan, as I wrote. It'll happen in a phone call before I even committ myself to another outing with her. Yes we initially went out and caught up, had an amazing time, but I did feel this one night needed to take place in order for us to feel reacquainted with each other after so many years.

@JST8828 all these years later, you are still too afraid to take life by the horns and go after what you want. Thats why you never win with her. She see's that weakness in you. She wants a man, not a woman. Your approach is very feminine.

You're acting like my plan or my actions are somehow dead wrong. She literally just got out of a marriage and has made it known to me multiple times that she has no intention of marrying again or at least anytime in the disant future, and she feels the same about dating as well. Hence my comments to her about just being "open" a very little bit for now. I went out with her to show her a great time as well as how much i've changed and how well i'm doing in life. Not to scare her away on night one by telling her I want to be with her. Mission was accomplished and i'm satisfied with the night. She had a great time. Now, as much as she'll likely be very upset about it, I'm going to tell her she either needs to be open to more than simple friendship with me or I have to walk away unfortunately. I have no hesitation or second thoughts going into this.