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The man I love is has been dating a cute,...
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The man I love is has been dating a cute, waifish, blonde 18 year old *~*GaMeRgUrL*~* for the past few months whose main interests in life are CoD, peppermint schnapps and weed.

He and I are both in our late 20s and have been friends for almost a decade. In the past, we've had intense mutual feelings for each other, but they never panned out into a relationship to not being single at the same time and stupid, shitty behavior on both of our parts at various times when we were younger (one example: he felt I was flirting with one our close friends who happened to have strong feelings for me, so he got drunk and fucked a dumb cunt we both claimed to despise in my own house, and then I proceeded to date our friend partially because I felt heartbroken/lost and partially just to get back at him).

I know I'm his ideal physical type (brunette, fit, big ass) since he's told me as much, and our personalities mesh. We know each other's short-comings, mistakes and weaknesses, but we also know the best of each other. We push each other to try and be better people, and we have so much fun. We laugh so much every time we're together and just talk and joke for hours. He truly makes me happy, and it's no secret that we love each other "as friends" to those who know us. When we're alone, there is so much sexual tension barely being tempered by restraint. I haven't let myself be alone with him in a long time.

I don't begrudge him for wanting to be with a young girl who thinks he's "soooo, like, amazing, and, like, soooo hot." She's dumb and sweet, and actually adores me as something like a cool, older sister. I know with 0% input from me, this relationship will eventually fizzle out.

When it does, should I let him know that I think now is the time to try to make it work? Or am I deluding myself because I'm growing older? It never worked out in the past ... maybe we have too much history and have missed our chance already.
Maybe he's taken by a better mate. 2c
Very hard to say. In a lot of ways been there done that could apply, on the other why not just be straight up and, acknowledge the history and tell him you want to give it a real sincere shot instead of wondering about it.
Men don't really work like your last sentence. If you're attractive, you'll always be attractive. That's why the "friend zone" exists in some capacity. We thought you were attractive so we tried to get with you in some way. And some men just accept being friends.

Now the real question is if you even be attracted to him if he didn't have a gf right now? A -want what you can't have- situation.

Ultimately I think you can hold his torch and try to pick it up later when they break up or whatever, if that's what you want. But surely there are other guys you could see in the meantime. Do you really wanna be stuck with a gamer guy who smokes weed and is attracted to teenagers, into your 30s?
Hard to tell. You know the guy. 10 years is a lot.
Any particular reason you don't know if waiting or going for it now is wise?

Personally I'd probably be more into you if you told me during the relationship. Not because I appreciate cheaters or people who would like to break people up but rather because it shows you're more than just interested. It's not a small thing. And because you've known eachother so long he knows you're a nice girl who wouldn't want to cheat like that. If he wants to cheat deny him. It's not a win even if it will end the relationship they have.

If you've been good friends forever and he just got out of a relationship with a young girl then that's also a very good option. But I don't know what he's thinking.

Does he have any reason to think you're interested in him in that way? I personally don't see the attraction to a girl like that (if she's as you describe). But you're describing a stereotype mostly.
The other question is if the sexually tension is purely on your side and his desire is imagined by you.
Are you attractive?
You can drop hints to see how he responds.
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you want the guy who got away from you,

>you dont love him: its lust

if you did love him most people would have said something by now.
remember right now he only sees you as his friend nothing more.

you going to have to wait and see when or if they break up. how are going to feel if he ends up marrying this girl?
you need to have a back up plan for yourself.

i wouldnt drop hints to find out "how he responds" most guys dont do hints and even if he does respond he will just regard you as his bit on the side while he is screwing this other girl
Could be. He doesn't seem very happy considering he still flirts with me, but who really knows how things will end up.

I worry that doing this again when we're both finally in more "adult" places in our lives will take a toll on our friendship.

I would still love him and want him if he was single. I would probably be just as afraid to start something with him though.

I think if I I date other people in the meantime, he'll eventually become single, then I'm the one in the relationship, and finding out if we could work will once again be put off continuing this stupid cycle. As far as his attraction to this girl (he actually doesn't smoke at all or game very much) -- he's got his flaws, I've got mine too.
>because I'm growing older

How old are you and this guy?
>>How old are you and this guy?

Sorry OP...just caught it in your original post.
I don't really want to be the impetus that drives their relationship apart, which is why I'm hesitant to bring it up now. Because we've had so many crappy false-starts, I would want things to begin on a positive note.

He knows I was very interested in the past. Now, I'm not sure what he thinks.

This girl is uncomplicated and pleasant -- just on the simple, immature side. She could change as she ages, I'm sure. He started dating her shortly after I was in a relationship of my own.

He's told me I'm beautiful/sexy/hot. I've told him that he's got a fantastic body, expressive, elegant facial features, and the most wonderfully colored eyes. We've said that we love each other. We have kissed in the past as well, and I felt his erection pressed into me long before then. But nothing ended up in a relationship due to dumb behavior from both of us.

We've said things before, but it didn't work out at the time due to both of us doing stupid things, maybe self-sabotaging, maybe just being stubborn and immature.

If he marries her, I'll move on. Sure, I'll be incredibly hurt, but he is still my friend. I don't want a back up plan right now .... I want to give this a chance. In the past, I always had a back up plan, as did he, and we've ended up dating other people because we didn't want to wait. I think I want to wait this time. It still might go to pieces, but it deserves me trying with all I have, right?
so you are one of those: i dont want to be in a relationship when he is single types.

stop hanging on to this ideal that him and this girl will break up, they may have a lot in common and like i said may end up marrying each other...
then whose going to feel like the bad guy?
do you really want to be in your 30s waitng around on somebody who may not even be comming back?
In your head you probably think he's the best guy and you would be so happy with him, but it's just a fantasy over something that may not even exist. If not being with him is making you sad then it's unhealthy. You should lower your contact with him to really find yourself, because right now you're just going to get more infatuated and it won't be good. And I'm not trying to be a bad guy when I say that, it's personal experience, and it's not your fault.

Meet other dudes they are fucking everywhere. Date some, you don't have to be in a relationship, just date some you like, this didn't make you a slut. Maybe you will find friends or fuckbuddies or lovers, which is more than what you can get from him. This is win/win for you and it might even make him see you in another more seductive light. But you're not doing it for him, for yourself. You deserve to feel intimate love.
You and this guy sound like you get your dating life based around friends. Friends is a tv show, it's not meant for people to emulate that sort of behaviour in real life, both of you need to grow up and realize that if you're in the late 20s.
I know a woman who is almost 40 and waited... she's still waiting and has never had kids or a family because of it. If he wanted to be with you he would. He has chosen other girls and you are in friend zone. You should let go before you lose your chance at a happy life. Why wait around for being second choice? And eventually the girls he's dating will most likely not like you and he will ditch you for them anyways. So no point in wasting any more of your time before you're also 40, single and lost the opportunity to have your own family. Especially if he's telling you how much he likes her and how hot she is, you mean nothing romantically for him, that was your hint so take it
In the past, I've pretty constantly been in a relationship, so I wouldn't say that's my "type." This time, I'm considering not doing that.

I don't think I'd wait for years and years for him, but I feel their relationship is ending pretty soon since I've heard from other friends that they fight all the time, and they don't connect very well.

I have dated and been intimate with other people during and before the time we've known each other, as has he. I'm not a lonely virgin wanting him to save me, I'm trying to see if we're ready to finally try, instead of being impatient or scared.

Haha ... unintentional emulation. I am still growing up. He is too.

I have no intention of waiting forever.

He has never told me how much he likes her or that he thinks she's attractive. He has actually not said that to any of our friends, just that she's his girlfriend. He's not really discussed any of his feelings about her with me. I don't ask either. She has told me a lot about her feelings for him though.

And he has told me that he thinks I'm attractive and amazing in the past, but during times when I was in a relationship with someone else or not at a good point to start a new one.
if you guys enjoy hanging out so much, go hang out, watch a movie, eat something, and if there is so much sexual tension, it will happen
and if it turns out to be good, this will turn automatically into a relationship
and this is the best way to start relationships. letting it happen

don't rush it with a "i'd like to try it with you" because then you put so much expectation on it in a way you'll never fulfill.
letting it happen makes it feel like you're over accomplishing all the time.
Anon you really can't wait around. You have to gauge how into this girl he is. If it's not much you could tell him how you feel about him similarly to how he told you. If you don't know what he feels then this is just a waste of time at best. Do you think he will like you more later? There's two cases. There's the case where he really likes her. That's where you lose no matter what unless she gets rid of him. (if you're quite fiendish you could make that happen maybe, but I don't recommend it). If that's the case then you'd rather have time to spend elsewhere right? It doesn't make sense to wait until they're engaged if that happens. You're a friend, it's not an odd thing to ask. If he doesn't like her much at all there's many options. But at least you know the window is open. You don't have to worry as much and can relax better. If he's not heavily invested you know how ok it is with the sexual tension and stuff (it's not good to be the person he's trying not to cheat with). You can even act upon it if the moment arises. It's good information to have simply.

Also just asking is a candid show of interest. I'd consider it a positive. Because we judge who to stay with based on our options and I'm not sure if it's well conveyed that you like him in that way since you feel you want to tell him. At least make it an idea for him.
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