I Have a 20-Year-Crush on A Man, And He Still Hasn’t Asked Me Out!


I have read everything on your site, and no story matches mine, so here goes. I met the love of my life twenty years ago on a professional basis, and I knew right away that I was in love. We never became involved, only really good friends. He went on to marry someone else as did I, but we remained great friends with amazing chemistry always present. We have never been intimate; although, we did share one passionate kiss he initiated many years ago following a company Christmas party.

I am recently divorced, two years after he divorced his wife. We now talk a couple of times a week, and it is killing me that he has not asked me out. I compare all the other men I meet to him, and of course, none of them measure up. We have told each other that we love each other, but it never seems to evolve into more than just a platonic relationship.

Meanwhile, the men that are chasing me don’t have a chance because I am stuck in this torturous place, in love with my best friend.

We have seen each other through so much, and we are very supportive of one another. We talk about everything under the sun. But…it never seems to evolve into the whole enchilada. I have tried, several times, to cease contact with him so I can focus on another guy, yet he always calls and rekindles emotions in me. What do I do?


Dear Maria,

If you’ve read everything on this site, then you’re definitely familiar with the concept that men do what they want.

Now, of course, nobody actually thinks that this advice applies to them. It applies to other women who refuse to see reality. But not you, your relationship is different.

And if they’re not doing what you want them to, you have two choices: stay or go.

Now, of course, nobody actually thinks that this advice applies to them. It applies to other women who refuse to see reality. But not you, your relationship is different. Your feelings are real. Your chemistry is palpable. You’re in love.

Hate to say it, Maria, but splash some cold water on your face and wake up, you’re living in a fantasy.

Let’s start with your first line: “no story matches mine”. Really? I would say that about fifty percent of the emails I get come from women who are dealing with some form of unrequited love.

I’m looking through the archives right now: I Moved to Be With My Long Distance Boyfriend and Now He Ignores me

I Still Sleep With My Cheating Ex-Husband

I Love My Ex-Boyfriend, But He Only Calls Me When He Wants Phone Sex

My Catholic Boyfriend Refuses to Have Sex With Me. Should I Try to Seduce Him.

My Ex Keeps Promising to Commit, But He Never Follows Through.

And especially, this one: This Guy Loves Talking to Me But Does Not Want to be My Boyfriend

Are you getting the idea? Your story, Maria, is the most common story on Earth, the woman who is convinced that the man has equally strong feelings from her, except he’s just not acting on them, dammit!

Do you know how this sounds? It sounds to me like you are finding all the evidence you can to support your hypothesis (we have chemistry, we kissed once, he loves me platonically), except you’re ignoring the one thing that blows your hypothesis out of the water: He Hasn’t Asked You Out!

And if he’s been talking to you twice a week, in a period when he didn’t have a girlfriend, and he STILL hasn’t asked you out, guess what? He’s not going to. He thinks you’re nice. He thinks you’re cool. He thinks you’re safe. But unless he’s taken a secret vow of celibacy or has been trapped under a refrigerator since 2006, there’s nothing preventing him from asking you out.

Except for the fact that he doesn’t want to.

So if you’re perfectly content being in love with your best friend and not giving any other guys a shot, keep on doing what you’re doing. But if you ever want to find true love, by which I mean the reciprocated kind, you’re going to have to do these two things:

But unless he’s taken a secret vow of celibacy or has been trapped under a refrigerator since 2006, there’s nothing preventing him from asking you out. Except for the fact that he doesn’t want to.

1) Get out of fantasyland and realize that you’re not in love. You’re infatuated. Your chemistry is far stronger on your side than it is on his. If you still doubt me, remember: if he felt the chemistry that you feel, don’t you think he’d ask you out?
2) Slow down communication with this guy so he doesn’t have such a hold on you.

The more you treat him like a boyfriend, talking all the time, putting him up on a pedestal, the less time you have to devote to finding a guy who ACTUALLY feels romantic feelings toward you. If you need to cut off entirely, so be it. A good guy will understand that you need to go your own way to find happiness. Just don’t expect him to cut you off out of compassion, he likes you too much as a friend.

Finally, please own up to the idea that your story is not unique. The only thing that’s unique is that you’ve believed your version of events, you and this guy should be together – for 20 years.

Time to let it go and move on.

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  1. 21

    I also agree with Cinnamon. Pulling back to move on from a crush is healthy. Doing so with the hope of forcing the other person into some kind of action is game playing.

    Yes, it is more likely than not her friend just isn’t interested in a romantic relationship Maria after all these years. But…it IS also possible that yes, he has trained himself over the years not to think/react to her in that way, or also possible that he has gone on believing all these years that SHE didn’t ever think of him in that way.

    I know it’s possible, because I didn’t have the convo with my friend until after 10 years, and we both admitted to having “the thoughts” but never mentioned it to each other for those very reasons.

    Bottom line: you will never know until you ask. And after 20 years…? Wouldn’t you feel foolish playing games with such a close friend?

  2. 22
    The Seductress Within

    Cinnamon, Yes, I see what you meant now. There is a difference. One that would be freeing for her and one that would keep her stuck in this place longer.

  3. 23

    cinnamon, Steve et al,

    By ‘pulling back’, I’m not suggesting game-playing. I’m suggesting she look after her own heart/interests, step back and realize what’s going on.

    Guys are creatures of habit. If she continues to be there every time he calls, she’ll remain in the same rut pining away for him and he’ll consider her the same friend. But if she’s not there, he’ll notice, and miss her, and if he does have feelings for her, at this point he’ll notice. But she can’t expect that, she’s gotta do this for her, have a chance to consider her own feeling and move on.

    Of course, she could tell him straight out how she feels. But – and I’ve heard this a million times from my guy friends – actions speak louder than words and guys often only hear what they want to. And it probably won’t solve anything because she obviously has feelings for him and he’ll continue to behave the same way.

    I’ve been there where I dated a guy who wasn’t ‘ready’ or couldn’t commit, etc. And every time I tried to be direct and honest I got nowhere. It was only after I stopped returning his calls when he noticed. But after having to do this too many times I finally just cut the cord.

    I’ve also been on the other side, w a guy friend who liked me, but I didn’t feel the same way. We were honest w each other. He then stopped calling me/didn’t return my calls. I was hurt and missed him but understood. His actions didn’t cause me to change my feelings for him but it did make me respect him more.

    So perhaps you can view this as a game, but I see it as acting out of her own interests. There’s no way a guy would put up with this, so why should she?

  4. 24

    “Actions speak louder than words.” 65% of communication in a relationship is “BODY LANGUAGE.”

  5. 25

    Well I guess it all depends on what you’re looking for in a relationship. I, personally, do not want to be in a relationship where not answering calls is used to communicate “I want you to commit”, “I want you to spend more time with me”, “I want you to give me more attention” or “I want you to have sex with me”.
    If that was the kind of communication I was subjected to, or if that was the kind of communication I would have to restore to to get through to the guy with something I already openly asked him for, then I would seriously reconsider if I’ve invested my feelings with the right person. As you experienced yourself, it only works short term.

  6. 26

    Maybe that is the problem… he has been putting up with it for 20 years. What is his story? Did he get tired of waiting, that is why he got married to begin with? Maybe he felt she was kind of there for him but maybe not, like mixed signals. He might not know where he stands with her at that level, so he does not take it seriously.

    After 20 years, maybe he gave up on ever having something romantic. If she never voiced her concerns about her strong desire in the past, then why would he think about them now?

    I have heard a number of women say that guys are clueless when it comes to knowing if someone has a crush on them.

    After reading what everyone else has wrote, I say jump in feet first. If it happens, then it happens. Never look back with regrets as to if it might have happened, or it could have gone a certain way. It is either or either not.

    Go up to the guy, whisper in his ear that you have always had a crush on him. Next drag your nose across his face so that barely rubs on the skin, then give him a peck on the lips, closed mouth. Get it done and over with. You have waited 20 years, why wait another 20 more? If he does not have the same feelings, move on and have your next 20 year crush.

    For me, I can can go years where I do not get sleep and I am always running behind. I have just gotten to the point where time is short and I can never get enough done. I have no problem going up to someone and being blunt.

    It might even be best to do it cave man style. She should just drag a club behind her, point at the guy and say, “me you couple, now”. Then hit him with the club and drag him home. At some point, if you want something to happen, you are going to have to be aggressive about it. Nobody is going to make things happen for you, except you.

  7. 27

    And Steve, to get back to your question about women who are affectionate among guys, it could be a test but I agree w you & Thomas, women like this are often just in it for attention. They could be acting this way because they feel safe with the guy as a friend so their guard is down, or they’re just flirty. I had a friend in college who was always flirty w guys, touchy/feeley, etc. Some of them took her up on her offer, only to be rejected. Others saw what the women at the sidelines saw, just a tease.

    But it doesn’t sound as if this is the case with Maria.

  8. 28
    Michael Ejercito


    Why do you not ask him out?

    Do you expect others to wipe you after you use the toilet as well?

  9. 29

    I wonder – and I’m not being critical just putting the question out there – if Maria receives some sort of emotional “payoff” by holding on to the unrequited longing for lo these 20 years? It may be some sort of comfort zone thing. Evan has a way of getting right down to the bottom line of things; it is the truth and the truth shall set ye free.

  10. 30

    cinnamon, I’m actually repeating what Evan has advised in his previous posts – i.e. “if you don’t like how you’re being treated, then leave.” “Best advice, do nothing.”

    By oontinuing to speak with a man who does not seem to be reciprocating her feelings, Maria needs to be honest with herself and ask if she wants to continue hoping for something that may not happen She could either tell him outright how she feels, or just cut him off and move on. Otherwise it’ll be the same cycle.

    My point in mentioning my experience wasn’t that I was hoping for a committment by holding back. It was that, after directly speaking with him about an issue, but not getting anywhere, not being his convenience seemed to be the only way to get through to him. Otherwise I would’ve been perpetuating the same situation.

  11. 31

    She’s had a crush on him for 20 yrs., but he may not have a clue as to that. Why should he if she’s always treated him as a friend? I think having a friend suddenly cut you off for no reason you are aware of is a pretty low thing to do. Some friend.

  12. 32

    I have a question that hasn’t been addressed so far. She says he is a good friend — has been a good friend for over 20 years. From what I can tell, the friendship has been mutually supportive — it doesn’t appear that he is just using her. So, just because he doesn’t want to add a sexual component to the relationship, why should she give it all up. Just as good romantic partners are hard to come by, so too are really good friends.

    There have been men in my life that are really good friends and for a minute, I thought I wanted something more, but I got over it. The fact is good friends typically last a whole lot longer than boyfriends. And I really, really value my friendships with men. So, I wonder why does it have to be all or nothing. Why can’t just continuing to be his friend while looking for a romantic partner be an option too. She’s done it before so it seems to me that she can do it again.

  13. 33

    Selena, if she feels more than just friendship for him, but he’s not reciprocating, then she needs to decide if she wants to continue this friendship the way it is. Of course, it wouls suck, but it sounds as if she’s having expectations for him that may not be valid.

    You even said, why should he have a clue if she’s always treated him as a friend?

  14. 34

    Kenley, you make some good points. Could it be that Maria wrote her letter to Evan in a moment of high emotion? Could it be that when the emotions have had a chance to subside, that she will think about this similar to those of us objective third parties?

  15. 35


    I think I understand your points in the main, and agree with them. If Maria’s “crush” feelings toward this man are keeping her stuck in some ways, she might well be better off sliding out of the friendship.

    However, we’re talking a friendship of 20 years here and there is nothing in the letter to indicate this guy has been stringing her along lo these many years just because he never asked her out. To abruptly end such a long friendship without any kind of explanation as to why… seems to me a bit cold. And rather cowardly.

    Seems to me you should be able to be honest with someone you’ve been friends with for 20 years. Otherwise what kind of a friendship do you really have? Rereading her letter, she mentions she has tried to cease contact with him several times to concentrate on another guy, but then he calls and rekindles emotions in her. So why not tell him this is what happens? If she’s serious about concentrating on someone besides him anyway.

    She also writes she’s “recently” divorced so there many be some other things going on with all this as well. Dunno.

  16. 36

    Good points, Selena. But I still think that if her feeling for this guy are holding her back, she should do something. It certainly won’t be easy because this guy has been a part of her life emotionally for some time, but we make choices in life. And if she wants things to change she’ll have to get out of her comfort zone.

    His calling her whenever she’s decied to move on was essentially testing her. Again, she has to evaluate what she wants and act accordingly, and only she would know the best way to handle this.

  17. 37

    Two options:
    1. Go out and get him drunk (and yourself while you’re at it) and seduce him using traditional chick methods of seduction. You know what they are so I don’t need to list them here. Wear a pushup bra.

    2. You could just ASK him to ask you out. Or ask him out first. If he says no or hems and haws, then you have your answer! Simple and efficient.

    See how easy that was?

    Lance´s last blog post…Thought Leader Interview Series: David Wygant

  18. 38


    I agree with you on that. I was just trying to be a bit more subtle when I said

    “Go up to the guy, whisper in his ear that you have always had a crush on him. Next drag your nose across his face so that barely rubs on the skin, then give him a peck on the lips, closed mouth. Get it done and over with.”

    I guess that you carried the idea to the next step

  19. 39

    I have been told/read about this very issue. If he hasn’t asked you out, there is a reason. He doesn’t want to. Unless you can crawl inside someone’s head, you don’t know what their motivations are exactly. He could be a little bit selfish and use her company to boost his ego when he is needing it. I bet he has a clue she ‘likes’ him and he may enjoy the attention. It’s not a real friendship anyway if she has to severe the friendship in order to move on with her life. Friendships between men and women just dont work when one has expectations or wants more and the other one doesn’t. 20 years? May be someone has intimacy issues herself and hasn’t faced them.

  20. 40

    I think that her friend is getting the raw end of the stick from some people. Why is he being selfish and feeding his ego because he enjoys her company? Why do we assume that he can read her mind and knows that she wants something more? Why isn’t it that he is content being her friend and he thinks she’s content being his friend too? Again, she didn’t say anything to indicate this man is selfish. Why do we always have to attribute such negative motivations men? Why can’t she be content just being his friend?

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