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.

Join our conversation (63 Comments).
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  1. 41

    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.

    I have a feeling such a situation would be too unbearable for a man to stay in. I think the last thing a person would do in such case would be to want to “stay friends”.

    However, talking about guys being clueless about who has a crush on them.
    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. That’s not a subtle signal of interest. If anything less than a signal on this frequency is too weak for a guy to catch, then it is probable that he might feel he was receiving unclear signals, but it doesn’t necessarily mean that she was sending mixed signals

  2. 42

    My dearest Cinnamon, please decode the last paragraph for us guys on this blog. What are you saying?

  3. 43

    @hunter post #42

    That last paragraph by Cinnamon in post #41 was crystal clear to me.
    Maybe there are some things you can’t learn by reading a PUA site?

  4. 44

    Thanks Steve!

    And I’ve just started to believe I must have some special talent for encrypting my messages and pictured myself in a career as a spy 😉

  5. 45

    Maybe, I misread something. First, you would think he would have asked her out if interested. But, why could she ask him out on a date. Otherwise, she will keep waiting for the date that may never come. If they are such good friends, it should be easy to communicate her true feelings and find where she stands with him.

  6. 46

    Steve, give me your interpretation of, “If anything less than a signal on this frequency is too weak for a guy to catch, then it is probable that he might feel he is receiving unclear signals…”

  7. 47

    Girl to go,,,,,, some men will persist, even,,,,,,,, when,, there is no body language. Some men operate on the pretext, that,,, a womans feeling change, with persistance. A woman may say “no” this moment, but, that, does not mean “no” forever.

  8. 48

    …Isn’t that called, “Chasing?”

  9. 49
    Karl R

    Hunter: (#47)
    If a man requires an overt physical signal like the one described by Thomas (#26) in order to recognize that a woman is interested in him, then it is probable that he has failed to receive any number of more subtle signals that she has sent him.

    If the man requires a kiss on the lips before he gets a clue, then it’s rather likely that eye contact, “mirroring”, and compliments won’t be considered “clear signals” by the man. In his mind, he hasn’t been receiving clear signals. Even though, in the lady’s mind, she’s been sending consistent signals to the man.

    I don’t know whether that’s the case for Maria’s friend, but it’s at least remotely possible.

  10. 50

    I think starting to ignore him is extreme, & maybe rude as well. First, “No contact” does not mean being a d**khead. It means not initiating contact, & being cool, calm, & cordial when & if he does. Not being mean, hateful, etc.

    it isn’t easy.We know.

  11. 51

    Karl, I agree with you.

    However, in every day life, I have to say, most men don’t get the overt physical signal from a woman, Thomas wrote about. The clues are subtle, where if a man doesn’t get them frequently,(the plain, average looking man doesn’t) he won’t see her.

  12. 52

    I appreciate and have read everyone’s great advice. Thank you. The man in my initial letter confessed to me recently that I was his fantasy lover. He also said that he views me like a sister. Go figure!! LOL And men will say that women give mixed messages!!! I have come to the conclusion, without ever “pushing the envelope,” that it is what it is. I no longer pick up the phone at 10 PM when he wants to talk. I miss laughing with him, (we have always been able to laugh at even the most horrific circumstances in each others lives.) He has been calling more, not less. Always, what are you doing? What are your plans for the weekend, and NEVER asking me out. I am dating, and busy. I feel better, more in control of my emotions because I don’t talk with him so much. Life is good, I have met a couple quality men online. No love connection yet, but at least I am now OPEN to it!!

  13. 53

    Good for you, Maria! Thanks for the update.

  14. 54

    Maria, I think this man is lonely, and just wants to talk for now.

  15. 56

    I think you already have your answer. If she can be “just friends” with him, that’s great. But if he hasn’t asked her out in 20 years of friendship, it’s just not going to happen.

    I’m speaking from experience on this. I had a college friend I was friends with for almost eight years, and I had feelings for him pretty much from the beginning. In all that time, he never asked me out. I thought we were meant to be, and I made excuses in my mind as to why he wouldn’t ask me out. I even moved to the same town he moved to, in part b/c I was convinced we were destined to be. I finally fessed up, and in face he already knew I liked him but he was totally not into me. I spent eight years being unavailable b/c of someone who wasn’t interested in being anything other than my friend (and he strung me along to boost his ego at that – he admitted such). In the end, we couldn’t even remain friends.

    It has been two years since I stopped being friends with this person, and releasing myself was the best decision I ever made. My current boyfriend of three months is a shy and reserved person, and yet he had no problem asking me out not long after we met.

    My point is that there is no excuse worth waiting years for. If he is interested, he would’ve asked her out by now. He hasn’t, so he’s not into her. That simple. She should focus her efforts elsewhere and stop wasting decades of her life.

  16. 57

    Hi Jaye, and wanted to give you all an update. The man in my initial letter phoned me this week and admitted to having a couple of drinks prior to calling me to muster courage. He said, “you know maria, we would be a great couple. Instead of talking on the phone all the time why don’t you just please come over to my home so we can spend some time together.” I didn’t know what to say. You have all helped me move on, and the moment I thought would never come, finally came -but my gut response was indifference. Women are accused of playing games, but truly I am not trying to. Once I moved on, I just moved on and I don’t think there is any going back. Right now I have a crush on someone else (which is probably going nowhere and will not last 20 years), and thats where I am. Timing is everything. As the world turns….

  17. 58

    Maria, sounds as if, it took him too long to respond, some men are slow…..

  18. 59

    I think I would take Evan’s well considered advice, and let it go. I’ve been there myself, so I speak out of understanding. I would not suggest asking him out. You’ve spent too many years building up your hopes, and you are likely to be shattered upon finding out that nothing was there.

    I had a crush on a man from age 17 to 32. I also made up excuses – he’s shy, he’s afraid of rejection, and so on. We didn’t really have any contact – it was more a case of seeing him at events and group outings. I felt firmly, and I still do today, that chasing him and asking him out would put me in a losing position. So I waited patiently for something to happen. The only thing I had to go on was he stared at me, and that he apparently twice asked my friends about me. Bottom line: he never did a thing.

    Two years ago, he turned 48 and married a 24 year old foreign woman who he sponsored her immigration over here.

    I can understand the rationalizations. I know that actually asking him out and having nothing come from it would have shattered me. I’m glad I didn’t expose myself to the humiliation. Much of my feelings were built up by illusions I had about him. By giving him up I would also be giving up my hopes and dreams, and face really nothing. It was difficult to give up on him.

    I now wish I hadn’t wasted my time with him. I did date men all those years and had several long term relationships, but always had him in the back of my mind. It turns out that it was a waste of my feelings and energies.

  19. 60

    I am wondering if he stared at your figure.

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