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. 61
    Peyton Place

    I understand you feel your story is unique, as you think the years make a difference. They do make a difference, but only to you. I recently found my first love, after 28 years, same type of situation, and he put me in the friend zone, but quick. He wanted to talk about the most mundane aspects of his life, daily calls, texts all the time, etc. But when he went away on business trips, he was only still talking about how to change the oil on the car or what happened at work that day, no more sexy conversations. The fun texts and calls went on for the first two months, then, nada. My male friends say he stopped because he did not feel it would progress to anything ever, so he figured, why spend time being flirty? I told him I was busy with work, blah blah, and he gave me the same story. He sent some lame texts after that, then, nothing. I got over him by reminding myself I did not want to be in a relationship by myself, which was what I was getting – and it felt like crumbs. Don’t give someone else the keys to your happiness again, be happy on your own and find someone else. If men “do what they want” then find out how to do what you want. Cut him loose. Sounds like an emotional booty call, and it is never a good feeling to be on the other end of it, I have been there many times/years. It is hard to get over a guy, trust me I know. Every time I said to myself, “But if he would only…” I made a point to “punish” myself with something that was good for me, like walking further on my daily walk, beginning a daily walk in the first darned place, or eating a healthier choice on my diet. Go get a spa day, try to get over this guy, your heart is not open for someone who will bring you to a better place, but that guy could be looking at you right now, so shape up quick and change your attitude, girl!

  2. 62

    I know that I posted a reply on here before I went and looked at all of the replies to the post that was written. I fell asleep as I was reading them and watching TV. However, no matter how old a story is, along with it’s replies, people come here and still read this stuff if they are going through the same, or close to the same situation as the person who had written about her friend that she likes. I wanted to say a few other things that I failed to mention in my previous reply. I can be a little old fashioned when it comes to the woman asking the man out. Especially these days where it seems like ANYTHING goes. Practically everything that was once not considered to be okay is now acceptable to a lot of people. I do not agree with it either. However, like I had mentioned earlier… I think that it is okay in certain situations. I asked one man out before. I am not a young person either (mid 40’s). Anyhow, this man was a friend of mine too but we were not as close at all as you and your friend are. However, I just knew how this particular friend of mine was and we have quite an age gap between us too. Therefore, I knew that he would not ask me out even if he wanted to. I just really liked him and he made me feel so happy whenever I was around him. Good sense of humor, we had a lot of the same interests and he was a genuinely FUN person to be around too.   I love a man who can make me laugh and he could definitely do it without even trying. I finally got up the courage to call him one evening and talked to him for a few minutes and then I just asked him if he would like to go out with me. There was a very lengthy pause after I had asked. I just knew that he would going to say no at that point. He then said “Well, Uhm… YESSSSS”! There you have it. Sometimes the men are just as frightened as you are too. As I will say over and over again though… Use this lightly and according to the situation. If it were me and I had a friend as long as you have and had a crush on him for such a long length of time, I would likely ask. However, I have a pretty good judge of character when it comes to this type of stuff too. I would have to see how you and your friend actually interacted on a daily basis to decide if I would ask him out if I were you, of course. You really never know until you ask, if you feel that you need to find out because you feel that your friend and everything about him feels so right. However, be prepared for anything when he answers. From the way that it did sound from this post and what I read though. I   would have thought that your friend wouldn’t have had any issues with asking you out after all of this time as close as the two of you seem to be. That is just my opinion though.   If both people have that attraction, it just comes out sooner or later. It is only normal and will happen naturally.   I will get off of here and read more posts now you all. Sorry for the lengthy replies. I just know how bad that it feels when you like someone that much and you have no idea whether or not they like you back. It is very tough. Thank you to everyone who read this reply/novel. I wish everyone out there the best of luck. Everyone deserves to be loved and find that special person in life that they belong with for the long haul.

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