I Have Been Holding Out for My Crush for Over 20 Years

In 8th grade I developed my first crush. She was all I could think about but I was too scared to ever talk to her. I was thinking and hoping it would be easier in high school. It wasn’t. There were attractive girls and some even expressed interest in me, however I was not interested in any of them as I still could only think of my crush.

Sophomore year of high school I developed a new crush. Another girl I could not stop thinking about. It lasted about one and a half years and once again I could not talk to her. If she tried to talk to me, I was practically paralyzed.

If figured maybe college would be better. I was approached by some women, but once again I was not interested in any of them.

In the meantime, I still was still too scared to reach out to my crush and was hoping to maybe run into her somewhere somehow, even though I knew almost nothing about her or how to find her. However, I never felt similarly about anybody else.

I did go to bars or parties but was never interested in anyone to ask them out.

I did go on some dates, usually some suggestions from friends of family, but once again they went nowhere as I had no interest in any of them.

A little under 10 years after high school, a friend did try calling her, but it was too late and she was getting married.

I have tried dating sites like Match and eHarmony and even apps like Tinder, but it never goes anywhere as I don’t feel anything and physical attraction is not enough for me and never was.

Ready for Lasting Love?
Ready for Lasting Love?

It has been over 20 years since high school. I have never seen or had any contact with my crush. I still go on dates and do as many different things as I can, but I have no interest in anyone else. If anything, I recently started thinking more about her than before.

So how can I get over her and finally develop a feeling for someone else?


Michael, thanks for recounting your painful story. It takes a lot of courage to put yourself out there like that and I appreciate you walking me through your history.

This is the part where I’m going to remind you that I’m a dating coach who happens to have a blog.

This is the part where I’m going to remind you that I’m a dating coach who happens to have a blog. Although I’ve doing this for 16 years, I’m not a licensed therapist and don’t even pretend to be one on TV. After answering probably 600 questions on this site, I sometimes feel like I’ve seen it all, but letters like yours remind me that I haven’t – and I’m really not qualified to tell you what to do next, besides “get a licensed therapist.”

That doesn’t mean I don’t have an opinion; it just means that what you’ve described is extreme behavior and falls outside the realm of “normal” problems I tend to help clients navigate on their journey to creating healthy long-term relationships.

Your situation is, well, different.

You seem to have turned your 8th grade crush into a fantasy and anchored so closely to the fantasy that you’ve made it into your thirties without ever having a love life.

I can only imagine how hard that is on you – and can only imagine how deeply you must feel about this woman for you to forgo all other possibilities for two decades.

But here’s the thing, Michael: fantasy is not reality.

The woman you have a crush on is now married.

Even if she wasn’t married, the idea that she’d respond to a stranger who was lurking in waiting for twenty years is virtually unthinkable.

You think you have feelings for her but whatever you’re feeling, they’re not feelings for HER since you don’t actually know her. She is, quite literally, a fantasy of your own making. Whatever qualities you think she possesses (apart from physical ones) are almost exclusively drawn from your imagination.

I know that may be hard to take, but it’s true. What further complicates things is that you’ve had so little experience with other women (because you’ve been holding out for your crush) that you don’t even have an inkling of what other women are actually like.


It’s like you saw an ice cream cone when you were 13, never tasted it, but decided to go on a hunger strike until you ran into that same exact ice cream cone. No wonder you’re malnourished. You have unintentionally sidelined yourself from developing your taste in women while everyone else was busy getting real-life experience with real-life people.

And that’s the biggest flaw in your plan, Michael: there are a bunch of things that seem to have never occurred to you. Like, is she a nice person? Or, is she emotionally healthy and a good communicator? Or, does she practice the same religion or want to have children? Or, do you enjoy her personality and sense of humor? Even if you’re aligned on all of these things, the other thing that never seemed to break your spell was that, in all likelihood, she wasn’t going to like you back – not in the short-term and not in the long-term.

Hate to break it to you, but it’s true.

The shy stalker never actually gets the girl of his dreams.

So while you’ve tortured yourself these many years, waiting for some new woman to tantalize you out of your eighth-grade stupor, what you were actually doing is playing it safe. By not giving a chance to other women, you get to believe your built-in excuse that “nobody else is attractive,” or “I’m not interested in anybody else,” when, in fact, there are tons of attractive women out there, if you actually gave them a shot. Alas, not giving anyone a chance is your safe zone. Your logic – to you – is unassailable. Who can argue with a man who has such high standards for female company?

I can.

I have sympathy for you, my friend, but not so much that I’m going to let you off the hook for your predicament. You’ve avoided rejection for the past twenty years by never showing interest in anybody – primarily because they can’t compare to your fantasy cipher who you don’t really know. It’s time to drop that story.

You wasted two decades of your life.

Don’t waste any more.

Go out with a woman – any woman – with an open mind and forget your crush ever existed.

I promise: she’s already forgotten that you did.