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Ask Dave: Gay & lesbian love

Ask Dave: Gay & lesbian love

By Dave Singleton Dear Dave,
I am a 20-year-old gay man and I can’t let go of my first love. We haven’t spoken or seen each other until quite recently when I added him to my MSN Messenger friends list. I see him online almost every day and keep track of him through his younger brother, who’s a friend of my brother. It kills me that I cannot be with him and it kills me that I can't confront him with how I feel.

Our history is that we dated for a long time, but I broke up with him due to trust issues. I doubted him a lot. We were very close and the feelings were mutual, but after breaking up with him, rejecting his apologies five times in a row and then calling him and hanging up, I’m afraid I really hurt him. I can’t confront him or talk to him. It’s just super-awkward, maybe because I hurt him way too much in the past. We live in the same town. I am in college and working. He’s unemployed and a high school dropout, which is a total turnoff for me — but not when it comes to him.

You see how confused I am? I don’t want to move on, but at the same time I’m dying to move on. Please help me find a way out of this misery. Do you think I should tell him exactly how I feel? Or should I avoid that?
-Dazed and Confused Dear Dazed,
It seems clear that your ex is on your mind because you have unresolved feelings for him and/or about the relationship. It doesn’t sound like you ever really had the breakup discussion to talk about why things didn’t work out.

As I see it, you have two choices at this point: Try to reach closure on your own or reach out to him. If you vote for self-induced closure, be prepared to forgive yourself and let go. Give yourself the understanding that a friend would give you. Remember, you were younger when you met and dated, and all of us make mistakes in relationships. Since it’s been a long time since your breakup, I think the statute of limitations on your perceived romantic misdemeanors has run out.

Adding your ex to your MSN Messenger — and now seeing him regularly on your computer screen — was your choice. That constant reminder of unfinished business is understandably frustrating. But my guess is that you want to reach out to your ex — and I think that could be healthy as long as you keep your expectations in check.

To paraphrase Glinda the Good Witch from The Wizard of Oz, you’ve always had the power to change this situation. In other words, you have more choices than you realize. Since you made the rule that you can’t confront or talk with him, you are allowed to change the rule. I am not sure that clicking your heels three times will work as it did for Dorothy, but confronting the situation now will.

First, understand and acknowledge the motivations involved with your wanting to reconnect. Yes, your current feelings towards this person are part of the equation. But look at other factors. He was, after all, your first love. I think all first loves should come with a warning label saying, Handle with Care: Getting Over This Will Be Difficult. Are you holding onto feelings for him? If so, these could be contributing to your inability to move ahead.

I suggest writing him a letter or an email rather than calling or IM’ing. In addition to catching him off guard, the latter two approaches might be painful for you if he lets you have it. With a well-worded letter or email, you can formulate exactly what you want to say. Here are suggested ideas for what to say:
  • Apologize for your behavior. Without dredging up all the dirty details, acknowledge that you were younger and now regret how you treated him.


  • Avoid blaming him and don’t be too hard on yourself.


  • Tell him that the goal of reconnecting is to apologize and clear the air. This process is not about possibly reuniting — or, at least, certainly not at this stage — but about repairing the way your communication ended.


  • Mention that, since you live in the same town and know the same people, chances are that you’ll run into each other one day. You’d like for that reunion to be as easy for both of you as possible.


  • Let him know that you’d welcome a response, but that one is not required. Make it clear that you respect his decision either to get in touch with you or not.
Remember, you never know how he might react. Maybe he feels badly about how things ended, too. You might talk about the breakup and learn and grow from the experience. Hopefully, you’ll clear the air. But there’s a chance he’ll consider your contacting him an intrusion. If he feels like you treated him badly, he might be holding a grudge.

The bottom line: It’s important to get closure on this chapter of your life. Whether you contact your ex or not, or if he forgives you or holds a grudge, you need to forgive yourself for what transpired. It would be a bonus if he, too, wanted peace between you. But you can’t count on it. Don’t waste any more time carrying the baggage of this former relationship. All you can do is say your piece. I hope you’ll get peace from that.



Dave Singleton, a columnist for Match.com since 2003, is the author of The MANdates: 25 Real Rules for Successful Gay Dating and Behind Every Great Woman is a Fabulous Gay Man (Advice from a Guy Who Gives it to You Straight).Please send your advice questions to AskDave@match.com or contact him at www.davesingleton.com.>