Ask Dave-I turned him down

He was otherwise involved and emailed a “no thanks”…but wants to reconsider. How can he do so?

By Dave Singleton

ear Dave,
I’m a 37-year-old gay man who’s been dating online for two years. I seem to go through periods of feast or famine. Sometimes, there are several guys who spark my interest and I’m dating around. Other times, it’s quieter.

Several months ago, I went through one of those “feast” periods and met two guys I liked, one of whom I dated for three months (I’ll call him guy
I’m considering recontacting guy #2 to see if he’s interested.
#1). I met guy #1 a few weeks before guy #2, so we had a head start. After three dates with guy #2, I told him I wanted to pursue dating guy #1 and didn’t think I could date two guys at once, especially since all of us claimed to want a real relationship. Guy #2 made it clear he was disappointed, but took the news pretty well.

The relationship with guy #1 didn’t work out. I’m considering recontacting guy #2 to see if he’s interested. Is that weird? Any tips for how to approach him without sounding like I’m desperate or reminding him that I didn’t pick him first? He’s a great guy. The timing was off. Should I try again?
– A Case of Bad Timing

Dear Timing,
If bad timing is all it was, then by all means try again. Will it be successful? Who knows? Guy #2 might have met his Mr. Right by now. It’s doubtful he’s been sitting on the online-dating fence quietly waiting for your return. But if he’s still single, then your approach to guy #2 will probably determine how receptive he’ll be to the idea of dating you again.

First and most importantly, convince guy #2 that you’d like him to be #1 now. Before you do that, make sure that you’re recontacting him for the right reasons, which include romantic attraction and a genuine interest in him. It counts in your favor that you were upfront before romance got too heated. He’ll probably respect that, especially if you indicate that your “one-man man” approach will apply to him, too.

So how do you make sure you’re reaching out to him again for the right reasons? Ask yourself the following questions, and consider these tips for reconnecting:

1. Were there any issues when you dated guy #2?
Are they still concerns? If you reconnect and start dating him again, what would be different?
Tip: Dating is a process of discovery. Honestly reexamine why you didn’t choose to pursue dating guy #2. Search out answers to any lingering questions you might have, based on what you know about him.

2. Are your reasons for reconnecting sound?
Or are you just missing the attention and on the rebound?
Tip: Reuniting out of fear, loneliness, or a desire to rebound is never a good idea. “When you date on the rebound, there is a strong risk, unless you are extremely self-aware, of hurting yourself and others,” says Lorna MacKinnon, author of Cosmic Coaching.

3. Are you planning to date him exclusively or continue dating around?
What are your expectations for
Technically, you did nothing wrong.
Tip: If guy #2 moves into the #1 position, then your dating reentry point, so to speak, is a little further along than if you just met him. Of course, you can agree to revisit romance slowly. But be prepared to clarify expectations immediately with him. You can make it clear you’d like to try again and that you are aware it might be hard to pick up where you left off.

4. What will be different this time around? Are you in the same place, wanting the same level of dating?

Tip: Only time and talking will tell. Even if he’s interested in reconnecting, expect some initial trepidation. Technically, you did nothing wrong. You were upfront before romance got too heated and left him to pursue someone else you’d met weeks before. Still, there could be some small traces of abandonment feelings that he’ll be able to work through with a little TLC.

Bottom line: The best thing you can do to reconnect with guy #2 is be honest and respectful. Get him to see that a case of bad timing then doesn’t preclude healthy dating now. The worst thing you can do is anything that fans the flame of desperation, yours or his. By showing your potentially rekindled date careful consideration, you’ll show him that you’re worthy of a second chance.

Dave Singleton, an award-winning writer and columnist for since 2003, is the author of two books on dating and relationships. Send your dating questions and comments to him at
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