“I Let Go Too Easily!”

The Internet makes it easy to reconnect with friends and lovers past, but is it always a good idea?

By Dave Singleton

ave you ever wished you had fought a little harder to save a romantic relationship before you called it quits? Michael, 43, of Washington, D.C., has, and his Internet search history proves it.

“I admit that there’s one guy I search for every few months just to get updates and to see a picture of him
“It was over. But he’s definitely the one who got away.”
again. He was intellectually, emotionally, spiritually and physically ideal,” says Michael. “Professional challenges on my end, and a personal crisis on his, stopped the momentum of our relationship. It was over. But he’s definitely the one who got away.”

Does Your Past Include a Man That Got Away?
Many guys like Michael wish they’d tried harder to keep the flame burning. Now after years of being apart, Michael wants to call the man that got away and send a low-key “Hi, hope life is treating you well” message. Of course, he’s a little reticent. He doesn’t want to come across as a stalker. But hope for a second chance outweighs his lingering doubts.

Technology Makes It Easier to Reconnect
For those of you who want to, à la Cher, turn back time and try again with a past love, there’s good news. There are many ways to reestablish contact without putting your heart on the chopping block.

The days of sending an “I miss you, please come back” missive via pony express or showing up at your ex’s door years later are over. Thousands are reconnecting through Web-based communications and social networking sites. An email address found through an Internet search makes it easy — and less emotionally fraught — to send a feeler out to an old love.

Really, what have you got to lose? If you’re living in the glow of a past romance cut too short, why not email or call, like Michael plans to do? How about friending him on Facebook? That worked for Bill, 32, of New York.

Replace Regret with a Reignited Romance
“I missed my old boyfriend,” says Bill. “It’d been three years since I’d left abruptly and he moved on to someone else. When I heard he was single again, I sent him a Facebook friend request and we met for lunch. I apologized for walking away after a fight and he apologized for his part in that fight. Since we never dealt with our hurt
“Second-guessing my choices only compounds an already drama-dense dating scene.”
feelings nor addressed our breakup properly the first time, we got a second chance. Within weeks, my ex and I rekindled the romance and our ‘take two’ has been going strong for eight months. We’ve chalked up our first breakup to lessons learned.”

Bill’s story illustrates that you never know what an ex’s reaction may be one, three or 10 years later. Circumstances change. Partnerships end and people are free again. Grievances melt, giving you a chance for restarting a love gone on the rocks.

If You Strike Out Twice, Give Yourself Credit for Trying
Dan, 35, of Washington, D.C., wasn’t as lucky at love — or closure — the second time around, but he’s glad that he tried.

“My boyfriend of nine months and I broke up out of the blue. He never complained about anything, so there weren’t warning signs. I like to avoid conflict, so when he told me he wanted to stop seeing me, I sheepishly accepted it without trying to fight for the relationship. I guess I was afraid of finding out what bothered him. Who wants to hear a laundry list of your faults? Looking back, I wish I’d asked why he was unhappy; maybe then I could’ve tried to fix things. We had something special.”

Dan eventually got over his prideful reluctance and called to reconnect. “I left a message,” says Dan. “He never called back. At first, it really bothered me. But now I realize it was more his discomfort at addressing uncomfortable situations than anything else. I’ve made my peace with it.”

Confronting the Past Can Help You Release It
Often, the one that got away looms large in your memory. It’s easy to romanticize your missed Mr. Right, isn’t it? But as Chris, 32, of Austin, TX, learned, maybe the romance ended for a good reason that you can no longer remember.

When Chris finally called the “guy I’d come to think of as ‘the one I shut out,’” he wondered if he could relight a spark that he helped extinguish. “In my memory from years ago, he was perfect,” says Chris. “But once we were reunited, our old issues resurfaced. I’d forgotten how badly he treated me and how much I’d changed for the better. Reuniting helped me see how relationships that don’t work out help you grow so that you can be ready when the right one comes along.”

Of course, not everyone feels the need to try again. “I have no regrets,” says Michael, 35, of Washington, D.C. “They were cut — or I was cut — for a reason.” David, 45, of San Diego, agrees. “Second-guessing my choices only compounds an already drama-dense dating scene,” he says.

But if you’re holding tight to the memory of your guy who got away, why not reconnect? Limit the emotional risk by preparing for whatever his response might be. After all, you don’t know whether he’s single or partnered, the same guy you remember or someone different, or if he’s missing you just like you’re missing him.

All you know is that your memory of a premature love TKO makes you wish you hadn’t thrown in the towel. Even if reconnecting just leads to closure, it’s worth it.

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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