Dear Wendy
Dear Wendy

“How Can I Ask for a Second Chance?”

About a year ago, I was on one of those matchmaking websites and was contacted about a potential match. It took a number of weeks before I made contact with the guy in question (the company had to meet me and ask me a bunch of questions before giving him my number). I had to submit a ton of criteria for what I was looking for and they waited until they were sure he matched everything before introducing us. The only downside was he lived in another city but was contemplating re-locating to my area.

Anyway, he called me once or twice but a really long time went by between his calls (3-4 weeks) and things started getting serious with someone I was seeing locally. The next time he called and told me he was coming to my city and asked if we could meet for a drink, I told him, very politely, that I now had a boyfriend but wished him well. I even offered to meet as friends but he (understandably) wasn’t interested.

So, recently this boyfriend and I broke up. I’m wondering if there’s any non-awkward way to reach out to this guy and maybe even meet if he’s living in my area now. Clearly, there are a million things that could have happened – maybe he’s married or dating someone now, but I’ve got nothing to lose, especially if I kept it low-key and friendly (and not creepy). But I figured I’d get your advice. Would it be weird if I reached out? And if not, what should I say? — Second Chance

With the popularity of online dating, I doubt your situation is all that unusual. People make connections with each other, but for whatever reason decide to pursue one person exclusively and have to bid the other suitors farewell. Hell, even people who don’t do online dating are faced with similar decisions all the time. So, what do you do if it seems you didn’t choose the right person? If, weeks, months or even years down the road, you realize you and your significant other aren’t working out and you’re curious about whether things might have worked out with someone else you could have chosen instead?

If it were I, and I were definitely over the initial person I pursued a relationship with, I’d reach out to the guy I was curious about and say, “Hey, things didn’t work out in my last relationship and since I remember you so fondly, I thought I’d see if we happen to both be single at the same time again and if you’d have any interest in grabbing some lunch (/coffee/drinks/dinner) some time.” What’s the worst that will happen? You could get ignored or even told off, I suppose. If it’s the former, who cares? And if it’s the latter, then at least you’ll know you dodged a bullet.

Readers, have you ever been in this position? How did you handle it?

*If you have a relationship/dating question I can help answer, send me your letters at [email protected] and be sure to follow me on Twitter.

21 comments… add one
  • Budj

    Budj March 27, 2012, 9:30 am

    Never been in that situation, but I definitely agree with what you said. This is probably the best situation to “re-kindle” something (imo) because things never really got off the ground in the first place, but you know there is a good chance for a connection – as long as he is still single!

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  • Jess

    Jess of CGW March 27, 2012, 9:43 am

    Oh yeah, I say go for it. There is really nothing too lose. There is nothing creepy about reaching back out. If anything, it is flattering –even if he’s no longer single.

    By the way, it sounds like one of those elite/millionaire matchmaking services. I was once recruited by one and went through the long vetting process. It was a weird concept but I’d be lying if I said it wasn’t an ego stroke. I never ended up meeting one of their clients though –something always interfered on their end or mine. They still check in with me from time to time even though I’ve been in a relationship for awhile now. In the end, I found a man with a very humble paycheck and I wouldn’t change a single thing.

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  • avatar

    TECH March 27, 2012, 9:43 am

    I agree with Wendy. If you still have his cell phone number or email, it won’t hurt to send him a quick message. Nothing ventured nothing gained! What do you have to lose?

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  • avatar

    SweetPea March 27, 2012, 9:55 am

    The guy will probably be flattered that you thought of him after a year! As long as you were sweet to him when you turned him down, I don’t see an issue. And if he has a negative reaction, you didn’t lose much.

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  • dandywarhol

    dandywarhol March 27, 2012, 10:10 am

    Actually I have been through this, my current boyfriend and I got back together in a similar situation. We met 2 years ago, hung out for a few weeks, then he went back to Arizona (I was at school in Wisconsin at the time). Long story short, He broke it off because of long distance but then last year wound up back home. We started talking again, but i had a boyfriend at the time so nothing came of it for a while. Eventually though, that relationship ended and now I am with the first guy, after 2 years of not really talking. We just have this crazy connections I’ve never had with anyone. It sounds a little crazy but honestly…you have nothing to lose. I was actually floored when he texted me, he apologized for how it ended, and said he still thought of me. Your guy might feel the same, like “wow she still thinks of me? Awesome!” or he might blow you off. But you won’t know until you try. 🙂

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  • avatar

    java82 March 27, 2012, 10:22 am

    I’m totally in a similar boat right now: a guy I had been chatting with a year and a half ago, with whom I’d been texting and planning to meet for a coffee. He backed out 2 or 3 times due to work, but then disappeared. I thought he pulled the fade-out. Cut to two weeks ago, he actually saw me on another dating site and wrote that he “had to e-mail” me just to apologize, as we were getting along quite a bit back then. He even called himself an “apologetic asshole”, and asked how I was doing. I answered back, saying that I was bummed he had disappeared, but truly appreciated that he reached out. But he then never answered back. Grrr.

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    • landygirl

      landygirl March 27, 2012, 10:45 am

      He’s a flakey flick, don’t bother with that one.

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      • dandywarhol

        dandywarhol March 27, 2012, 11:30 am

        Agreed!

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    • Jess

      Jess of CGW March 27, 2012, 1:18 pm

      It think it’s the “back burner” game that many people play online because it seems like there are so many options. You want to keep a few people on ice in case the first one(s) falls through. Not cool for the person on the receiving end though. One or two flake-outs might be understandable but this guys has delivered the message that, for whatever reason, you (or dating in general) is not a priority. Move on, I’d say. You’ll only get more of the same (and worse) if you meet in person and start to date.

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  • Fabelle

    Fabelle March 27, 2012, 10:34 am

    Definitely go for it! If it seems awkward to be like, “Soooo…I’m single now!” I think it’d be okay to just let the fact that you’re initiating contact with him again speak for itself? (at least at this early stage)

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  • avatar

    jaybro March 27, 2012, 10:46 am

    As everyone else has been saying, go for it!! Just make sure that you’re completely over the old boyfriend before you jump in.

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  • avatar

    Ladybug March 27, 2012, 10:50 am

    I was on the other side of this situation with the guy I’m seeing now–we’d been matched online, emailed a couple of times, and then his personal life got crazy and he just dropped off the radar so to speak. I figured he’d met someone he was more interested in or just changed his mind, no big deal at that stage. I met, dated, and broke up with someone else in the meantime, and then got a message from this former online match out of the blue right after Christmas. He apologized for disappearing before, told me he’d never lost interest, and after a few more chat sessions asked me if I’d like to meet for dinner. It was flattering to know I’d managed to make enough of an impression that he’d want to pursue something over a year later, and as he had piqued my interest initially I saw no reason not to jump at a second chance. If I were in your position, I’d take Wendy’s advice and just casually reach out–you might find out he’s in a relationship or just not interested any more, but you could also find out that this is a relationship with real potential. I’d say it’s worth the risk.

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  • avatar

    AndreaMarie March 27, 2012, 11:20 am

    I met my current BF through a matchmaking service (SelectiveSearch)!

    I say go for it. Don’t start off with the “Things didn’t work out with my boyfriend so now I’m out looking again”. Just casually reach out. say you were going through your contact and came across is number and remembered all the good conversation you guys had..bla bla. Wondering if he’s in your city anytime soon and finally want to get together. Let him draw the conclusion (or ask you directly) about your relationship status.

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  • Moneypenny

    Moneypenny March 27, 2012, 12:18 pm

    I agree, go for it! You have nothing to lose, really. If he declines, you will probably never see him or hear from him, so what do you have to lose? Timing is super important, whether we like it or not, and this could be one of those instances where timing was not good with this guy last year, but there is the possibility that it will be in synch this time around. You never know! Good luck!!

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  • avatar

    Francine March 27, 2012, 1:17 pm

    Absolutely give it a shot! The timing wasn’t right before but there’s no reason not to give it a shot now. Nothing ventured nothing gained.

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  • avatar

    LizInVA March 27, 2012, 1:20 pm

    I agree with everyone else who has said “go for it!” I’m getting married this weekend to a wonderful man that I met through match.com. At the time, I had just broken up with a boyfriend and moved back to my hometown for a new job, so I really wasn’t ready for a serious relationship; so after several dates, I sent him a nice email saying as much. He was really great about it, wished me well, and that was that. Months passed and I got to thinking about him again, and finally got my courage up and sent him a really casual email. I even made up a story about seeing a new book by an author he’d told me he enjoyed reading:) I had no clue WHAT to expect but he emailed me back…he was out of the country on business at the time but we continued emailing until he got home, met for dinner, and picked up where we left off. It took my mom and a good friend to encourage me to do it, but I am so thankful I got back in touch with him. Timing IS everything, and you just never know what might come of it.

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    • avatar

      evanscr05 March 27, 2012, 1:47 pm

      Congrats!!!!

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    • avatar

      ErikaBrooke March 27, 2012, 2:13 pm

      I agree with Liz, timing is everything. I had almost the exact thing happen to me a few years ago. I met a guy online, and we talked a few times, but never ended up actually meeting because I started exclusively dating someone else. 8 months later I was newly single and I reached out to him, but he was in another relationship. But then about few months later he broke up with the girl he had been seeing and reached out to me. It was nearly a year after our first contact before we finally met in person, but we dated for two years and got married last May.

      I don’t think this situation is uncommon with online dating. And I don’t think reaching out to him again will be awkward if you keep it light and friendly. I say go for it! Even if he isn’t available now, he may be in the right place later on.

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  • avatar

    GertietheDino March 27, 2012, 2:13 pm

    The worst he can say is no, go for it!

    Actually the worst he could say is no…you heartless bitch, you toyed with my soul and I have never recovered.

    But still, go for it!

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  • avatar

    sarita_f March 27, 2012, 3:45 pm

    Another voice to the GO FOR IT. I was in a similar situation, and ended up dating the guy for 6 months.

    4 months in, turned out he kicks puppies and may have a diagnosable condition that makes him incapabable of empathy, but those first few months were fun!

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  • bittergaymark

    bittergaymark March 27, 2012, 11:19 pm

    You really have nothing to lose here, so I say, go for it. He may have moved on, sure. He may be in a relationship now. But so what? Then he politely declines just as you did. No harm. No foul. And who knows, maybe things could work out well this time…

    Actually, it would make for HILARIOUSLY bad Drew Barrymore movie if he was now in a relationship. But then later contacted you in, say, a few months only to find you mired in yet another relationship. Of course this cycle would go on endlessly in the flick until you FINALLY were both single — and cue the happy montage music — and you meet and live happily ever after together… Forever… The flick would costar Bradley Cooper of course and be called BAD TIMING….

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