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 firstname.lastname@example.org and be sure to follow me on Twitter.