Fail to Fab: Why Did Your Last Relationship End?

By Jess Downey, Copy Cutie

credit: woodleywonderworks (Flickr)As a singleton, I’ve had my fair share of experiences with getting to know someone new. And all too often I’m asked certain things about my dating past time and time again. Because it’s easy to perceive those inquiries as foe rather than friend, here’s a special Fail to Fab series on how to prepare yourself should these common crop of questions come up.

Fail: It wasn't technically my last relationship, but my last substantial something ended because the guy I was dating was picked up on the Manhattan Bridge and thrown into the psych ward at Bellevue (seriously). To say it's uncomfortable to talk about is a total understatement. In fact, this very subject came up on a date a little while ago. I wanted to hide under the table when my date asked about my past, but instead, I answered honestly and tried to laugh it off in hopes of keeping things light and fun. My date seemed fine and laughed too. But then, he started to dig at my former flame and make snide comments about my poor choice in men (which, if you think about it, kind of include him).

Fab: While this might be seemingly harmless question, it can send a date from "I'm having a nice time," to "Someone please get me out of here!" in less than 60 seconds. 

If you're the asker, let your date take set the tone. It's OK to have a chuckle or two if your date is, but don't take that as an invitation to make jokes at the old flame's expense. Don't judge someone based on the mistakes the people in their past have made. Instead, pay attention to what he or she has learned from the experience. Keep in mind that since this person is on a date with you, they clearly have good taste in picking a mate (right?).

Breakups can be difficult to deal with and recounting events surrounding one can be hard — even if time has passed. There could be things your date isn't comfortable sharing with you yet, and that's fine. Your main focus should be on whether your date is holding onto something that could damper his or her potential with you.

If you're the askee, keep in mind that your date probably isn't trying to pass judgment on you. He or she is just curious and wants to see if there's baggage — a natural reaction when seeing someone new. So give as much information as you're comfortable with. Just be aware that some explanation might be needed (like in my case), so be prepared to answer a few questions. It's OK to have a little sense of humor about what happened, but avoid spreading gossip or ex-bashing.

Remember: Dating is all about getting to know someone new, which often means exploring cringe-worthy subjects. But instead of becoming defensive, answer as honestly as you comfortably can — after all, the right match won’t care what your answer is.