Fail to Fab: How Long Was Your Last Relationship?

By: Jess Downey, Copy Cutie

credit: danja. (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: Not too long ago, I was on a third date with a guy. Like our previous encounters, things were off to a great start. He was very charming, and I’ll admit I was swooning (a little) about the good vibes. We were at dinner and had just ordered another bottle of wine when he said, “So tell me how long your last relationship was.” As a gal who hasn’t had anything substantial in quite some time, I wanted to hide under the table. Instead, I was honest and answered “Under a month.” My date followed up with a series of questions that mostly stemmed around his assumptions that I’m a casual dater — and a flight risk. And every time I would try to explain, he’d cut me off with some sort of Judgy McJudgerson comment. #Frustrating

Needless to say, that was our final date. While I think it was for the best, I do wish my dating past hadn’t been the demise of what might have been.

Fab: This question has dating failure written all over it.

If you're the askee, try not to get too tripped up on how you think your date is expecting you to answer. There’s this idea that if you’re of a certain age, you should have a heap of amazing long-term relationships in your back pocket. Either way, you are who you are (dating past and all), so rock it.

While it’s true that your answer might raise a couple of red flags, keep in mind that it doesn’t necessarily mean he or she won’t date you. Don’t be afraid to answer questions that will explain your situation and put your potential boo’s mind at ease.

If you're the asker, try not to judge someone based on the answer alone. He or she might have a perfectly good explanation as to why there's only been a few casual affairs as of late. Furthermore, some of those reasons might be totally beyond this person's control. Also keep in mind that being a habitual relationship person doesn't necessarily make them a prime candidate for love, either. What's really important is his or her reasoning and what he or she learned from experience. Be sure to ask questions that help you see the whole picture.

And if you find that there are too many red flags for you, it’s perfectly acceptable to go your separate ways. Just be sure to bow out gracefully.

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.