Fail to Fab: When Was Your Last Relationship?

By: Jess Downey, Copy Cutie

credit: DaveFayram (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: If there’s one question I absolutely despise, it’s anything that has to do with how long I’ve been single. Call me crazy, but telling a guy that you’ve been single since the Stone Age just doesn’t scream white picket fences and china patterns. So more often than not, I’m usually on the defense whenever this particular subject arises. And I found myself in this very situation when I was on a date a few weeks ago. The guy and I were having a light and fun conversation when he asked the question. I thought about my response, but ended up launching into a series of questions asking why he wanted to know and how he would define a relationship. Definitely one giant #fail.

Fab: A whole lot of this question depends on how it’s asked — and how it’s answered. If you’re the asker, be sure to choose a time that naturally fits with the conversation. If you suddenly drop the bomb in between your recent vacation to Italy and your trip to Lollapalooza, you’ll likely send your date into a frenzy. 

If you’re the askee, don’t fret — consider it a form of flattery. It actually shows that your date is interested in you as a potential future boy or girlfriend, so cool your nerves and show him or her you’re open to what can happen.

Avoid the verbal vomit with questions about who, what, where and why. Also, asking for someone’s definition of a relationship only makes you look wishy-washy. Be confident about where you’ve been and where you’re going.

If it’s been a while since you’ve had a sweetheart, it’s perfectly acceptable to say so. But be sure to keep things upbeat and give some sort of time frame of the last time you had something substantial. This is a question that’s bound to come up if you and someone become official anyway.

Regardless of your situation, keep in mind that your date isn’t trying to pass judgment based on how long you’ve been single. He or she probably just wants to see where your head (and heart) are at. Woo your date by reassuring him or her that you’re open to new possibilities.

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.