By: Jess Downey, Copy Cutie
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: As a gal who’s been single for the better part of the past decade, I don’t always feel comfortable sharing my dating past when I’m chatting with someone new. And I found myself in this very situation about a year ago. I was having a swell time on a date with a guy when he asked why I was still single. Almost immediately, my mood changed from flirty to frantic, and I launched into the why-do-you-want-to-know-a-thing-like-that? spiel. My date was embarrassed and for what seemed like hours, we fumbled around, trying to find our way back into the conversation groove.
Needless to say I never saw that guy again. While I can’t say for sure it was due to my freakish behavior, it surely didn’t help woo him.
Fab: Be sure to keep your cool around this question; otherwise you’ll come across as either the jaded hater of the opposite sex, or the casual dater who’s only interested in flying solo. And clearly, neither persona is good for your dating life.
Before you answer, keep in mind that a question about your single status can be purely rhetorical or meant as a compliment. Before you think here we go again and jump to the defense, try to read your date.
If it’s truly a question, remind yourself that there’s nothing wrong with asking why. Your date might not be looking to make a judgment, but genuinely curious to learn more about you. After all, that’s part of the get-to-know-each-other process. So instead of questioning them, give an answer that you’re comfortable with.
While you don’t have to share things that make you squeamish on the first date, you don’t want to hide things, either. We all have a dating past so be confident about yours — find a middle ground and rock it.
Regardless of your answer, things might get a little awkward. If your date seems unsure of what to say next, don’t assume you have to go on with excuses about your reasoning. Instead, take the lead by transitioning to another topic to keep the conversation flowing.
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.