Fail to Fab: Have You Ever Been In Love?

By Jess Downey, Copy Cutie

credit: kewl (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: A few years ago I was on a first date with a guy I had recently met. We were making the usual conversation when he asked, "So — have you ever been in love before?" While I was a little thrown by the question, I had nothing to hide and answered truthfully: "Yes, I thought I was, but it ended kind of badly." While the situation was more "tragic" than "bad," I downplayed the situation in hopes that my date would move on to a new subject. Instead, he followed up with a list of questions. And before I knew it, more than an hour had passed and I had pretty much told him the entire (tragic) story. Talk about a total mood killer.

Fab: This question is best asked when you’re ready to have the conversation; a simple yes or no won’t do much. It's pretty difficult to formulate opinions about someone’s relationship past without asking other things. No matter what side of the ask you’re on, questions are perfectly fine. But keep in mind that telling the story from beginning to end could make your date squeamish … or open up old wounds. Be open for dialog, but don't push the limits.

Love stuff is a pretty heavy and serious subject so it's best to leave it for date four — or beyond. That way you have a better understanding of the who, what, where, and why of the relationship. When you decide to chat about it, remember that you're still on a date. Keep things light, and be sure that the topic flows into the conversation naturally. Abruptly throwing it in after talks of what's on your bucket list isn't likely to woo your date. And if you feel the conversation is getting too somber or intense, ease into another subject. 

There's this idea that if you're a certain age you should have some sort of significant relationship under your belt. But whether you're the askee or asker, keep in mind that significance doesn't necessarily equal being in love. So if you haven't quite been there, that's OK! Instead, share details about a time when you really cared for someone — it’s still a meaningful relationship.

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.