How To Answer Awkward Questions About Your Dating History

How do you answer the question “so how are you still single or why are you single” to men on dating apps? I have past trauma and I’m 37 with no kids and never married. Last long term relationship was many years ago. It’s embarrassing when men consider me a “catch” but also a red flag. I don’t know how to answer the question without being extremely embarrassed. I feel like men think I’m crazy because I’ve been single for so long.

This question came up in last night’s Write The Best Dating Profile Ever Workshop. (Next one is June 26th at 4pm Eastern.)

As I said to the person who posed the question, a several year gap between relationships is not in any way atypical these days. In facts, it’s fast becoming the norm. Dating in the age of technology is no walk in the park. Anybody who’s been trying to navigate the dating landscape in the last ten years can attest to this.

I just published my DateSpeak E-guide and address this and many other awkward personal questions people ask and get asked. From the e-guide:

To be very clear: This is nobody's business. You are not obligated to answer this question. You can if you want, but I advise not to. Once you answer one personal question from a stranger, it's almost assured they'll start asking others. The reason this question is problematic is because, without context, the answer is meaningless. To get context you'll need to ask a series of follow-up questions. Now your initial conversation or first date has turned into an inquisition.

If someone asks this question before they properly get to know you, like on the first or second date, don’t ask them to qualify what they mean by “relationship.” That way your answer can include anything - a brief fling, a situationship, what have you. It’s bad enough they’re asking this question at all. They don’t get to play the semantics card.

If you want to be direct you can say your last relationship was a few years ago. If they ask why just tell them dating hasn’t been a priority for you until now.

If they ask you why you’re still single, they’re tipping their hand to their own social awkwardness. They’re revealing their suspicious nature without realizing it. All you have to say when asked why you’re single is, “Huh. I don’t know. I’ve never really thought about it.”

You are not a red flag. The red flag is someone who thinks it’s appropriate to pose personal questions to a stranger they’ve just met. I understand why some people think this is an appropriate question and why they would want to optimize their time, but your letter is a perfect example of how triggering this question could be.

A lot of people experienced trauma in their formative years or previous relationships. I’m one of them. I’m also a great partner due largely in part to that aforementioned trauma. It made me compassionate, attuned and self-aware. Those are some outstanding qualities. You probably possess similar ones.

Someone who dismisses a potential match for not having what they consider a sufficient amount of relationship experience without knowing someone’s back story is just ignorant. I also suspect they ask these questions hoping to uncover something “problematic” so they can reject someone.

The real bottom line is this: If they’re interested, your answer to this question will not matter. It might give them pause but they will still continue to get to know you.