Posing This Simple Question to a First Date Will Doom Your Chances of a Second Date

January 18, 2018

I just read this article in Business Insider the other day called “Posing this simple question to a first date will help you decide if you have a future together.” As a dating coach who gives plenty of first-date advice, I was obviously curious to see what this “simple question” could be. I tell my clients to start a date with “How was your day?” to get the ball rolling and show that they want to hear what the other person has to say. Or, maybe it was going to be “What’s your ideal Sunday morning?” to see if you have similar lifestyle habits. Sadly, it was not. It was instead, “So how come someone as wonderful as you is still single?” I was appalled.

To start, this question is a back-handed compliment at its finest, with undertones of “What’s wrong with you?” or “Why does no one else want you?” This question immediately puts the person at the receiving end on the defensive, when that person has nothing at all to be defensive about. At best, the person can deflect this question by saying something like, “Aren’t you lucky that I am?” or “So I could meet people like you!” But this is just a way to move past the uncomfortable part. Remember that being single is not a crime. In fact, it’s a valid life choice that many people desire.

What is most bothersome is the word “still” here, as if one thinks you’ve been single since the day you came out of the womb. The reality is that we never know the other person’s story. Perhaps this person has been single for a month, after a breakup. Does that imply “still single”? Or, perhaps, god forbid, this person’s partner passed away. Does that imply “still single”? Or, maybe that person was taking some much-needed self-reflection time (which is too often overlooked) before dating again. Does that imply “still single”? Let’s dissociate the word “still” from “single” immediately. If someone is single and dating, then use the term “available,” not “still single.” Someone available can be an asset to you. Someone available connotes scarcity, that he or she won’t be available for long. Someone “still single” is deemed lagging or behind, and that is not the case at all.

Asking why someone is still single also implies that being in a relationship is the one and only best outcome for everyone. That’s simply not the case. I’d much rather be judged for being “still single” than in a relationship that doesn’t fulfill me or that makes me feel badly about myself. Yet, someone in people’s minds, relationship status overshadows single status every time. Let’s end that thinking.

When you go on a date, the focus should be on the present, not the past. For that reason, I discourage my clients from discussing past relationships on the first date. I want to make sure they have some rapport first before getting into the nitty gritty details of a divorce or break-up on a first date, or ever. Talking about prior relationships often brings up difficult feelings, usually negative, and takes the tone of the date down. Talk about things that make you happy, what you like to do, and who you are as a person… not who you used to be, and who you used to be with.

The author’s rationale is that someone will either hold him or herself accountable for the last relationship ending or not. That’s some deep stuff for a first date. I’d argue that you can learn just as much, if not more, about someone by asking “How was your day?” If someone goes into a tirade about his or her boss not being fair, that is very telling. Or, if someone is so excited because of a surprise Mexican food luncheon at work that day, that also gives us useful information.

So, do you want to know one surefire way to doom a first date? Ask “So how come someone as wonderful as you is still single?”