QUESTION: When I’m dating, I really struggle with how to answer questions about my (lack of) relationship history. Within a few dates, the question about past relationships inevitably comes up, and I never know how to answer this. I want to be honest, but as someone in my 30s with little relationship history, I know that isn’t the norm. I’ve had experiences where the tone of the date has changed after disclosing that I’ve been single for most of my life. A lot of men seem to see this as a red flag. Do you have any tips for how to handle this topic when it comes up on a date? – M
ANSWER: I always hated this question too. I had been relationship-free for about eight years before I met my husband, so when this question came up on dates I … hedged.
I know, I know! It shouldn’t have to be this way! In a perfect world, I would have simply offered up the hard numbers, and none of my dates would have blinked. In a perfect world, we would all recognize that the person who rushes to the nearest warm body after each breakup should not be considered more “qualified” for a relationship than the one who knows how to walk away from (or never start) something that isn’t working.
What can I say? I didn’t want to deal with all that baggage. I didn’t want to explain myself—at least not on the first or second date. And quite frankly, I didn’t want to immediately dive into a topic that was sensitive for me. So instead, I’d wryly say something like, “Oh, it’s been awhile,” and then make some kind of arched-eyebrow comment like, “but you know I’m enjoying life.” (A little gentle sarcasm can go a long way. It’s a way of saying, “I know we’re both too cool and smart to make each other justify our relationship resumes.” Who’s going to argue with that?)
Then I’d ask my date a question, any question. Sometimes it was marginally related to the topic (“What do you usually do on weekends?”). Sometimes it was in a completely different ballpark (“Have you ever eaten here before? What’s good? I’m thinking about the vodka penne.”)
In other words, I did a basic redirect—something you can watch politicians do nearly any night of the week if you flip on a cable news channel. (“Governor, why did you steal money from the teachers’ pension fund?” “That’s a great question, but you know the real issue people care about is jobs.”)
Hopefully, your dates won’t go all Anderson Cooper on you and demand an answer. If they do, that will tell you something. A crooked politician is duty-bound to answer journalistic questions. A person on a date is not. You don’t have to tell your date everything immediately. You’re allowed to avoid topics that are sensitive to you. You don’t have to divulge your deepest insecurities until that person proves worthy of your trust.
A conversation, especially one on a date, should be a dance, not an interrogation. You ask each other questions because you’re interested in getting to know each other. You delve into the topics that interest the two of you and leave aside the ones that don’t. For example, imagine you’ve just asked someone if they have any exciting travel plans coming up, and they say no, they’re sticking close to home because they’ve got some projects they’re working on. How would you respond? Would you say, “Why aren’t you going anywhere? Don’t you like to travel? Are you afraid of new places?” Or would you just ask them about their home-improvement projects? People who are good at conversation—and dating—know how to listen to one another and move with the flow. If your date can’t or won’t do this, I’d say it’s no great loss.
Sure, if things go well you’ll eventually want to divulge your dating history. Hopefully, your new love will have the maturity to respect that, even if your years alone weren’t exactly your choice, you did at various points in your life make the decision not to be in the wrong relationship. The right guy won’t find this off-putting. He’ll feel very lucky that you had the good sense to wait.