How to Answer Questions About Your Past Relationships on a First Date

“So … why’d the two of you break up?” she asked on their first date. “Was she cheating? Working too much? Not good enough in bed? C’mon, just tell me.”

“I, uh, well … it was, um, we had both started drifting apart,” he said before taking a large gulp of his wine.

Uncomfortable? If you said yes, think about how much more uncomfortable you’d feel if you were the one on the receiving end of prying questions like these. And from someone you just met, no less.

Well, this happens more than you may think on first dates, which can be the reason why those first dates also become last dates. That’s because personal questions about past relationships aren’t generally appropriate for this stage of dating.

So, how do you respond to personal questions about your past relationships when that not-so-special someone asks them? I have a few ideas.

Gently try and change the subject.

How open you are is a matter of personal preference. But as a matter of course, it’s usually better not to divulge too many details, especially about matters of the heart, to people who don’t know you well. That’s because they have no frame of reference by which to evaluate your comments, and you risk them getting the wrong idea about you.

Therefore, if your date starts to press you about information you may not feel comfortable discussing, your best bet is to try and gently change the subject. More specifically, direct the conversation to subjects you may be more comfortable talking about: your travels, where you grew up, your livelihood (in broader terms), and perhaps some of your aspirations.

What each of these conversation topics has in common is that you can approach them from a place of positivity. Past relationships, no matter how well they ended, can bring about negative emotions, such as sadness or anger — in you and the person you’re speaking to.

Come out and say that you’re not comfortable discussing your past relationships.

If the person you’re on a date with isn’t taking the hint, consider taking a more direct approach: “I’m not really comfortable talking about this. But I would love to hear more about how you …” And then ask them something about themselves. Or, again, try to divert the conversation elsewhere, perhaps to something you recently did or have planned. The important thing to remember is you don’t owe anyone an intimate view of your life, especially someone you recently met.

Now, I will warn you, there are those people who still won’t listen and will continue to press you. If the person you’re out on a date with still doesn’t want to honor your request to change the subject or just isn’t getting it, they’re giving you information about themselves that you need to carefully evaluate.

Make a decision about whether you want to consider dating this person.

At the extreme, if someone is making you uncomfortable on a date, whether because of the personal questions they’re asking you or any other reason, you always have the right to excuse yourself then and there.

However, if you don’t feel as though you’re in imminent danger but find their persistence anywhere from annoying to off-putting, you have a decision to make: Do you want to see this person again should they ask?

Having someone pry into your personal life, even after you’ve requested clearly and directly that they stop, could be a red flag and a sign of undesirable behavior to come. For example, this person could be controlling or emotionally abusive. Think about it. If they’re pushy about your past relationships at this stage of the game, what else will they be aggressive about, and when? You don’t need to wait around to find out.

Final thoughts …

First dates are the time to begin getting to know each other. The time when you can learn as much about a person from their answers to the questions you ask as you can from the way they ask questions, the type of questions they ask, and their reactions when they don’t get their desired response. I know it’s a lot to discern. However, it’s critical that you take a moment to assess what it is you’re learning from and about your date.

Your time is valuable as is your physical and emotional wellbeing. So watch and listen. Then, if you don’t like what you’re seeing and hearing, feel free to move on. There’s no shortage of eligible singles — if you have the right advice to guide you. Singles who will show you the courtesy and respect you want. And are waiting for you to show that to them, too.