when to ask those awkward dating questions

One of my favorite dating and relationship blogs, unemployedkat.com, written by a writing group buddy, Kat, inspired this post. Her latest post on “those awkward relationship talks” got me thinking even harder about something I’ve been contemplating: how and when to ask the “hard” questions on a date. You know, those questions where the wrong answer is a definite dealbreaker.

Basically, I also think it’s better to ask these tough questions sooner, rather than later. Sure, they might force you to get a bit vulnerable with someone you barely know, and the answer could determine whether you see them again or not, but this is all information that’s going to come out eventually, so why not today? Some questions are always tough to ask and could lead to a slightly awkward conversation where you don’t know a perfect way forward – but that’s true whether you aks them on date number one or date number five.


Version 2

In recent years, I’ve forced myself to start asking people on the first or second date when their last serious relationship ended. This is an important question to me and the more I like the person, the sooner I make myself ask this. I would rather know from date one if this person is emotionally ready for a relationship than go on several more amazing dates only to learn that they’re a few months out of a super serious relationship. Better to be disappointed by a stranger than someone I’ve been hanging out with for a few weeks and am starting to like, right?

Of course, there is much more to build on from this one “serious” question. I’ve been thinking about what other questions I want to or need to know early on in order to advance the person to the next round. What about simply asking them “What are you looking for?”

The way I see it, people who are actually looking for something serious won’t be scared off by these questions. In fact, they’ll probably be glad you asked them. And the ones who are visibly ruffled, or who don’t tell you what you need to hear? Well, that is super useful information to know right from the beginning, and information you can use to decide whether or not to see them again.

What other questions do you need answers to on the first date?


– la fille americaine


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