7 Awkward Questions You Should Never Ask Your New Guy

7 Awkward Questions You Should Never Ask Your New Guy

Awkward questions to avoid when chatting up your new beau—you know, so he doesn’t turn into an old beau.

Dating is already a nerve-wracking experience, so why throw awkward questions into the mix that make him feel like you’ve just stuck his penis on a chopping block? There are some questions that have been part of the female vernacular for so long, we don’t realize they put the guy we’re dating in a legit lose/lose situation.

Some awkward questions may become appropriate after you’ve dated for a while, while others… well, not so much. Here are 7 you should totally avoid:

1. “Why did you break up?”

The last thing either one of you wants is to bring old baggage into a new relationship, and there’s no way the answer to this question will bode well for the two of you—especially if they broke up because of something he did. All that matters is that he’s now with you, and your relationship is the only one you should be focusing on.

2. “Do you think I look fat?”

What this question means is you think you look fat. You’re not looking for feedback here—you’re looking for him to put the kibosh on your insecurities (which is totally unnecessary because you’re fabulous as-is).

3. “Where do you think this is going?”

When you’ve only been on a few dates, what’s there to figure out so soon? The only way this question would ever be okay is if you’re worried about how an upcoming life change (such as a potential move) is going to impact your dynamic—especially if it’s clear to both of you there’s serious potential.

4. “Notice anything different?”

If he doesn’t bring up how amazing your two new highlights look on his own, the answer is no.

5. “Who was that?”

If you’re a totally open book when you get a text or IM, that doesn’t mean he’s going to be. It also doesn’t mean he’s being devious or hiding things from you if he doesn’t spill the details every time someone contacts him.

6. “What’s wrong? Really? Are you sure? What’s really wrong?”

If something seems a little off, asking him what’s wrong is totally fine, but only once. If he wants to talk about it, he will. If he doesn’t, he won’t. But the more you try to pry it out of him, the more he’ll pull away.

7. “Do you think she’s hot?”

If he says yes, you’ll want to run him over. Twice. If he says no, you’ll assume he’s a liar, then you’ll spend the rest of the night panicking about all of the other things he’s “hiding” from you. Don’t set yourself up for the shortest relationship in history.

Are there awkward questions you’d add to this list?

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Couple sitting together image via Shutterstock

Krissy Brady

Krissy Brady is a women’s health + lifestyle writer who’s so out of shape, it’s like she has the innards of an 80-year-old. Instead of learning how to crochet, she decided to turn her emotional baggage into a writing career (genius, no?). You can follow her shenanigans on Twitter (you know, if you want).