By: Stephanie - Posted on: 10/11/2010

Top 5 Most Uncomfortable Questions Asked On A Date…And How To Answer Them!

It is inevitable that dates are not always going to go movie-style smooth. Slip-ups are bound to happen and you may trip and fall or spill food on your shirt, but there are some questions that drop your jaw permanently and leave you speechless for far too long. Although these questions should NEVER be asked, they have been, and you’d be surprised to find that a lot of people do not know how to answer them. Here’s a list of the top 5 most uncomfortable questions asked while on a date and how you should answer them!

5. Do you have any STD’s?

Surprisingly so, you might be asked this more than you would think. New developments in education have made it almost a necessity to ask this beyond awkward question. I mean, really, how do you answer that without slurring your words or turning bright red?! Here’s how I’d say you should go about the situation: if you have an STD, start packing your things to leave…but tell the truth. If you don’t, be conscious of your facial expressions and try to say “no” without sounding completely guilty while continuing to ask the same question back… maybe they are trying to tell you something…

4. So what happened with your last relationship?

It may not seem like that dangerous of a question but what happens when your last relationship ended because you did something bad or because you were a complete jealous psycho?! Picture your dates’ face when you answer that question with “well I cheated on him/her multiple times with his/her best friend and he/she found out and broke up with me” or “I don’t know what happened, he/she caught me ONE time outside of his/her house spying with binoculars…” I can imagine with each scenario that your date would be completely turned off. So what do you do if this question is asked while out on a date? Shrug it off; tell them that it just didn’t work out and that you are moving on to bigger and better things.

3. Have you ever explored the other sex?

Guys, this one is for you. For girls it may be sexy if they’ve dabbled in a little girl on girl make out session but for guys I’d say it’s the complete opposite…a total deal killer. The girl will be left wondering how she could have missed that you are obviously gay. She will want to be your best friend…but the rest is off the table.


2. What do you do for a living/what do your parents do for a living?

Money is a very touchy subject. This is absolutely one thing you should never bring up. However, if you are asked this question, it is best to avoid it. If you respond sounding snobby, it’s a turn off. If you respond sounding like you don’t have money, then the conversation will get 20 times more uncomfortable and your date won’t know what to do. So when you are asked this question you should just shrug it off and respond with a “I think it’s a little inappropriate to discuss that” and move on to the next subject. That will assure your date that he/she messed up and they will never ask that question again.

1. Are you Democrat or Republican?

This is the number one no-no. Political party talk can get extremely heated and you don’t want to risk a potential argument. Imagine you’re having a nice dinner with great conversation and then BOOM there’s the question. It might catch you off guard but I’m here to tell you that there is a right way to answer it and that is DON’T answer it. Save questions like these for when you actually like each other and it wouldn’t be as much of a deal breaker. If you’re feeling brave, though, and really want to answer this question…do so at your own risk.

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  • Matt Dibble

    I no longer date, but if someone gets upset over #2 and tells me it’s an inappropriate question, I’m going to immediately assume they’ve got money issues or something to hide.
    Talking about your jobs or careers is natural and good “break the ice” discussion that is silly to avoid.

  • Ara Kazanjian

    Clever thoughts. I’d add that these warnings apply to any new relationship…business or personal.

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  • Tiggerlille

    If someone freaked out over #2 I’d think they were a freak!

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