Dating is already nerve-wracking for some people, and you don’t want to ask something that will make him clam up or feel like he’s put on the spot. Some people are naturally shy and others aren’t fantastic at answering rapid-fire questions. Questions that can lead to confrontation or uncomfortable silences often fall into three categories: negative, judgmental and overly personal.

Dirty looks

Although you can never be sure how your date will react, you definitely don’t want to steer him down a negative route. That’s why asking about his exes or current single status might not be the best idea when you don’t know him well at all. You can’t know for sure whether your new guy has negative experiences with certain areas of your life, but you definitely don’t want to run headfirst into a downward spiral.

Secondly, some questions come off as judgmental or snobby. You’ll be painting a negative picture of yourself as someone who’s judgmental if you focus on how much money he makes or something that you think is wrong with his looks. And he won’t feel good about himself, either. Even if you’re not compatible, there’s no reason to make the time you spend together on a few dates uncomfortable.

Lastly, some questions will become appropriate as you get to know each other better, but they’re best left off the table for the first few dates. Getting to know someone is like peeling an onion. It’s slow, and you learn more as you peel each layer back. Save those heavy questions for later if you don’t want your date to clam up, possibly making it impossible for you to get to know each other at all!


Although you can follow our guide to avoid the awkward questions to ask a guy that’s too negative, personal or judgmental, we’ve curated the most awkward questions to ask, especially on a first date. Don’t make the mistake of bringing these questions up in conversation!


This question gives the impression that you’re a gold-digger right off the bat. You might be curious whether a guy is self-sufficient or whether he’s still living with Mommy and Daddy, but there are better ways to do that. For example, you might ask whether his dream job supports him well.


Most people are curious about the status of their date’s parents’ relationship, but this is a tricky question. If you’re not careful with tone and context, it might come off that you’re asking whether someone is messed up because of their parents’ divorce. You should also remember that just because a person’s parents are still together doesn’t mean the person is any good at relationships — or that the parents in question are happy.

Instead, try asking about his relationship with his parents and/or family. This question will lead him to naturally explain the nature of his parents’ relationship to each other, and it provides him a chance to tell you about his favorite family members and memories.


Unless you’re dead set on being someone who shares the same religious views as you do, you should stay away from this awkward question to ask a guy when you’re just getting to know him. Many people marry outside of their faith and make it work, and it can create pressure on the guy that you’re talking to if he’s not ready to explain why he does — or doesn’t — believe.


Just like you’d want to avoid discussing religion, questions about politics fall under the umbrella of awkward questions to ask a guy. Politics can be a deal-breaker, especially when election time rolls around, but they don’t make for polite dinner conversation. At best, you’re both apathetic, but you could find yourself arguing over the current political climate with someone you’ve just met before the main course is served!

Of course, if he mentions a current politician or law that he likes or dislikes, you can encourage conversation by asking if he leans to the left or right. Just be prepared for an earful if he’s the type of person who feels strongly about politics!


You never want to start a date by asking a guy what’s wrong with his appearance. Whether it’s his choice in clothing or even something that might be a birth defect, tread carefully.  The exceptions may be if he’s got an obvious injury.


This is a question to ask your bestie before you leave the door for your date and not a question to ask someone you just met. It sounds like you’re desperate for attention and compliments, so you won’t come across as an independent and confident person, which guys love. Plus, many guys feel that this question is a trap with no “right” answer! Check out this guide if you want to know you look good!


For some reason, both men and women ask this question early on, but it’s definitely the wrong thing to ask someone. It falls into the category of personal questions that may make him freeze up, and he may have had a recent negative breakup. Don’t assume because he’s still single that he’s always been single or that he has commitment issues. After all, you’re looking for love, too!


If you’ve only been on a date or two, it’s way too early to be concerned about where the relationship is heading unless you’re worried about an impending life change and it’s clear you’re both really into one another. Skip questions about how many kids he wants or what he imagines his wedding will be like, too!


Although non-circumcision can slightly increase to risk of transmitting bacteria infections or STIs — more on that here — this isn’t appropriate talk so early on in a relationship. Having sex with a circumcised man versus one who’s uncut isn’t that different, anyway. Check out this post to learn more.


It is important that you know whether your partner has STDs before you have sex or even engage in sexual contact that can transmit STIs. This allows you to use condoms and take other precautions. However, it’s not appropriate until you’re closer to becoming intimate. You may be able to work it into a fun conversation where you ask some of these questions.

This question may occur pretty early on if you plan to have sex on the first date. But that’s not for everyone.


While you probably want to consider the above list questions you’ll never want to ask a guy before you know him well, there are some questions that fall under the “maybe” category. These are the type of questions that can be a deal-breaker with some people, so you’ll need to ask sooner rather than later. You can probably skip these questions if there’s no chemistry and you know there won’t be a second date, but asking it within the first handful of dates will stop you from wasting time.

However, asking about whether someone has kids, smokes or is seeing other people early on can be a slippery slope. Carefully read the atmosphere before asking and consider how you can work it into conversation without seeming too irrelevant.


It’s not that you shouldn’t ask any questions when you first meet someone new. After all, that’s how you get to know someone. However, you don’t want to create pressure or start an argument, so you’ll probably want to stick to fun and light-hearted topics. These can include:

  • Hobbies
  • Work
  • Favorite movies, music and books
  • Friends
  • Goals

You can also count on complimenting him as a surefire flirting technique. Check out this post and this one here to up your flirting game, too!

eHarmony recommends asking insightful question that allow your date to open up and even realize a few things about himself. For example, you might ask what sort of things really make him laugh or who was his most influential teacher as a child. Both of these things allow you insight into his personality, but they’re also positive topics that he will probably enjoy answering.

You’ll want to pay attention to his verbal responses and body language so you can steer away from unpleasant conversations. And if there’s a subject that makes his eyes light up when he talks about it, ask more questions! He definitely won’t mind.

You won’t be able to pay attention if you’re too busy formulating your next question, and you may even miss out on something he’s trying to express. It’s okay if you listen to his reply and pause to gather your thoughts. In fact, it can come off as thoughtful! Plus, not every moment needs to be filled with speaking.

Hopefully your conversation will naturally progress on its own so you won’t have to prepare your next question too hard, but the questions above will create a foundation you can work from as long as he’s not too uncomfortable or clammed up.

Now, there may certainly come a time when some of these questions are important. For instance, if you decided to move in with your boyfriend and want to figure out how to split bills, you’ll both need to be open about your finances. In fact, as one or both of you become more comfortable around the other, you may find yourself naturally answering some of these questions. However, these aren’t the type of questions you want to ask to someone whom you first met or on a first date.

He might break the mold by asking you some awkward or personal questions right off the bat. Of course, you can simply tell him that you don’t believe you know him well enough to answer those questions yet, as he should feel free to do with you. But if you pay close attention to his comfort level, you might know whether some of the questions are appropriate or you may be able to word a risky question in a way that’s relevant.

Avoid questions that will make things awkward outright, especially if this person is a friend or a coworker who you’ll see in the future even if you don’t continue dating. Otherwise, have a good time and try to avoid any awkward question to ask a guy. Rest assured that any guy who’s really into you will be able to navigate around communication mishaps that might occur. After all, everyone gets nervous or flustered, and being genuine goes a long way!

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