Home Love & Relationship 15 Awkward Questions You Should Never Ask a Guy

15 Awkward Questions You Should Never Ask a Guy


Open communication might be the cornerstone of any healthy relationship, but that doesn’t mean you should ask just any question that pops into your head. Some questions that might seem harmless to you can actually create some really awkward situations.

Of course, every man is unique in some ways, and different men can handle different questions. But if you’re still in the early phases of a relationship and still figuring out what you should talk about then there are a few questions you should avoid. We’ve prepared a list of fifteen you should steer away from if you want your dates to go smoothly.

1. Do you think she’s hot?

Men are only human, as long as you’re dating a straight man with an active sex drive he will look at other women and think they are attractive. That does not mean that he’s going to run off and leave you behind. There’s no way this sort of question can lead to anything good.

He might lie to make you feel good, or he might tell you the truth and make you feel self-conscious. Your guy is going to look at women and think they’re hot, what you need to worry about is if he stares too long or if he seems like he’s going to act on those feelings.

2. What kind of woman are you into?

Everyone has a long list of things they are into sexually. Nobody finds a person who checks off everything on those long lists. It doesn’t help that most people have contradictory lists. How many guys out there want a girl who has a stomach as flat as a super model’s even though they don’t like the feeling of bones poking into them when they’re cuddling?

If you ask your man to describe what sort of things he’s into and he responds honestly, he’s eventually going to name traits you don’t possess. There’s no need to worry about this nonsense. Just know that if he’s with you he clearly thinks you’re worth his time and affection even if you aren’t the impossibly perfect woman of his dreams. He’s probably not the impossibly perfect man you always dreamed about, that’s life.

3. When are we going to get married?

Talking about marriage is healthy at some point in the relationship, but you have to be careful about it. The last thing you want to do is pressure him into making a decision he isn’t completely confident about.

These things need to happen in their own time. You can drop hints but don’t pressure him. You want a man who will propose to you out of love and commitment, not out of guilt and obligation.

4. What’s your paycheck look like?

OK, if you are getting married to a guy you might need to know something about his finances, but until then you don’t want to give him the idea that you’re a gold digger.

It’s not wrong to want a man who can support you, but you don’t want to make a man think that you only want him for his money. On the other side of thing, people who don’t make much money don’t like people looking down on them. So just steer clear from financial discussions until you start thinking about a joint checking account.

5. Why don’t you get a better job?

You might think you’re being encouraging, but in most cases this will just make the guy feel bad. Few people feel they are making as much money as they deserve and everyone has reasons why they aren’t rich.

You can encourage him to follow his dreams but if he’s content with how things are then you should try and see things from his perspective.

6. What annoys you about me?

Be careful what you ask for. The problem is that sometimes the things that annoy us are the things that other people can’t change.

You might find out that there are little things about yourself that annoy your man even though you have no power to control them. You’ll have no choice but to let your new-found knowledge eat away with you for the rest of the relationship.

7. What’s with your body?

It’s easy to think that men don’t have any body image issues. To be fair, the media isn’t nearly as hard on them as they are on women, but that doesn’t mean that all men are walking around like they are Adonis in the flesh. If your man has some extra meat on his bones he probably already knows about it and doesn’t need you reminding him.

8. Would you give up something you love for me?

Everyone wants to feel like their partner puts them first, but that doesn’t mean you should try and force him to choose between you and his interests.

If he’s neglecting you, then it’s worth bringing up how you feel, but don’t just put him in an awkward position just because you want to feel better about yourself. Believe me, you don’t actually want a guy who has nothing going on except you, those sorts of relationships are smothering and unhealthy.

9. Why do you hang out with him?

Your man’s friends were probably there for him before you were and if you break up with him his friends, we’ll be there when you’re gone. Going after a man’s friends is not a good way to get on his good side.

It’s healthy for a man to have a support group outside of his relationship. To be fair, if his friends mistreat you, then you need to stand up for him. Just be careful about trying to reshape his social group to your liking. He doesn’t have to like all of your friends, and you don’t have to like all of his.

10. How many notches do you have on your bedpost?

In case you don’t know, this is another way of asking someone how many people they’e slept with. Everyone has a past and sometimes it’s best if the past stays where it is.

If he wants to tell you about his sexual past, he will. Think about it this way, do you really want to imagine him sleeping with other women? Because that’s what you’re going to be doing after he answers this question!

11. How big are you down there?

It is what it is. There are few things that men are more sensitive about. The big issue for men is that there’s nothing they can do to change this part of themselves. Despite all the efforts of men throughout thousands of years of human history, they’ve never come up with an effective way of enlarging their manhood.

So, whatever size it is you either accept it how it is or find someone who matches up to your expectations. Making him feel self-conscious isn’t going to help either of you.

12. Why aren’t you like this other person?

No one likes to be compared with other people. Men and women both have to struggle with all sorts of self-image issues and comparing your boyfriend to other men who might have things that he doesn’t isn’t going to help his psyche.

You should also remember that turnabout is fair play, and if you start negatively comparing him to other men, then he might start telling you about all women who do things better than you. It’s not a path you want to get on.

13. Do you know how unhealthy that is?

Chances are they know that what they’re doing is unhealthy and they’re still doing it. Everyone has their vices and you have to decide if you can live with your man’s.

This doesn’t mean that you should stick around a man who is very unhealthy, just realize that criticizing him is more likely to lead to a fight then healthy behavior on his part.

14. Who is the one person you’d like to cheat on me with?

Some people call this “picking a freebie.” This is a game people like to play because it usually involves naming celebrities. After all, what’s the harm in fantasizing about unreachable actors, artists, and athletes?

The problem is that not everyone knows how to play the game. Sometimes you will tell your boyfriend that you want to cheat with Brad Pitt and he responds by telling you that he wants to sleep with your best friend. It’s better of avoiding the topic at all.

15. What would you do without me?

This is another question without a good answer. What answer would make you happy? Do you really want a guy who has no life outside of you and would just turn into a puddle without you around? On the other hand, it always hurts when you realize that the person you love could live without you.

But that’s just the way it is, unless you met him in the maternity ward you both had lives before you met and you’d be able to go on living without each other. That doesn’t detract from the time you’ll share with one another in any way. So don’t try and travel into a dark future, enjoy what you have together now.


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