A Big Girl Rant: The 5 Most Annoying Questions in Dating

September 18 2009 | CeCe Olisa

Let me begin by saying that I love dating.

I love the awkwardness of being asked out, I love saying yes, I love the anticipation of a date night, the excitement of choosing an outfit and I love spending a few hours with someone new who is focused on getting to know me and then seeing what happens.

As someone who often learns a lot about people just by listening to them talk, one of my pet peeves in dating is when the date turns into an interview. I hate when it becomes obvious that a guy has a set list of questions that he asks every girl. But I find that this is happening more and more… so I have compiled a list of The Five Most Annoying Questions in Dating.

I’m sure there are many more, but these are the ones that I hear over and over again:

Number five…

What do you do for fun?

Okay, I get it– you’re trying to get a feel for my interests, but I can assure you, I don’t categorize my life’s events under “fun” or “not fun”. I’ve never called my girlfriends and said “do you want to go have some fun?” So a question like that, to me, is very strange.

The other day Robert and I went to Bed Bath and Beyond because I wanted new curtains. They didn’t have what I was looking for, but we ended up spending a ridiculous amount of time in the store doing random things like sitting in the massage chairs talking and carefully selecting the perfect lint roller. We had a blast, but if I told someone that I go to Bed Bath and Beyond “for fun”, they would look at me like I was nuts.

I guess for me, it’s not what you’re doing; but who you’re with that makes life fun.

Number Four…

What kind of guys do you like?

As a PSP of course I’ve wondered if guys who have been interested in me have dated big girls before, but I also know that finding out all of his exes are Beyonce lookalikes wont do anything but make me self-conscious. So, I dont ask. But I know that when the time is right, and if its relevant to our relationship… I’ll find out.

Why does it matter what kind of guys I’ve dated in the past? If you have me on an actual date, there’s one reason I’m there… You. So, if my last 12 boyfriends were NBA players and you happen to be 5’1, that’s irrelevant. Even if all of my exes happened to be loud and arrogant and you’re quiet and humble, its irrelevant. If the kind of guys I usually go for were what I needed, I would still be with them, so do us both a favor and give me space to discover something new in you.

It’s like they say: If you always do what you’ve always done; you’ll always get what you’ve always gotten.

Number Three…

Do you live alone?

Usually, when I’m asked this question I will respond “why do you ask?” to which the guy will say “I was just wondering…” But let’s be real, when a guy is inquiring about your living situation it’s probably because he’s trying to gauge how soon it will be before he’s in your apartment and more importantly your bedroom.

(The funny thing is, guys assume that girls who live with roommates won’t be as quick to invite them over. But I’ve definitely heard all of my previous roommates having sex at one point or another.)

This question just shows that a man is calculating how soon we’ll be hooking up, which is just tacky.

Number Two…

So… you like ________ guys?

This question is a little different from “what kind of guys do you like?” I mostly hear this question when I’m dating interracially:

So… you like Asian guys?
So… you like Indian guys?

I’ve also heard it once when talking to a guy who was overweight:

So… you like big guys?

Maybe my issue is just that I don’t like stupid questions. If you are Asian and I’ve agreed to go on a date with you, isn’t it a safe bet that your race isn’t important to me? I’m not going to go out with an Asian guy only to tell him “No, I do not like Asian guys.”

Why make me state the obvious?

And finally, Number One…

So, why are you single?

*deep sigh*

This question is #1 because it is so ridiculous!

My typical answer to this is pretty literal “I’m single because I don’t have a boyfriend.” To which the person who’s asked the question usually realizes how silly the question is. Then they all reply with the same predictable response “Well, its just that you’re so beautiful—I’m surprised no one has snatched you up yet.”


I don’t think guys realize that it sounds like an accusation. Why are you single? Why can’t you get a man? How come no one wants you?

Again, I ask; what am I supposed to say to that? I mean, should I say “I’m single because I refused to sleep with the last guy I dated after six weeks”? or I could say “I’m single because the last guy I was interested in wasn’t attracted to a woman of my size”, maybe I should scare them off and say “I’m single because I tend to stalk the men I go out with if they dont call me”. I dont know….

What I do know is, I hate this question with a passion.

The crazy thing is– when men ask “why are you single?”, they all are expecting the same answer. You see I’ve gotten so very tired of this question that I’ve started to probe every man who uses it. I’ll ask, “What do you think is a good answer for a question like that?” and 100% of the time, these men offer the same response: “I just haven’t found the right one yet.”

So, if this is a script that has been played through a million times with no variety, why do they continue? And am I a bad date if I dont want to deliver predictable lines?

Anyway, these are my top five, what bad/offensive/awkward questions have YOU been asked?

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26 responses on “A Big Girl Rant: The 5 Most Annoying Questions in Dating

  1. Deidre

    I hate "what are you looking for in a guy". What is up with that question?

    I also, since living in Australia, get a lot of questions on how I can afford to live here without a job. I feel like it is totally rude to ask about someone's finances on the first date. I've taken to joking "I busk and sell my body for sex on weekends"…they generally don't find it funny.

  2. Dating Trooper

    Great post!

    The "why are you single" one is the worst….I absolutely take it as an accusation whether they mean it that way or not.

    The "what do you do for fun" one is also awful. The moment someone asks it, it's as if every fun thing I've ever done gets sucked out of my brain and all I can think about is standing in line at the DMV or something. Of course, until reading this, it never occurred to me that I could turn it around and imply that it's a DUMB QUESTION in the first place!

    But then, I don't enjoy dating. That's why I call it warfare!

  3. Anonymous


    My friends give me a hard time for not wanting to answer these questions. I'm being to harsh, they're just trying to get to know me… sure, then come up with some intelligent questions.

    The last guy who asked me, "why are you still single", I politely reflected the question back to him, "why are you not married?"

    They get it after that and 90% of the time the date moves along on another level of mutual understanding that stupidity is not allowed.

  4. Jenn

    Any question referring to exes or when was the last time I got laid/how often I think of sex is pretty annoying for first/second dates. That's something a gal will tell you when she thinks you should know, if she ever thinks you should know. I think talking about an ex = desperation on someone's part anyway.

  5. Cathy Benavides

    Since I’m recently single and getting back into dating, I am encountering all sorts of crazy/annoying questions. My least favorite is “So are you looking to settle down?” I hate being asked this because I feel like there is no good answer. If I say yes, then I’m desperate and looking for someone to marry me in a month. If I say no, then I’m a party girl who doesn’t know how to commit. I usually just respond with a joke, but it annoys me to no end!! I’m looking to date and meet new people until I find someone I connect with and want to share my life. Great post!

  6. notgirlygirl

    Maybe it’s me, but I don’t think question #5 is weird. I ask that myself of men I’m getting to know. I want to know what you do on your down time…maybe we have interests in common. I’ve been fortunate that the other four have not been asked of me–however, part of why that’s the case is that many of the dudes I talked to weren’t interested in anything beyond sex. So take that as you will…

  7. Maruska Morena

    I am so glad someone else hates the “What do you do for fun?” question. I’m so like you in that regard.

    I also have an extreme dislike for stupid questions and “whats your favorite..” (as if I constantly go around ranking things 1-10)

  8. Emma

    Your hatred for those questions are SO spot on. Number 1 I’m always tempted to reply “I haven’t found anyone that is good enough yet.” But I don’t think that would go down well.

  9. MiamiTeddyBear

    @Cathy Benavides: If a guy asks you if you’re ready to settle down, he’s asking for a reason. Why would saying “yes” mean that you’re desperate? Saying yes simply means that you said yes to the question. If the guy is looking to settle down, this is an important question to see if there is long-term potential or if you’re just looking for short-term fun.

    @notgirlygirl: Thank you! I really don’t see what’s so wrong with the “what do you do for fun” question. If I ask this question, I’m trying to see if we have some hobbies, activities, or other interests in common.

  10. LaShanta

    I don’t like any of those questions. My answers, when asked, are normally whatever flies outta my mouth without any regard for how the guy is going to feel about the answer, or think of me for answering in that manner. Why would you NOT tell the guy how that question makes you feel if it bothers you? You’ll be sitting on a date, you probably wanna tell off. Just put the answer you have in your head on the table and let him pick it up or leave it as it goes. Cathy said: ” I’m looking to date and meet new people until I find someone I connect with and want to share my life…” and I think that’s an absolutely PERFECT answer to the question “Are you looking to settle down.” There’s no need to say yes or no to such a question, if the answer isn’t one of those. Just be real with your answers on your dates, if that dude doesn’t like the answer, you can always tell him you detest the questions.

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