--- title: Online Dating: What to Say in Messages to Women description: I was having brunch with some girlfriends the other day, and we got on the subject of first dates. While we all had different experiences,... canonical: https://time.com/106690/worst-questions-women-online-dating/ author: TIME article:opinion: false article:content_tier: free article:published_time: 2014-05-23T11:00:12.000Z article:modified_time: 2026-04-13T08:55:20.377Z og:title: The Worst Questions Women Get When Online Dating og:description: I was having brunch with some girlfriends the other day, and we got on the subject of first dates. While we all had different experiences,... og:url: https://time.com/106690/worst-questions-women-online-dating/ og:site_name: TIME og:image: https://static.time.com/v3/assets/bltea6093859af6183b/bltb20b40a059279d72/69869044adae4447ae543307/450772629.jpg?branch=production&width=1200&quality=75&auto=webp&crop=16:9 og:image:width: 5122 og:image:height: 2881 og:image:alt: 450772629 og:type: article twitter:card: summary_large_image twitter:title: The Worst Questions Women Get When Online Dating twitter:description: I was having brunch with some girlfriends the other day, and we got on the subject of first dates. While we all had different experiences,... twitter:image: https://static.time.com/v3/assets/bltea6093859af6183b/bltb20b40a059279d72/69869044adae4447ae543307/450772629.jpg?branch=production&width=1200&quality=75&auto=webp&crop=16:9 ---  # The Worst Questions Women Get When Online Dating > Sponsored content. Supplied in partnership with TIME. 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Worth Your Time is TIME's culture newsletter, published Tuesdays and Saturdays to 40,000 subscribers as of August 2026. #### Who writes TIME's culture recommendations? Culture editor Eliza Berman writes Worth Your Time, drawing on TIME's critics and culture desk. #### Is Worth Your Time free? Yes. It is a free newsletter available at time.com/newsletters. by [Refinery29](https://time.com/author/refinery29/) ## Refinery29 May 23, 2014 11:00 AM UTC  Keyboard with red heart on button, close-up Keyboard with red heart on button, close-up Vstock—Getty Images/Tetra images RF by [Refinery29](https://time.com/author/refinery29/) ## Refinery29 May 23, 2014 11:00 AM UTC I was having brunch with some girlfriends the other day, and we got on the subject of first dates. While we all had different experiences, there was one thing we all agreed on: There are a few questions we are absolutely _tired_ of hearing from guys on a first date. Here they are, in no particular order. What do you do for fun? It’s a generic question that breeds generic answers, and doesn’t really give you additional insight into who I am. Asking me what I “do for fun” kind of makes me feel like I’m on an interview, not a date. Some of you may be thinking that this question means the guy is trying to plan a future date for us. I really wish you were right, but that’s what makes this question extra annoying: The same guys who ask me what I to do for fun will turn around in two weeks, and ask me what I would like to do for our first date, even though I’ve given them a list of things I do for fun. It makes no sense to me! So, why are you single? There is no faster way to make me feel like I’m failing at life than to ask me why I’m single. I mean, what is the right answer to a question like this? Should I say, “Well, I don’t hook up right away, so most guys get bored with me, and that’s why I’m single!” Or should I say, “I get really clingy around month three and it scares guys off, so here I am, solo!” The world already gives single girls the side-eye; there really is no need to bring up singledom on dates. You’re so pretty, I’m surprised someone hasn’t taken you off the market! (aka, “Why are you single: The Remix) This is one of those [backhanded compliments](http://www.plussizeprincess.com/2013/07/youre-confident-backhanded-compliment/) that really has no response. When men say this to me, it makes me feel like something is wrong with me — especially because 99% of the men who use corny lines like this will not make any moves to take me off the market. What kind of guys/girls do you like? This question is tough, because I understand it. As a Plus-Size Princess, I often wonder if the guys asking me out have dated big girls before (not that it matters, but I do wonder), and I’ve learned that the answer is rarely helpful. If his last three girlfriends looked like Jennifer Lopez, I may feel insecure, but if his last three girlfriends looked like Rebel Wilson, I might wonder if he’s a [chubby chaser](http://www.plussizeprincess.com/2014/04/dear-closet-chubby-chasers-go-away/). On the flip side, when a guy asks me what kind of guys I like, I might feel uncomfortable, especially if he doesn’t fit my normal boyfriend mold. I don’t want to have to tell Kevin Hart that my last three boyfriends were NBA players. That’s awkward, and irrelevant. In the end, knowing a person’s “type” really doesn’t matter as long as they’re attracted to you. So, do you like _(adjective here)_ guys/girls? This question is a little different from “what kind of guys/girls do you like?” As a plus-size woman of color, I hear this question in two scenarios. Either the guy is trying to see if I’m cool with him not being black, or the guy is trying to see if I’m cool with him being skinny. For me, the answer is always the same: “I like all types of guys.” I mean, if I’m on a date with you, it’s because I’m open to dating you, no matter what you look like. Why did your last relationship end? So, are you trying to make me to cry on our first date? This is information you’ll get eventually, but maybe we can keep it light and positive on the first few dates, please? Do you live alone? Seriously, why does a man need to know if I live alone? In my opinion, this question just shows that he’s calculating how soon we’ll be hooking up, which is just tacky. If you’re someone who has trouble making small talk on dates, one of my tricks is to start with current things, and go from there. Meaning: Instead of asking “What do you do for fun?” I’ll ask “What did you do this weekend?” and from there, I’ll get to learn what the person enjoys doing in their free time. Instead of being in the moment and asking about things based on the person we’re with, people come with these dating interview questions that they use on everyone they’ve ever met, and expect sparks to fly with generic inquisitions. Meh. I call these annoying dating questions, but they might just be lazy dating questions. Have you had any of these questions on dates? How did you respond? [RELATED: What If Your SO Didn’t Like Your Body? ](http://www.refinery29.com/body-hating-relationship) _On her blog,_ [_Plus Size Princess_](http://www.plussizeprincess.com/)_, CeCe Olisa has detailed everything from what it’s like to be the only big black girl in a yoga class (fine, thanks!), to_ [_her adventures in plus-size dating_](http://www.plussizeprincess.com/dating/) _in the Big Apple. Now, the New York City transplant is lending her poignant, often-hilarious voice to R29._ [This article was written by Cece Olisa and originally appeared on Refinery29.com](http://www.refinery29.com/first-date-questions). ```json [{"@context":"https://schema.org","@type":"NewsArticle","@id":"https://time.com/106690/worst-questions-women-online-dating/","mainEntityOfPage":{"@type":"WebPage","@id":"https://time.com/106690/worst-questions-women-online-dating/"},"headline":"The Worst Questions Women Get When Online Dating","datePublished":"2014-05-23T11:00:12.000Z","dateModified":"2026-04-13T08:55:20.377Z","description":"I was having brunch with some girlfriends the other day, and we got on the subject of first dates. 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