6 Dating Conversation Killers and What to Say Instead

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Good conversation is what gets relative strangers to become people who have gone on a date together. I wish I had some deeper insight but seriously, the secret to dating success is in knowing how to move a conversation from open, to continuing, to date planning. You don’t even have to be that good at conversation really, you just need to avoid conversation killers. You all know what a good conversation starter is, right? Anything that you can ask a question or talk about without coming to an abrupt or awkward close. Anything that will very likely bring your conversation to a close is a conversation killer. Having sent and received thousands of messages on more dating sites then I care to name, I know a thing or two about how to avoid conversation killers, so here are the top 6 ones I can think of that you should immediately avoid, and what to say instead:

1. “Hey”

You kidding me bro? ARE YOU KIDDING ME BRO?! That’s all you got, a “hey” like I’m some dumb horse? Not just like a regular horse, but a REALLY not-smart horse who doesn’t know that they should be eating hay, so you have to point at it and yell “Hay!”. Seriously, this just a waste of time for you and me and everyone. Maybe you think you don’t need to try, or maybe you think that because you’re usually the one who receives messages getting a “Hey” message from you should make people happy. Nah, you’re both wrong. If you’re about to just send a message that says Hey, or Hello, or Hi, and nothing else, add pretty much anything to it after that besides “how’s it going?” and your message will be exponentially better. Instead, ask about something in their profile that they almost certainly included as a conversation starter. If their profile sucks, ask about something you noticed in their pictures. “Hey, noticed you like to travel. If you had to pick any place in the world to live besides here, where would it be?” works if they’re a traveller.  Pet pictures? Ask about the pet. Picture with their family, ask about that. Anything besides just saying “Hey”, except…

2. “Hey, how’s X?”

My day/week/weekend all went very well, thanks for asking! Seriously, no one is all that interested in answering this question, and asking it is doing neither one of you a favor. Instead, get more specific. If they’ve told you about a specific thing that’s happened, like a recent trip, ask about that. If you’re opening a message and feel compelled to ask about their day/week/weekend, include details relevant to the day/week/weekend. “Hey, how was your weekend?” is meh, but “Hey, how was your weekend? Did you get a chance to see the sunset on Sunday, it was gorgeous” is a bit better.

3. “Can you send some pictures?”

Assuming that the person that you’re chatting with already has pictures, but you’re skeptical that those pictures match the person you’re chatting with, what does them sending additional pictures do to prove who they are? If you can find 5 pictures of someone else and use them on your fake profile, what makes you think you can’t find 5 more?  More importantly, don’t you know how to use the internet? Tineye and Google Image search are your friend when it comes to catching Catfish. Also, if you’re using Tinder or Bumble, you already know someone’s name, and probably where they work, what school they went to, and their profession. Google them using that information maybe? It really is not that hard, and I do it all the time when someone seems too good to be true. I can find out if someone is legit by searching their name, job title, and not much else and it takes about 5 minutes to figure out if they exist or not. If you’re asking because you just want to ogle more pictures of them, you know porn is free and plentiful right? Oh and asking for sexy pictures before you meet someone is generally a bad idea. It’s a high risk/low reward move and, again, porn exists so it’s not like you’ll have a hard time finding sexy pictures because if you’re reading this, you’re on the internet. If you want to check to see if someone is a catfish, search their pictures, but you can also ask questions that require specific answers. If someone is on Tinder and lists their job as say, entrepreneur, but when you ask about their supposed entrepreneurial endeavors they seem reticent to discuss them in details, they’re probably bullshitting you. Fake users hate specificity and are generally responsive but vague.

4. “How’s your experience been on this site/app?”

A) Awesome B) Barely worth mentioning  C) Crappy or D) Don’t really have a strong opinion. Those are the answers you’re going to get. Got it? Good, now stop asking people these questions. Asking about someone’s experience dating online, while you’re talking to them on an online dating site is sort of like going to a concert and wearing the band’s shirt. You just don’t do it, nobody really gets why, but you just don’t. Maybe it’s too meta? Asking how someone’s experience on a dating site has been going puts you both in interview mode, rather than testing chemistry mode. Once you start asking those sort of question, it makes your conversation a bit more formal and impersonal. Instead, talk about literally anything else. Too vague for you? Fine. Ask about something tangentially related to dating in some way, but not about their dating experiences. Instead of asking what is essentially a question about your potential dating competition, instead ask if they’ve ever been to a specific date spot, or if they read Modern Romance, or anything else that would actually further a conversation.

5. Sex Talk (when it doesn’t match the tone of your conversation)

If you’re both just looking for sex and upfront about it, and are already talking about sex, get as raunchy as you want to be. If, on the other hand, your conversations are mostly around pretty standard getting-to-know-you things, when you start peppering your conversation with very graphic sex talk, you’re going to kill the conversation. You have to read the tone of the conversation. You can be flirty and talk about sex in roundabout ways if it matches the mood of the conversation. I’m as sex-positive as the next generally sex-positive person, but if I’m messaging someone about podcast recommendations and then they follow it up with questions about my sexual preferences, it’s going to put me off. You can get explicit if your conversations just sort of go that way, but if they don’t, try to ask questions about their experiences. You can find out if someone is GGG without asking explicitly if they’ve ever done butt stuff, or if they’d be into being choked during sex.

6. “So, why are you single?”

Because the last relationship ended? Because I am not currently in a relationship? Let’s pretend you get a meatier response than that, what’s it going to be like? “Oh, I’ve been single for about a year, mostly because my ex cheated on me with like 40 different women. So anyway, how about these wings, huh?“. Why someone is single is either going to get you a real answer, probably too real, or they’ll brush off the question. Either way, your conversation is going to head to a full stop. Instead ask how long they’ve been single, because that’s actual relevant information. You can also ask what they’re looking for so you can figure out if you’re on the same page, or even in the same commitment/non-commitment book.

I can’t promise that if you avoid all of these conversation killers that all of your conversation will go smoothly, but I can promise that at the very least, you’ll be doing your part to move conversations forward.

Good Luck Out There.

Demetrius Figueroa

Demetrius is a sex, dating, and relationship writer based in Brooklyn.

17 thoughts on “6 Dating Conversation Killers and What to Say Instead

  • June 28, 2016 at 1:36 pm
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    Great post. My WORST is ‘how was your day?’ Anything, ANYTHING, but that.
    And everything else listed above…

    Reply
    • June 28, 2016 at 2:07 pm
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      A good unwritten rule for conversations on dating sites is to never start a conversation with someone the way a coworker they don’t know well would. ex. How’s your day? How ’bout this weather? etc.

      Reply
      • June 28, 2016 at 2:39 pm
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        also, never be intimate immediately. keep some distance, be witty, interesting, a little mischievous. but not sexual!

      • June 28, 2016 at 3:16 pm
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        Great points! In my experience, even the people who are looking for something casual want a little bit of build up before you dive into the intimate sex talk

  • June 28, 2016 at 2:42 pm
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    Ugh, I always get the ‘How are you single?’ line.

    How am I supposed to answer that? Oh, I’m a bilingual attorney that can dance really well and make really great drinks……aaaand I also have attachment and intimacy issues and am usually in my own head more than is apparent on the outside.

    Yeah, great explanation. Another drink, please.

    Reply
    • June 28, 2016 at 3:13 pm
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      yeah it’s just such an ineffective way to get information you might want, and honestly the more direct questions would probably work better. How long have you been single? or Have you ever been married? or How do you feel about commitment? or pretty much anything more specific than “Why are you single?”

      Reply
  • June 28, 2016 at 2:59 pm
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    great post im going to log onto my fb and reshare this one-this is a great read for all the daters out there. Especially the send me pics one. I couldn’t stand that. For one we all know that is code for send me sexy pics and if i really want to move forward you can get your own in person so….. great advice as usual

    Reply
  • June 28, 2016 at 5:29 pm
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    I know the opening line is so hard – but it’s SO Important. It sets the tone for the entire conversation, so I gotta say – if you come out the gate boring, it’s gonna continue to be boring. I hate ALL of these are opening liners (and on Bumble us ladies have to write first and I really try to be better than this) but the WORST is “why are you single?” How TF am I supposed to answer that?

    Reply
  • June 28, 2016 at 8:26 pm
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    I love this post! I wrote a blog entitled “why are you still single?” and you’ve hit the nail on the head.

    Reply

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