When do you try to keep a conversation going?

18 comments

1. I am a woman and I have the same problem with a lot of guys. Sometimes I assume that he meant to ask ‘And you?’ at the end of his message just to keep the chat going!

   If I get low effort messages twice in a row then I just let the conversation die

2. >Problem is, often they match, literally answer the question but don’t ask a question in reply or offer any other information.

   I directly talked to someone who did this to me. He told me he did it a lot because he was bored. He even to the point said he was playing music and home in his apartment after work bored and lonely. That’s it really.

3. As other commenter said, I’d try to give them a chance to actually show they are interested try another message, try to push the conversation.. and if they still come back with little to nothing to work with you can assume they arent for you just based on their lack of interest/incompatible communication style to yourself. Its also certainly the case that you are 1 in 500 for most of these women, but if they arent going to put in any effort, I wouldnt waste mine.

4. I find it so frustrating. Like, bro, WHY are we here if we’re not trying to get a match goes somewhere… HOW am i supposed to get an inkling if I’m interested in you as a person if we’re not finding things out about each other?

   I’m a very curious person and my peeve is when I ask questions and don’t get any in return. Especially over text since you can’t really just start telling a story about yourself out like you can in person (something that I don’t love doing anyway).

   I hate online dating, it’s brutal out there.

5. For many women, yes, you’re just one in 50 or 100 or 2000. That’s why it’s really important that your messages are good banter – they’re either thoughtful or witty or funny or inspire a message back – something that would make you stand out from the plethora of ‘hi, how are you’ ones we get inundated with.

   My male friends have told me that messaging women on OLD can feel like pulling teeth in terms of their level of effort to reciprocate, so it’s definitely not just you. I think as a whole, a lot of women are frustrated, bored, spoiled for choice, or just not used to having to work very hard at messaging because we get a lot more matches in general.

   I’ll say that personally, any messages that directly referenced specific items in my profile in a humorous way (not just observations like, ‘oh I noticed you like video games’ but something punny or cheeky) , always got me to check their profile, and 7/10 resulted in a message back.

   If after two rounds of texts, they’re not asking questions back, I leave the chat. Basic conversation skills and banter are a dealbreaker for me, and it literally takes 1% effort to type, ‘what about you?’ as a lazy way to keep it going.

6. If the lady is at all desirable she likely has tons of people trying to get her attention and who knows how many conversations they might be trying to juggle at any given time? This could help explain short/underwhelming responses.

   You need to somehow stand out of the noise. I understand asking questions based on the profile, but there is a high likelihood many other guys are doing similar and it’s starting to become tiresome for her to answer similar questions over and over. That also could help explain short/underwhelming responses.

   You need to try to get her hooked on a topic she cares about so she begins to invest more into your chat and start ignoring some of the other distractions. I know, easier said than done!

   Maybe try to find something more obscure about her profile to try to leverage into a conversation. Does she have a lot of travel pics? Maybe instead of asking basic questions (how did you like that place? Where do you want to go next?) You could try asking what her most unusual airport experience was – something that kinda forces her to share more info than just yes/no type answers that many others could be asking her.

   And of course, she still might not bite and that’s just the sad nature of the beast. But at least you start cracking your mind open to try different approaches and hopefully you’ll eventually make a connection with someone!

   Good luck out there – we all need it!

7. For what it’s worth I’m a heterosexual woman and I also live in LA and I’ve found the same thing messaging men. The last time I was using dating apps I was new to the city so I decided to ask all of my matches “What is your favorite thing to do in LA?”, which I thought was a fairly specific question that could get a conversation going, but I got a lot of one or two word answers like “chill” or “hang out” and very few returned the question. I didn’t bother to try to continue the conversation with those matches. I don’t think it’s a gender thing, probably a lot of people are just lazy and/or boring.

8. I bail almost immediately. If it’s not happening on the app when the initial introduction is there, it probably won’t happen in real life. It’s worked great for me. Just had a woman like me first, then messaged me right after we matched. This was like Saturday morning. We chatted about cooking and food, opportunity was there so I asked her out within 8 messages to meet up Tuesday. We texted non stop til then…met up, and instant chemistry. Talked at the bar for 2+ hours.

9. It depends – if you’re asking a really specific question about something on their profile, they might not be able to ask you a question back without totally changing the subject. So in that instance if you think about it like a verbal conversation, it may make sense for you to reply. Of course that shouldn’t be happening a lot.

   You can probably feel in context of the conversation when it’s time to stop trying.

10. I use the apps to get dates, not have conversations. I’ll match, maybe have a little back and forth, and then we either exchange numbers or agree to a date.

    A part of the probably that you lead with questions. People don’t like to answer the same boring question for the fiftieth time just because some stranger wants their attention. You don’t have enough buy-in at that point. I’ve found it’s far better to say something provocative, interesting or funny.

11. If a woman isn’t sending an open ended question back to you when you ask her one isn’t a good conversationalist and probably isn’t a very giving or interesting person.

    My dad is the most amazing conversationalist and taught me how to make every person I talk to feel the like the important, interesting, and seen person there is. If a woman doesn’t have those skills online, she’s probably not going to be much better in person.

    Part of the point of online dating is to eliminate what you don’t want so you can narrow the field to what you do want. Pics and profile bios are one test. Texting is another. If they can’t pass the basic tests of being an interesting person, you’re probably wasting your time with them. Move on to someone better.

12. Some people just don’t know how to carry a conversation as well. I try not to bombard a conversations, let there be an even flow of back and forth. For example:

    Last week a girl liked me on hinge. She’s cute, her IG has lots of pictures of cars. Plus 1 in my head, however, she’s lives about 4 hours from me. Yuck, but who knows. She liked my question prompt on my profile that “I’m convinced that…Women just want guys for their hoodies” and she responded with that she would just look homeless in a hoodie. Odd response, but it’s something. So on her profile she has that she used to breed snakes for a living. 😳😳
    So I said she’s brave for handling that profession. She said not really.
    I then said “I would be out so quickly if that was my job”…meaning I’m terrified of snakes.
    And no response after that. Two days later she deleted the chat. Didn’t bother me considering the distance between us.

13. To your last point, don’t worry about what other people are doing on the apps. It’s never occurred to me to start wondering how many other people a guy is talking to, or how many matches he gets, or whatever. Why would that matter to me? The only thing that matters is the connection that I’m building (or not building) with him.

    You’re just going to get in your own way if you fill your head with thoughts like that.

14. If a conversation starts lagging early I throw out “Tell me 5 interesting or unique things about yourself” (but make sure you have 5 GOOD ones about yourself also) This does multiple things.

    The biggest is it weeds out scammers. A bot has no answer for this.

    it also weeds out girls who have no real interest, it takes effort to answer so you find out if they are wasting your time or not.

    The positive side of it is if you get a good list you have a lot of good conversation starters.

15. Sometimes I’m expecting a reaction to what I just said or a follow up question.
    A lot my responses are outliers or definitely unexpected. It feels unnatural to move on after saying my response with a new question. Would also be weird to be like “what’s your reaction to that?”

    I think sometimes we take the back and forth expectation a little too literal. That said, yeah some are just bored or not interested.

16. As others have said, it happens to women too. Any time I have pressed on with the effort it has made no difference. I genuinely think you can tell in the first few messages whether someone is going to be worth spending a couple of hours to get to k ow better or not. But I have no idea who ends up dating these low effort people.

17. You don’t. Conversation isn’t playing 20 questions. I don’t like being asked one question after another to feign interest. What about you? And you? And then? I’m done at that point. A good way to start conversation? Humor. Talk about your day. Tell a joke. Share a story you came across. Build curiousity. When they don’t respond, carry on. Why pursue density over substance?

18. No. Never keep it going. Its not your job. These people are wasting your time.