How to flirt better

Bloomberg RealMVP
Feb 7 78 Comments

I’m a dude in my late 20s and I literally suck at flirting. I’m not good with witty puns or comebacks. I ask women ‘nice guy’ questions like what they’re doing next weekend, or if they’ve been hiking in Yellowstone or who their favorite comedian is (lol). Honestly though, women seem to love these questions and almost always respond back with an answer. But it feels one sided as in they don’t seem interested in asking questions about me at all. And after chatting this way for a week or 2, when I finally ask them out, there’s no response.

I’ve started to realize that maybe I’m doing this wrong and that dating apps are all about “game”. How do you flirt? Some example scenarios might be helpful. How do you keep her interested?

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TOP 78 Comments
  • Microsoft BarFoo
    Dick pics. Always works.
    Feb 74
    • Bloomberg RealMVP
      OP
      Oh man. Not this again *sigh*
      Feb 7
    • Microsoft BarFoo
      How to you think Bezos got Sanchez?

      :)
      Feb 7
    • Roku / Eng
      Mr.Scrooge

      RokuEng

      PRE
      Yahoo, Oath
      Mr.Scroogemore
      Bezos is small. That’s why he is scared !
      Feb 7
    • New IAmPepe
      Calm down Anthony Weiner!

      Note: he has jeans on
      Feb 7
  • TI IOlOl0
    Chatting for 2 weeks is too long. Try to get to face to face sooner. Also try to be witty on the opener
    Feb 78
    • Microsoft BarFoo
      Also try getting body to body sooner.
      Feb 7
    • Dammit not getting the joke. Could someone explain?
      Feb 7
    • Microsoft BarFoo
      “Indiana” = “In Diana”. Diana is the name of the girl he’s chatting with.
      Feb 7
    • Ha! You're right. Missed that
      Feb 7
    • Square fjfjfj
      Dad jokes, so irresistible.
      Feb 8
    • Amazon VEoy51
      This pickup line is bad and you should feel bad
      Feb 8
    • Vertivco / Eng
      FastPapuan

      VertivcoEng

      PRE
      Youtube, American Bureau of Shipping, Facebook
      FastPapuanmore
      Why is no one saying that it's bad?
      Feb 8
    • Microsoft BarFoo
      Because it’s obvious it’s bad...
      Feb 8
  • Microsoft BarFoo
    Backhanded compliments. Lower their self esteem while letting them know that you like them.
    Feb 79
    • Bloomberg RealMVP
      OP
      Huh wonder what that’s like. Care to point out a few?
      Feb 7
    • Microsoft BarFoo
      “I like girls with some meat on their bones”. Calls them fat, but says that you like them that way.

      “As long as they’re natural, I like small boobs!” Tells them they’re flat chested, but you’re cool with that.

      “I don’t go for typical Barbie types”. Tells them they’re not tall and thin and all the standard “Barbie” attributes, but you still wanna hang.

      “I like a tech nerd!” Tells then they are too nerdy for regular people but you dig it.

      Of course, the type of play you can do depends on where you are in the relationship. You can’t just intro with those lines.
      Feb 7
    • Bloomberg RealMVP
      OP
      Exactly. I feel the same. But then chatting is different. You can’t say any of this stuff 5 mins into matching with someone. Gotta learn some teasing
      Feb 7
    • Google / Eng🍑☁️
      Bad advice. This is called negging, and a lot of women will recognize that you're trying to neg them and immediately lose interest. It also makes you an asshole.
      Feb 7
    • New IAmPepe
      Stop negging
      Feb 7
    • New dluz61
      I don't know why PUAs think this is some novel trick women have never encountered before. We were all teenage girls once, and let me tell you, "negging" is just 7th grade level cattiness. You all aren't even up to what high school girls can do.
      Feb 8
    • HCL / Otherjstwrkhere
      Negging actually work, even though they know it. Because there’s truth to it. Actually you’re just bringing them down to earth nothing wrong with it
      Feb 8
    • New dluz61
      Just as an example? there was a chick in my grad program who told my friend who had just returned from her mother's funeral that she was "lucky" that she wasn't being as held to as high of standards as the rest of us, you know, because she'd been given an extension on a paper. oh, and my other favorite? same girl turned to a woman next to me at graduation and said, "oh, you're not on the honors list?" And the woman said no, and she says, "oh, I thought you were smart." Seriously, all negging is amateur hour in comparison.
      Feb 8
    • Vertivco / Eng
      FastPapuan

      VertivcoEng

      PRE
      Youtube, American Bureau of Shipping, Facebook
      FastPapuanmore
      Compared to what? What lines would be better?
      Feb 9
  • eBay OG 💎
    Make fun of girls in a nice way without hurting them.
    Feb 76
    • Bloomberg RealMVP
      OP
      Yeah this almost always gets me blocked
      Feb 7
    • New mdGG61
      Lol you guys are such losers... make fun of yourselves instead. Self deprecating jokes.
      Feb 7
    • Microsoft BarFoo
      mdGG61 is right. Girls love a guy who can make fun of himself. As long as it’s always along with a laugh and not *all* the time. And when she compliments you, don’t turn it into self-deprecation, because that shows her you actually don’t think well of yourself.
      Feb 7
    • New mdGG61
      Feb 7
    • eBay OG 💎
      That’s okay OP there will be some girls who will get pissed or block you, just ignore them like we are ignoring mdGC61
      Feb 8
    • Vertivco / Eng
      FastPapuan

      VertivcoEng

      PRE
      Youtube, American Bureau of Shipping, Facebook
      FastPapuanmore
      Doesn't work more than 20% of the time.
      Feb 8
  • Google / Eng🍑☁️
    2 weeks is way too long. Within a few days of first starting to talk, you should have already scheduled a date.

    Other than that, it doesn't sound like you're doing anything wrong.

    Also, I used to make the mistake of treating "agreeing to meet" as the end goal, so I didn't make an effort to talk to people in between scheduling a date and actually meeting with them. Don't be like me; keep flirting up until you actually go on the date. It will make the date itself go better.

    Ignore any advice about teasing unless you're already the sort of person who teases your friends and they respond positively to it. Teasing can work, but if you execute it clumsily, you will come across as an asshole, so it's a risky move if you're not a teasing sort of person in general.
    Feb 72
    • New dluz61
      ^^ great advice here
      Feb 7
    • Intel :
      I wouldn’t recommend scheduling a date far in advance...up to 2 days is ok
      Feb 7
  • New -joker-
    It's surprising. I try to find 'nice guys' on dating apps, someone who talks decent things and builds a connection rather than jumping into the flirting/sex shit. But I don't find many.

    You aren't doing anything wrong imo. But just try to meet earlier. Women get more attention on dating apps than you can imagine, so if you don't talk for a few days, she has already forgotten about you. Try to meet as soon as possible, and keep the conversations going.
    Feb 70
  • Amazon jefe_bezos
    Pretend like you are teasing your little sister in a playful way. Don’t neg too hard where they’ll get pissed off, but don’t be a thirsty hoe either.
    Feb 70
  • New mdGG61
    Op how much would you pay for a service where you upload the conversation you're having and a girl would point out exactly where you fucked up and why? $50/hour?
    Feb 77
    • Bloomberg RealMVP
      OP
      What about a limited trial?
      Feb 7
    • New mdGG61
      Sure but I need to know what the market will bear to measure viability.
      Feb 7
    • Intel :
      Or better yet she suggests responses to a conversation you’re having with another girl
      Feb 7
    • New mdGG61
      That could be a feature too, but if you get people to do the work while texting, are you going to get an actor for the in person meeting?
      Feb 7
    • Intel :
      I don’t have the issue myself, but generally flirting/playful teasing etc is taken much better in person (context added, can’t get unmatched)
      Feb 8
    • Intel :
      Also for clueless guys, being told what messages would not go over well before sending them would help. I don’t mean that someone else should come up with all the responses - more serve as moderator
      Feb 8
    • New mdGG61
      "Tinder texting moderator for clueless guys" sounds like a legit startup idea.
      Feb 8
  • New IAmPepe
    Just imitate our lord and savior Bezos
    Feb 74
    • New / Eng
      罪人

      NewEng

      BIO
      I hate these niggas more than the Nazis.
      罪人more
      He’s a satanist.
      Feb 8
    • Microsoft BarFoo
      He should say he’ll show her with his eye.
      Feb 8
    • Dropbox / Eng100k🔗🐼
      What does that even mean, to love someone alive, vs dead?
      Feb 8
    • Walmart.com fiVn5$!Br
      This only works if you’re a billionaire 🤑
      Feb 9
  • Bloomberg i485
    buddy I used to have the same problem like you.

    Then I figured out girls get turned off when I say I work for Bloomberg coz girls get turned off by Fortran. Since I started saying I work for G I've been drowning in pussays and never look back.
    Feb 81
    • Google danbb
      “Girls get turned off by Fortran” 🤣🤣🤣🤣 god bless you
      Feb 8
  • New / EngXorgatron
    Two weeks is too long to be chatting on a dating app - as a woman I can usually tell if the man sounds interesting within the first day or two (sometimes sooner, but I like to give it a bit of time just to make sure there's time to spot any really obvious red flags). I tend to be picky with matches so when I do match with someone there's already a higher chance of them standing out as an interesting person, and I'm pretty sure many women tend to be the same - screening early. The point is chatting for two weeks can wear out the interest sometimes, and then if you do see each other you'll have already covered a lot of basic conversation points that you could've used in person.

    I'd suggest giving chatting just enough time to make sure you're interested and then suggesting to meet somewhere public (eg casual coffee date) ASAP, maybe within the next couple of days. Also, don't be afraid to joke around and let your humor show in chat or in person. Don't be an asshole but don't tiptoe trying to seem like an overly agreeable person either - we appreciate men who can own their humor (you'll have to gauge how far you can go with each person of course)

    I'm not sure what dating apps you're using, but personally I haven't been a fan of tinder. Maybe it's different for men. When I was more active on dating apps (for a few weeks, but enough to meet a few interesting people) I preferred less "churny" seeming apps like Bumble or Okcupid. One benefit of bumble is also that the woman has to message you first, so you sort of guarantee some level of initial tiny investment. Plus if she's not boring she'll send a good conversation opener for you to bounce off of.
    Feb 80
  • Dropbox / Eng100k🔗🐼
    1-2 weeks is way too long to chat. If he doesn’t ask me to meet up by a week I assume he’s not interested and I move on.
    Feb 80
  • New @(^_^)@
    D.E.N.N.I.S. system.
    Feb 80
  • Quanergy Systems xKLr07
    talk about your ex
    Feb 70
  • Red Hat / Product
    Abe_Fr0man

    Red HatProduct

    BIO
    I have the innernets
    Abe_Fr0manmore
    Be confident.
    Smile.
    Make her laugh.
    Feb 70
  • EMC yskV77
    Just be yourself! Maybe it’s the way your asking them out? You could try phrase as more of meeting face to face than going out, that way if there is chemistry there you’ll know.

    I feel like meeting people in person is easier because you can more easily gauge if you like each other.
    Feb 70
  • Quanergy Systems sj5uq
    It's much easier after you've been married for 10 years.
    Feb 94
    • Amazon babymakes5
      LOL. Flirting when you’re married is definitely much easier. You share rituals and inside jokes and other things that get you in a playful mood.
      Feb 9
    • Quanergy Systems sj5uq
      i wasn't taking about flirting with my spouse
      Feb 9
    • Amazon babymakes5
      You mean flirting with other people?
      Feb 9
    • Quanergy Systems sj5uq
      you Amazonians are sharp!
      Feb 9
  • Amazon babymakes5
    OP, flirting is a game. It’s cat and mouse, where a woman wants to be pursued but not too much (desperation), and not too little (she wants to be desired and pursued).

    Flirting is a way of figuring out if you are compatible in a playful, light, low-risk way. Once you know you like her, ask her out. What probably happened is that she misinterpreted your interactions as “friend zoning” her.

    Years ago, when I was single, I spent 2 days contemplating whether to ask a girl out (my now-wife). Someone told me I was an idiot for waiting too long - and that if I didn’t ask her out as soon as I knew I wanted to, someone else might beat me to it.

    So, my suggestion for you is keep doing what you’re doing but on an abbreviated time frame. If you like her, ask her out with something like “Why don’t we meet in person so we can get to know each other better?” And then suggest an activity conducive to that.

    Good luck, OP. I hope this helps.
    Feb 92
    • Bloomberg i485
      don't you get your marriage arranged?
      Feb 10
    • Amazon babymakes5
      Nope. I met my wife the old fashioned way, before apps and when online dating was still pretty new.
      Feb 10
  • VMware / Eng
    PJLD43

    VMwareEng

    BIO
    Sr MTS.
    PJLD43more
    If you can understand Hindi this is totally a shitty video. The whole story and the attempt by the guy to convince us that this story is puke-able. However the way he flirts with the girl was truly a lesson for me. Each girl is different. But I found the tone and the emotion he developed to flirt was appropriate. Maybe this will help you. Dig through the part 3 and part 4. https://youtu.be/mFgsnkdCYfk
    Feb 72
    • Vertivco / Eng
      FastPapuan

      VertivcoEng

      PRE
      Youtube, American Bureau of Shipping, Facebook
      FastPapuanmore
      Helpful, but not helpful enough. Not all your brothers understand Hindi or Urdu or Cantonese.
      Feb 8
    • VMware / Eng
      PJLD43

      VMwareEng

      BIO
      Sr MTS.
      PJLD43more
      That's why it starts with an if condition. It means Skip the answer if you don't
      Feb 8
  • Dropbox IGCk17
    Practice. It's a skill just like anything else my guy
    Feb 91
    • Vertivco / Eng
      FastPapuan

      VertivcoEng

      PRE
      Youtube, American Bureau of Shipping, Facebook
      FastPapuanmore
      That's some of the worst advice ever given. This person is already practicing.
      Feb 9
  • VMware codejunkie
    Texting for 2 weeks is way too much.
    Ask the girl to meet up within 5-10 texts and save these questions for when you meet up.
    Feb 100
  • Intel Pajajsj
    I hope you mean you figuratively suck at flirting.
    Feb 80
  • New / Eng
    罪人

    NewEng

    BIO
    I hate these niggas more than the Nazis.
    罪人more
    Stop worshipping women. The more respect you give, the more you will be seen as passive, not dominant. If you are seen as weak and/or passive, then you are classified as a woman in her mind.
    Feb 80
  • ViaSat / Designmark1650
    Check out Adrian Gee on Youtube
    Feb 80
  • Microsoft slamet
    Its always abt you asking questions at first. Ask her a ton of questions and build on her answers. Ppl always like talking abt themselves.
    Try to find common traits, likes and dislikes.
    Throw in a few compliments here and there. Build that intimacy.
    Once she starts asking questions and sends emoticons, you are golden!

    Also, if you get to a point where you guys are almost planning a date, say all the nice things you would do on a date and have her fantasize that experience.
    Feb 70
  • Google rEff50
    Friendly but not mean spirited teasing. A good mindset to assume is that you are 10 and she is the friend of your little sister.
    Feb 70
  • Airbnb Kgtn
    Look up Todd v dating on YouTube
    Feb 70
  • Microsoft UG8Dd3
    There are books and videos to help
    Feb 70

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