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Dating : Advice for a 22 year old guy with trouble approaching women?

Dating : Advice for a 22 year old guy with trouble approaching women?


I have tried dating sites and they simply aren’t for me. I’m not horribly unattractive, but I’m not amazing looking either. I’ve got quite a few extra pounds that I’m working on. That being said, It doesn’t tend to make the greatest first impression and I am also EXTREMELY shy and stumble over my words a lot.

I would like some advice on how to approach women my age and just start a conversation. I do not want to make anyone feel uncomfortable. I am not afraid of rejection, moreso afraid of weirding someone out.

Any advice for someone who has not had good luck with dating?

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  1. One thing first: it’s impossible not to make anyone feel uncomfortable. Even if you are the most considerate person, you can’t read minds. And some women will just not feel it at all.

    That said, you can absolutely make sure the vast majority of women will be somewhat receptive. Top thing to pay attention to: smiling or at least not frowning. When you first start approaching strangers you will most likely be in a stressful situation filled with anxiety, so you might start looking intense and even hostile. Take it from someone who made that mistake for several approaches. While you are on your way to her, remind yourself to smile and make her day!

  2. Do you feel shy/stumble over words in general when you are with strangers? i.e. male or female? If so, it sounds like general social anxiety that you’ll need to work out. In that case, focus more on meeting people in general (like Meetups) to get yourself out of that. If it’s specifically when you’re in a dating situation that you go through this, then there’s really no cure aside from dating more. It’s like a muscle; you’ll need to go through it enough times that your weirding out feeling will stop appearing or you just stop caring about how the weirding out feeling may affect you.

  3. Just understand that while it isn’t like this with absolutely everyone, the expectation is still usually for the guy to initiate and make things happen, especially if he isn’t the most attractive guy. And confidence is often seen as one of the most important things for a guy to have. So if you want things to work out, you probably gotta figure out how to get over the shyness and awkwardness (those things can be issues, since apart from not necessarily being that desirable themselves, they can also give the wrong idea and make you seem like a creep)

    Some suggestions – try to make friends. Getting more experience with friendships can help with working on basic social skills. And if you get involved in various activities or volunteering or other things, you can meet people with similar interests which can help spark a connection that way. Also bear in mind that you can’t make everyone happy and will make people uncomfortable, you can take actions to limit it and keep things respectful but it is important to try and work on yourself and put yourself out there even if that makes you look like an absolute moron the first few times. Just try to learn from your mistakes, and also understand that the other person is just a person, even if they don’t like you, they aren’t going to hate you and will probably just forget you. A lot of people seem to look down on bars and clubs and stuff, but those can be good places to get some practice and get experience with meeting new people

    Also, if dating sites aren’t working out for you .. maybe you aren’t using them right and could improve what you are doing there. If you are shy and all, that could be a decent alternative or thing to do while you do other stuff too

  4. When I was younger I was super shy about talking to women. I actually ended up using a strip club to learn to talk to women. The girls are not going to reject you as they want to get a lap dance or for you to tip while they dance, which you should as that’s their job, but in the meantime I would just talk to them and see what stuff made them laugh or what stuff didn’t work. Then used those when talking to girls outside so I was more comfortable with what I was saying.

  5. If you’ve never done this before, unfortunately you’re going to have to get used to feeling weird the first few times to get good at it. It’s a hard slow burn to start off with but with each rejection you’ll get more desensitized to it and smarter about how to do it. There’s really no tricks to do it. You have to try your best at starting a conversation with something that pertains to the situation or the girl herself. A lot of times this won’t present itself to you, but when you start looking around for things to talk about they begin to stand out one by one. Just the other day I went to a bar and sat close to a girl. She happened to have her laptop on her and was looking at maps of Costa Rica so I asked if she was going there and she said yes and I talked to her about traveling because I’m about to go to Ecuador. Turns out we had some things in common because we both also visited China. This is just one example but it’s how you need to make use of whatever situation you’re in and use whatever is presented to you to break the ice.

  6. are you still in college? because in-college 22 year old women and recently-graduated 22 year old women are at slightly different stages in life.

  7. Get yourself ready for the one. Quit listening to a bunch of people who go out with tons of people. If your heart is in the right place you will have no fear.

  8. You put way too much pressure on yourself. You’re solid bro!! Just be yourself, do not rush anything and if one says no, move on:) We’re guys, rejection is a part of life. It’s a numbers game, I’m around 1/10-15. Some are less or more. Be yourself, listen, do not push and move on if it doesn’t happen. It will fucking happen! You’re solid bro!! Just be respectful but flirt!!

  9. Are you in any clubs? Have any hobbies? Involved in any games? Those are your best bets for approaching women (and I say this as a 22 year old woman).

    You are *much* more likely to have a warm reception if you are able to approach a woman with a common interest in an area where talking about that common interest makes sense – and not only that, then you’re not just shooting in the dark when it comes to finding somebody you have something in common with. You’ll know you’re starting off on a good foot.

    Personally (and of course, this is just one person’s opinion so take it however you want), I hated being approached in coffee shops and/or if I was just out on the street. I found it fairly invasive and it makes it really hard/awkward (and even borderline unsafe, considering I don’t know what the stranger talking to me is capable of or what their intentions are) to say no. Usually coffee shops are where people go to unwind/do work/meet friends, and I know I liked to do that without a stranger intruding that for me. Again, that’s just my own opinion and it may be based on my own experiences (basically being stalked when I was a barista and also observing so many other failed attempts while working at said coffee shop).

    Bars are different, because it’s a different vibe and I didn’t mind if somebody approached me to chat. People are a bit more comfortable socializing there, though it may be less likely that you’ll find somebody looking for something serious.

    My suggestions:

    – If you’re into painting, find a local paint shop that does a wine-and-paint night (this is becoming super popular), and you should be able to meet people there

    – If you’re into cooking, maybe doing a cooking class

    – Game stores often do game nights and you could participate in those

    – Also a lot of bars now do trivia nights where you can go with some friends and meet other people interested in trivia, etc

    Good luck!

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