To ask how you get more confident/skilled at flirting with men you like

[Harara]

I’m just so bloody shy with men I’m attracted to, I get very awkward and they can see the lack of confidence in my eyes and I can see them reacting negatively, even men who were initially acting like they were interested will start to back off when they see how awkward I get. I find it very disheartening, I really worry I’ll never be able to connect with someone I actually like. I’m fine with men I don’t fancy (sigh). I’m not a knockout but I’m averagely attractive and I’m intelligent and have an interesting job. I feel like I have things to offer but I just can’t get past the nerves and awkwardness with men I like. Has anyone else suffered with this and managed to improve it?

Bump

It all takes time and finding your confidence takes time. Don't be in a rush but just go out and have some fun. Make eye contact with someone and smile. I've always found that I get approached by men when I least expect it.

Is this in a particular setting? Work, in a bar?

If I were you, I'd practice flirting when out and about - eye contact, casual compliments etc. Just with random people

Ask them questions about themselves and listen raptly. Not like the stasi conducting an interrogation. I don't think you need to work on hair tossing, sparkling repartee and significant looks - just smile at them

I've always been able to flirt (well until I became old and ugly 😭).

I have very little self-confidence but flirting comes easy - it's what comes after that that isnt! For me, flirting is an enjoyable way to pass the time. It's not serious on either side, which is what makes it easy. For me it's never been about coy looks, pretending to find them fascinating etc. It's about being able to look straight at them, laughing if (and only if) something is funny, a slightly raised eyebrow if something isn't funny, a little gentle teasing if appropriate, giving as good as you get in a conversation and, probably most importantly, remembering and being able to show that you remember, something they have already told you. All of these things show that you are thinking of them as an individual who is important enough for you to enjoy spending time with. That might only be 5 minutes, but it's enough to make both of you feel good. If you're not getting interaction back, give up!

It's not serious on either side, which is what makes it easy.

Thanks for the replies. The situation I’m talking about is when I do actually like someone, and therefore it is serious for me. I agree it’s easy to be relaxed and flirt if you don’t actually like someone! I think I’m looking for tips on how I can overcome the nerves and act naturally and project confidence even when I’m not feeling confident? So that they can have a chance to actually get to know me as me and see if they like me, rather than just being put off my awkwardness? I think shyness on its own wouldn’t be so bad as men might find that endearing, but I get really awkward when I like someone - awkward body movements, unrelaxed eye contact (I think that’s the best way of putting it - I think they can see the insecurity in my eyes and it makes people back off). Awkward conversation. It’s awful to have someone approach you because they did quite like the look of you, then watch the interest die in their eyes because you’re coming off as anxious and socially inept - especially when you know you would be fine if only you didn’t like them!

I used to flirt with people I liked as well, but with no expectation of taking it further.

If somebody has already approached you, maybe try acknowledging to them that you're really bad at this, or you're a bit out of practice. They have made the first move so you don't need to worry about that.

Try not to take it too seriously- it would be lovely if something came of this first interaction but not the end of the world if it doesn't. Try to enjoy yourself. If somebody is so easily put off then maybe they're just not good enough for you? If you can act a bit more confidently that will help. This poor chap (or girl, whatever) has already shown an interest in you - if you had put yourself out there like that what sort of reaction would you like to receive? If you can manage to look straight at them and show that you are interested to then half the battle is won. A direct smile (not a mad grin!) to show your pleasure that they have come to talk to you really helps.

I feel you might do better if you got involved in some hobby or volunteering activity. That way you'd get to know each other rather than relying on first impressions. I don't think I ever flirted with my husband before we started going out together. He was the flatmate of a friend of mine and used to lure me round for dinner insisting he'd made plenty when he heard my friend on the phone to me.

The other thing is that you don't have to be witty. They're probably not sparkling conversationalists either.

One thing I did to deal with stressful situations (in my case it was public speaking) was to visualise the activity and visualise it going really well. It pretty much turned out as I visualised it. Somebody told me that really she hadn't thought I'd be so good and so relaxed doing it. I got really good feedback on it too. My previous public speaking was much less good - almost embarrassingly bad - so I think the positive visualisation - sort of like a mental movie in your mind as you imagine all the steps in the process really helped.