How to get started with dating?

[flaxcapacitor]

Hi. I wanted to made this as straightforward as possible (and resist my adhd urge to fill it with details that may or may not be relevant and procrastinate then never post it).

How does a person who doesn't know the first thing about flirting and dating get started?

I'd love to just be able to flirt with a woman I like, see she's flirting back and then ask her out but I've never been able to.

I'm 42 and have been single almost my entire life. I did have a brief relationship in my 20s but I was sort of manipulated into it and she just wanted to use me to get a free holiday, so I've still never asked a girl out or had a girl be genuinely interested in me. I honestly find this quite depressing and feel lonely, starved of intimacy and undesirable.

I do approach women and can be sociable and outgoing so the issue isn't that I'm just not meeting women but I never see any indication that I should ask her out, I flirt but only get platonic vibes back and I don't want to be that guy who asks out women when it's obvious they don't want to be asked out.

It's not easy to talk about either. Especially since the rise of a certain online cult of misogyny, I don't feel I can expect the benefit of the doubt that I'm not one when I'm a single guy complaining about being single, so rather than spend paragraphs talking about myself I'll just leave things there and ask, could I be missing something? Can I be more desirable? Am I wasting my time and some people just don't have what it takes to find love.

 

Thanks

[Gebidozo]

I don’t think you should wait for some special non-platonic vibes to ask a woman out.

Most of the time the first date is still platonic anyway, i.e. it’s just a meeting of two people figuring out whether they have chemistry or not.

If women continuously reject you as a romantic prospect after one or two or three dates, then yes, we’d have to discuss the possibility of something you say or do that repels them.

But this hasn’t happened yet, so be brave and just keep asking women out on dates. Then see what happens.

[Foxhall]

On 8/14/2025 at 12:10 PM, flaxcapacitor said:

How does a person who doesn't know the first thing about flirting and dating get started?

I think a starting point is being more sure of yourself or at least faking that ,

women tend to like a certain confidence or at least a guy who clearly knows what he is about or what he wants,

I think if you carry that air about your chances of randomly meeting someone increases significantly,

life gives us all chances - Ive had plenty - with women yes definitely a few- Ive tended to blow those chances- but nonetheless ,I think not to withdraw subconsciously is also important-keep striving to function well on a daily basis and the connections will happen when the time is right.