Nobody could deny that It's gotten tougher in the age of OLD, but it's still possible to connect, and I know of quite a few women who are looking to meet people organically ( there seems to be a small renaissance of meeting people offline after many have become disillusioned with dating apps) so I think it's still worth approaching people when it feels right.

Do the preparatory work...take reasonable steps to be as good looking as you can, wear clothes that suit you, smell nice, have a fun conversation earlier to get yourself in a positive mood and so on.

Be firm but fair to yourself - you're gonna have to grab yourself by the stones and approach at some point, and it's going to make you feel a bit uncomfortable, but there's no need
to overcompensate and become a military sergeant and order yourself to approach 20 women before you're allowed to return home - that's not a high value mindset, and that attitude always bleeds through, and it's extremely off putting. No girl wants to feel like she's talking to a sex pest who's darting from one woman to the next like a dog in heat, they want to feel like they're talking to someone who's well rounded and decided to approach a girl he saw serendipitously whilst he going about his day. It's a numbers game but that doesn't mean you should just throw shit at a wall and see if any of it sticks.

The best frame to adopt I think, is of bumping into a coworker you're friends with outside of work - you just saw them that day so you're not going to make a big deal of it, and you'll speak comfortably, but not as silly as how you might be with a best friend. Basically act like you've met them before but still maintain a tiny bit of formality. Relaxed body language - not trying to look big or put on your deepest voice or any of that crap.

You don't need to jam an innuendo into every sentence - if you have strong eye contact and you seem engaged in the conversation and they find you fairly attractive that's enough, any flirting is just a bonus. Trying too hard will backfire

Do NOT approach anyone if you're in a bad mood - you will be radiating a negative energy (not in some spiritual way but in the way that it's fucking obvious when someone is in a bad mood and trying to put on a friendly face). Do something that you know will put you in a better headspace - workout, call a friend, read, listen to music, meditate, walk along the beach whatever.

Also remember that even when you're doing everything 'right' it's still got a fairly low success rate - most people have partners, many people aren't in the mood for it, some just won't like your look, some have anxiety and feel embarrassed to talk in front of others.

Approach styles

I don't like the ultra direct approach 'hi you're cute and I'd love to take you out for dinner some time' it just bleeds desperation and demonstrates that you have very low standards (for all you know she's a rude bitch with a voice like a 50 year old chain smoker). It might work for michael cera or if they find you extremely attractive but it usually seems to make people uncomfortable - I've only used it twice and regretted it.

Cold reads haven't worked too well for me either. I only do them when I'm feeling really confident (see: intoxicated) and since I have a dark and fanciful imagination I've offended a few people, and generally it's like walking along a knifes edge - even innocent things like assuming that someone's a tourist has gotten some negative responses so I tend to stay away from these in public. Things change if I'm at a friends party or some private event where we're not quite complete strangers despite having never met, and then I might say something like 'I'm guessing you've never met [the host] and just heard the beats and smelled the hot food and that's why you're keeping a low profile?'. If the opportunity for a cold read pops up naturally wherever you are then it's still worth taking - after running a quick filter to make sure it's not blatantly offensive.

I've had some luck asking women for dating advice - my best approach took place when I saw a girl reading nearby at the beach and said 'hey sorry to interrupt but can I just ask for for a ladies advice on something?' sure 'well I'm sick of doing my dating through a screen and I'm wondering how you would go about meeting people the old fashioned way? Are there any bars or events that seem to attract the right crowd that you know of?' umm... have you been to blah blah blah 'I can't say I have...I'll make a mental note of that. Everywhere I've been lately has been full of aggression and ego and it's killed the mood. Still it beats staring at pixels hoping that they actually look like the person you're meeting up with' yeah I've been there before blah blah [talk for a few more minutes and figured out I really liked her] 'anyway, I appreciate the advice, and I mean it when i say this wasn't all some elaborate pick up strategy but life's short and it would be silly of me not to ask whether you'd be interested in continuing this over a coffee sometime?' you definitely planned this, but sure I'd be up for it blah blah 'sounds good. So we can leave it up to fate to bring us together, but it might just be easier to get your number.' she gives me her number 'sorry you're not going to get catfished by a 4 foot middle aged man with one eye this time' I'll be devastated 'have a lovely day'

This approach doesn't work on all women since they need to be in the mood and they need to have a bit of time on their hands, but there are lots of benefits to it

1) You find out whether they're single right away

2) It doesn't come across as slimy and you don't need to ask for their number if you're not feeling any sort of chemistry

3) but it makes sense for you to ask them out if you've had a nice conversation

4) They might even be a wingwoman - one girl had a partner but saw that I was a decent guy and tried to set me up with one of her friends (who I wasn't interested in)

5) If nothing else you can get valuable information about the bars and clubs and events that might be worth visiting

Situational openers are still the best though - her dog comes running over to you or she reminds you of a celebrity or has a t-shirt of a band you're into or it starts pouring with rain and you both take shelter in the same area or something allows you to strike up a conversation in a way that seems organic and not as tho you're on a mission from god to get her number.

But sometimes there's nothing much going on and nothing really comes to mind, and in these times resorting to a more generic opener might be better than nothing.

General tips

Another critical thing I've learned is that sometime things will flow almost effortlessly and it's like you don't even need to think - THESE are the only interactions where you should try to take things further (or one's that are closer to being effortless than effortful). If you have an uncomfortable interaction where she seems standoffish, don't ask for the number as proof that you approached her, regardless of how attractive she is, it's a waste of time - she almost certainly isn't going to meet up with you - and it's not something that any self respecting person should do.

Let the conversation run it's natural lifespan, but wrap it up if it starts to get stale. I think the longer you talk the more rapport and comfort you can build - I don't believe in the bullshit about swooping in and getting her number in 30 seconds like mr mysterious, unless you decide to approach someone when you're in a situation where you hardly have any time to talk.

Also, instead of asking for their number, introduce the idea of meeting up again for a date and use that as the reason for getting their number - I think this seems a lot more natural and there's a better chance they'll actually be up for meeting. Always get their number not their social media too - you already know what she looks like so there's no need to try and confirm it on social media. Don't overthink when to message them - although I wouldn't let it go for more than 3 days or their memory of you might have faded and it's nearly impossible to reignite a spark once that happens.

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One area I'd like advice on is topics or questions suited to a cold approach, when things aren't really flowing effortlessly but you'd like to test the water a bit more because they seem intriguing. I don't want to start asking deep questions as though I'm on a date but I want to get them to open up a bit. So if anyone has advice here feel free to share it