I might come back and write a longer reply when I'm not on my phone. Edit: lol this got real long. Let me try to be helpful with this tiny keyboard in the meantime.

I would usually chat for maybe 2-3 days, and I think the longest chat I’ve had active was for a week

That is too long to be chatting! When I first started dating I would also talk to people over messages for a long time, and also I got no dates. Then one of my friends was like "I just ask 'em out. What are they going to do, say no?" That'd be doing you a favor because you can move on.

The problem is I’m not really good at chatting Relatable. Most of us aren't naturally good at it. But the good news is the bar for acceptable is pretty low, and you can get better with practice

(it just feels so fake asking the same old small talk stuff, like you know, how you feel inside when put on a fake smile?)

What sort of topics are you chatting about? In my head there's like a rough hierarchy of quality topics

Best : something explicitly on their profile you're interested in. You can usually assume if someone wrote "I love NK jemisen's books" they will be happy to talk about that. Remember to try to ask open ended questions!

Okay: something implicitly on their profile you're interested in, like if they live in a neighborhood you like, if they have a job title you can relate to.

Bad: generics like weekend or holiday plans. Think hard before using this.

Unacceptable: anything about their body. Anything solely about you. Copy-pasted messages.

Embarrassingly bad: "hey". Do not under any circumstances send a dead end message like "hey". You open with a hook or you don't open.

For example, I matched with a woman whose profile said something like "tell me about cool [music] shows!". We matched, I wrote something like "hello! There's this amazing band Screaming Females playing Thursday. You ever listen to them? I saw the singer crowd surf while playing a solo once!". She wrote back that that sounded amazing. We talked a bit more (the details escape me and I can't find the original conversation now, a year later), and within the hour I asked if she wanted to meet up for a drink. She said yes. We had a great time.

Side note: probably don't do a first date at a concert. You need to be able to talk to your date, and also bail early if it's terrible!

and I don’t know how to organically switch from a random small talk to asking them out.

This used to give me a lot of trouble, too. In my experience you don't really have to be very organic about it , really.

It's like:

• your initial message
• their good response
• your follow up
• their good response
• explicit check for deal breakers
• your "amazing. Do you want to go out for a drink and see if we get along?"

The last two can feel a little weird, but you really need to get to an in person date if you want to have any luck.

Whats your criteria for this? What’s a good number of exchanges, and do you ask your dealbreaker / serious questions during this time, or just keep it all casual, like asking them about their interests etc?

I don't have a firm rule but I feel like two or three quality messages are enough. If I'm getting dead end replies (where they respond but don't ask anything) I might fish a little longer if they're really hot or something. Try not to let the conversation roll into another day.

Side note: I highly recommend the rule of three. Don't send three messages in a row. You can send one message. If you don't hear anything, you can send a second. Under no circumstances should you send a third message in a row. Working backwards from that, make your second message good. Don't blow it on "hey wyd?".

I also have a pretty big potential deal breaker about myself. It's listed explicitly on my profile, but a lot of people don't read profiles. I ask before asking them out. Usually with something like "Before we get too invested, did you see the thing in my blurb about {deal breaker}? Is that something you're comfortable with?"

Some people bail at that point. But that's fine. If people respond positively, that's a great time to ask them out.

But many people don't! If they're cool with it, I ask them out. Suggest a date and location and see what they say.

Once plans are made, I generally do not keep texting. The more you text before meeting, the more likely you are to say something that doesn't land right. People are fickle. In person you have body language doing you a lot of favors.

I do text the day before to confirm they're still up for it, and then when I leave the house to head to the date, but that honestly might be a bit much. I'm just really burned by being ghosted or dealing with poor communicators, I over communicate a little myself.

Unrelated tip: have some date plans ready to go. I've got a handful of local bars (walking distance from my home :finger guns:), a couple places in a more central location, two non alcoholic ideas

Ok I should get back to work. Hope this helped someone! Feel free to ask more.

Glad to hear it worked out for you, that's awesome!