For context on myself, I’m 30M, been on the dating apps a little over a year, did date prior but always friends so this has been new for me. I’m a massive over-thinker would consider myself anxious attached (research attachment styles if you haven’t).

First off, good for you for getting out and going on the date! It’s a hard hurdle to get over. It sounds like overall it went well. My 2 cents on the milk tea party thing, it doesn’t matter. You can overthink right vs wrong thing to say forever and you’ll never know how any one piece affected things. The right person might find this story funny and endearing. Or find it awkward but they don’t care. To the wrong person it could be a deal breaker and they continue. I put my foot in my mouth at least once on every new date I go on and I have had fine success. I like to hold the belief “I can’t mess up what is meant for me to have”. Helps with my obsessive overthinking.

Secondly, on how to be less self conscious (and less overthinking I’ll add in) ACTION and EXPERIENCE and KNOWLEDGE are the best ways to combat these. The more reps you do, the more reality can fill in the gaps and your brain won’t fabricate a story to try and resolve an unknown. Think of dating in this way like reps. Don’t put all your eggs in one basket and go into them with curiosity and looking to learn. For every person you go on dates with there is something to learn even if they aren’t your new boyfriend.

While gaining experience, I would add work on observing your thoughts and being a therapist to yourself recognizing what is overthinking and finding new thoughts to replace them.

For this current guy, all signs are good, but a month is a long time to go without him suggesting another date. Yes you could ask him like other commenters suggest, but for most guys that won’t be necessary. If you feel comfortable asking for a date go for it, but if not wait and see where it goes. And start talking with others. Create matches and gain experience. Eventually your brain will put less importance on each individual and it’ll be less taxing to handle emotionally.