I’d lean into being honest. Don’t get so caught up in your own head that you start using the date like free therapy but, like, I’ve found that disarming honesty is a good way to connect with others and to help ease the tension and stuff.

It requires at least some self-restraint, at least for me because I’m a chronic overthinker (I’m not sure if that’s something people here would have noticed yet /s)

Self-pity is not really endearing so try not to veer into that but if I were in your shoes and he asked me “How are you?” I’d probably chuckle and say “I’m incredibly nervous” but in a playful way - not in a boohoo-poor-me 😭😭 way but just naming the elephant in the room and being playful about it.

It might be that I come from a culture that values banter but the ability to joke about things and to be very incisive with your honesty here is valued quite highly.

Chances are that he’s gonna be feeling nervous himself and if you say that you’re feeling nervous then it’s going to give him the chance to breathe out and be like “Yuuup, me too haha”

I think in some ways it signals that you are a good communicator and you’re able to talk about the difficult topics and you’re capable of dealing with tricky emotions with a degree of tact etc. I guess for some people they look for suaveness and someone who is effortlessly confident. I don’t have those things so I play to my own strengths but also I try to attract in the people who vibe with the kind of person I am.

You might have the urge to use a lot of praise but I’d say be reserved in how much you give. Not in a treat-em-mean-keep-em-keen way but just in the sense that being too effusive with praise can feel like flattery and it can, ironically, create a distance with the other person because it might seem a bit desperate or over the top. Praise should feel earned by the other person and it should feel like it’s coming from someone who genuinely knows them or otherwise it can feel uncomfortably like worship. With that in mind, qualifying statements are your friend when giving compliments at this stage: “You seem like such a sweet person” is good whereas just straight up saying “You are such a sweet person” might feel on the receiving end as being a little like “But hang on, you barely even know me…”

I often tend to compliment behaviours over the person until I feel there’s enough connection and I know enough of the person to praise who they are directly, so that would look like saying “Oh my God, that’s so sweet!” instead of saying you are.

But I come from a low-praise culture where people take a long time to warm up to others so that might not be applicable to your situation.

Try to be an accurate representation of yourself but put your best foot forward and try to keep the less flattering things about yourself a bit tucked away until there’s enough mutual connection that you can let him in to witness some of your deeper flaws and anxieties.

Don’t force things. He might not be attracted to you that way or he might not vibe with you and that’s okay. Don’t try and change yourself into someone you are not just to get other people’s approval or affection, that inevitably leads to disaster. You should do this with the hope that he will like you for who you are.

You got this. Congrats!