hi!
about 14 months ago i met this amazing beautiful girl on Her and i’ve had a crush on her most of the time we’ve been friends. it’s the longest i’ve ever waited to go on a first date. over time we gradually became a lot closer, from talking and hanging out every once in a while to weekly sleepovers and daily text conversations. but nothing physical has ever occurred other than good hugs.

she’s supported me so, SO much in the last several months. i’ve had a lot of traumatic experiences this year and she’s been there for me every step of the way, and i will forever appreciate that. i really, really want to treat her right. she’s never dated anyone before, which is shocking because genuinely she’s so so pretty and intelligent, but she’s reserved and a lesbian. i’m bisexual, so i had more options in the past and am less reserved so have dated a few people in the past, men and women.

both of our favorite holidays are halloween, so we made plans to see a spooky movie. afterwards i gave her a gift (a coffin resin container, a matching ghost keychain, and a custom CD amongst other things) and finally worked up the courage to tell her how i feel. i asked her if she wanted to go on a date with me, and she said yes!!! i’m so excited, but very nervous. i’m honestly so head over heels for this girl and i’m soo scared of messing things up.

i’m very anxious about ruining our friendship but i’ve gotten a lot of green flags from her and i really think she likes me too. but i haven’t done this in a while (haven’t been on a date with another girl in at least 4 years) and i’m afraid i’m rusty, and i don’t know how to flirt well.

i planned a big day: museum, cooking, painting pumpkins, and watching the sunset at the top of my town. all things we both enjoy doing. i think it will be good, but i’m nervous that it’s too much. does that sound overwhelming?

any first date advice? or specifically advice on dating a friend? because we’ve known each other for quite a while now i feel like the usual first date tips don’t quite apply. especially because this is her first first date, i really want to make it special. what should i do?

2 comments
  1. Well, that’s exciting.

    Sounds like you have a lovely time planned for each-other.

    I know you’re nervous, but don’t be.

    Things might feel a little different because you’re on a ‘defined’ date now…. But you two got along amazingly as friends right?… Keep that friendly chemistry up.

    Don’t need to go into full date mode, can do something simple to make it feel like a date by holding hands and flirting.

    You two are both excited for the date… Things will turn out just fine.

    I am sure you both will have a good time.

    Just try to avoid shutting down like you don’t know how to act around her… You *do* know how to act around her… You’ve been friends, keep that comfort level between you two up and ride on that train… And add subtle layer like holding hands or a peck on the cheek. Baby steps.

    Things will work out.

  2. Hey congrats on asking her out on a date. This person sounds really important to you, I can only imagine how helpful they were through that earlier rough time.

    It’s okay and even healthy to be a little nervous about you first date. You’re doing exactly what you need to be doing. You’ve picked activities you know you both enjoy, and they allow you both to share an experience while having as much conversation as you want. Just being able to spend time together sharing each other’s company in a way where you both feel supported, accepted, and seen/heard is 95% of a first date. Genuine fun on a date is really built on that foundational stuff, and you’ve got a great start.

    I’ll only recommend two things to keep in mind that made all the difference when I asked my best friend out (we eventually married):

    1. It’s okay if date plans don’t go 100% according to plan. People bond over bumps in the road, so don’t feel too much pressure to make everything go perfect. This person already knows you on a deeper level than most and and really likes you anyway. Lean into that bond when you start to question yourself.

    2. Don’t be too afraid to open up a little around expressing affection when the moments feel right. It can be as simple as, “I really like spending time with you”. It’s just a small signal and a tell that you’re emotionally available, and it gently tests and nudges how far you both can start to step a little out of just-friends territory and into romance territory without it feeling rushed, weird, or pressured. As long as you’re communicating honestly, clearly, and respecting each other’s boundaries, you’ll always have the foundation of your friendship to work with and build on.

    Best of luck OP.

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