That title was confusing, sorry lol.

Okay here’s some background info

I’m 23 M, she’s 23 F. Our moms are best friends, we’ve grown up together, went to the same church, church schools, and even high school together. We live about 15 min apart. We both graduated from college last year, she went to a local one and I went to one on the other side of the country. Both of us have been single most of our lives, except 3 years ago for me I had a girlfriend for half a year, and I think last year this girl had a boyfriend but it only lasted maybe a month. We are both very shy, quiet people.

I have had a crush on her as far back as I can remember, pretty much since the day I met her when we were little kids. Because we’re both pretty shy though, that lead to us barely ever talking or hanging out at all really. The only times I’d ever see her is at family gatherings since our parents are friends and all.

Since I’ve grown up, I’ve learned to be a bit more outgoing, realized that you only live once, etc. and I’ve been giving this whole situation a lot more thought.

I dont even know if we really would be good together, but I’ve tried to get over her plenty of times and focus on finding someone else, yet I keeo circling back to the “what if” with her. What if she does like me, what if we would be good together.

Over the past few years or so, I’ve been sending her innocent small-talk texts, snaps, replying to her Instagram stories etc. just trying to engage in any sort of conversation. To the very general snapchats (like if i just took a picture of my pool or something with no caption or anything) she would just open it and not respond. I kind of expect that though because that’s not really me putting much effort into a convo, so she probably assumes I send that same snap to everyone. When I send more direct things like “hey whats up” or reply to her stories and such, she always responds and always does so in a very friendly way. The problem is, our convos never go anywhere. Ever. Like they always just stay small talk, innocent, and only a few messages back and forth.

So about half a year ago I decided to ask her if she’d want to go to the local fair with me that upcoming weekend. I was super nervous to ask but my friends gave me the push I needed so I did it. She ended up replying basically saying that she would love to but she can’t that weekend. No reason why, just that she’s “busy”. I took that pretty harshly and felt super down about it all, figured she just really isn’t into me at all.

Time passed and I got over it, and my friends started to tell me “maybe she just got nervous since you sort of asked out of nowhere to go on a date with her basically, so she freaked out and said that excuse, not because she isn’t interested but because she didn’t know how else to respond”. This is possible. Who knows. It kind of makes sense though.

So fast forward to a few days ago, we’re having another small talk conversation as usual. She’s away for the weekend (this past weekend) so I say, “when are you getting back?” and she replies, “I’m leaving here tomorrow night!”. So I say “well when you get back, we should go get some ice cream or something!”. I was so scared to send that text. She replied, “Yes for sure!”.

That was that. Did I just basically ask her out on a date? And she said yes?

Nahh too good to be true. Either she misunderstood me and thought I meant to go with like friends/family, or she just said yes to be nice but will make up an excuse as to why she can’t go when the time comes.

That was 2 or 3 days ago. She’s home now.

I just today found out that, this upcoming weekend, our families (and some other families) are having a get-together BBQ.

Do I text her asking if she wants to go get ice cream this week?

Do I hold off on it until after the family party that ill see her at?

Do I just give up?

Do I pretend nothing is going on at the party?

Do I ask her at the party to go next week with me?

I just need some advice please, anything helps 🙂 Feel free to ask any follow up questions you might have

TL;DR im scared to make any moves with my lifelong crush, I have an opportunity to this week, but im afraid it’s a bad idea