I’m (18M) in love with a shy girl (17F) who I dated for a very short amount of time before and I need to know if I should try again or move on.
Let me provide some background information. There’s this shy girl that I’ve known since middle school and really started to get to know in high school because we’re both in theatre. We’re both seniors now and I wanted to confess my love to her, so I did over Instagram DMs (I didn’t want to ask her in person out of consideration for her feelings). She said that she replied with the following: “Hey, so I’ve never gone out with anyone before and I’ve never really liked anyone like that before, but you’re a pretty cool guy and we get along quite well. I need you to know that if I went out with you, I’d be testing the waters with the whole going out with someone thing and I don’t want you to feel like I’m using you as an excuse to decide whether or not I would actually want to try dating. It’s difficult to explain over text without writing a whole essay, but long story short some part of me wants to explore something akin to a romantic relationship while at the same time part of me wants ...