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 nothing to do with it. That being said, if you would still like to, then yes I would like to go out with you. We can talk tomorrow if you’re confused about all that.”

Luckily I did understand her because I’m not too well versed in the dating landscape either. We met up the next morning at school and talked about us dating. We seemed to enjoy our own company for the time, then we had to go to our different classes. We have the same class at the end of the day, but we didn’t really talk to each other that much in that class. Later that night, she texted me the following:

“I didn’t get to talk to you before you left, but I’ve been thinking about this whole situation and I realized that I don’t think this is going to work. I think you’re a great guy, and I’d love to still be your friend, but just the thought of going out with anyone gives me a lot of anxiety. I appreciate you asking and I really appreciate the way you choose to ask me, but I don’t want to be in a relationship with you if I know I can’t reciprocate you’re feelings towards me. I’m really really really sorry, and I feel terrible about going back on my word, but I don’t think I can do it.”

So we broke up after less than a day. I reassured her that I would like to date her, but if dating me makes her so anxious, then I am fine with not dating her for her own health.

The following weeks were a little awkward, but things eventually went back to normal. She invited me and a bunch of other theatre people to a Halloween party at her house, and me and her parents happened to really hit it off (her dad happened to used to have the same exact model of truck, 2004 Toyota Tacoma 4-door, as me when he was younger). Her dad and I still talk a lot about my jobs and my future plans and he talks about things like how his land was used in Ron Howard’s film “Hillbilly Elegy,” which is pretty impressive.

A week ago, after one of our school’s theatre performances, our theatre troupe went to Applebee’s a group of us sat in one booth and me and her happened to be sitting directly across from each other in the booth. We all talked as a group mostly, but when me and her talked to each other, she was so nice to talk to and I think she thought the same based on how she talked to me.

It’s been a about 2 months now since we first dated, and I think my love for her has sparked once again. I want to ask her out again, but I’m not sure if I should. Our friendship isn’t awkward anymore and I fear that if I ask her out again, then things will get even more awkward than last time.

Should I try again, or move on and forget about dating her ever again?

Submitted November 12, 2021 at 01:09AM

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 nothing to do with it. That being said, if you would still like to, then yes I would like to go out with you. We can talk tomorrow if you’re confused about all that.”Luckily I did understand her because I’m not too well versed in the dating landscape either. We met up the next morning at school and talked about us dating. We seemed to enjoy our own company for the time, then we had to go to our different classes. We have the same class at the end of the day, but we didn’t really talk to each other that much in that class. Later that night, she texted me the following:“I didn’t get to talk to you before you left, but I’ve been thinking about this whole situation and I realized that I don’t think this is going to work. I think you’re a great guy, and I’d love to still be your friend, but just the thought of going out with anyone gives me a lot of anxiety. I appreciate you asking and I really appreciate the way you choose to ask me, but I don’t want to be in a relationship with you if I know I can’t reciprocate you’re feelings towards me. I’m really really really sorry, and I feel terrible about going back on my word, but I don’t think I can do it.”So we broke up after less than a day. I reassured her that I would like to date her, but if dating me makes her so anxious, then I am fine with not dating her for her own health.The following weeks were a little awkward, but things eventually went back to normal. She invited me and a bunch of other theatre people to a Halloween party at her house, and me and her parents happened to really hit it off (her dad happened to used to have the same exact model of truck, 2004 Toyota Tacoma 4-door, as me when he was younger). Her dad and I still talk a lot about my jobs and my future plans and he talks about things like how his land was used in Ron Howard’s film “Hillbilly Elegy,” which is pretty impressive.A week ago, after one of our school’s theatre performances, our theatre troupe went to Applebee’s a group of us sat in one booth and me and her happened to be sitting directly across from each other in the booth. We all talked as a group mostly, but when me and her talked to each other, she was so nice to talk to and I think she thought the same based on how she talked to me.It’s been a about 2 months now since we first dated, and I think my love for her has sparked once again. I want to ask her out again, but I’m not sure if I should. Our friendship isn’t awkward anymore and I fear that if I ask her out again, then things will get even more awkward than last time.Should I try again, or move on and forget about dating her ever again?