Scarleteen

I'll try to keep this short. Thanks in advance for listening.

Recently I started talking to this boy over Instagram. I'll call him Drew. I don't know why but something about him stood out to me. I think I developed a crush pretty fast, despite some things that I'll mention later. The reason why I like him is that he's so interesting. We can talk about anything and always keep a conversation going. We have a class together but we never get to talk in there. We've talked a couple of times, but it was always after school so it was never long. Whenever we see each other, we'll give each other this look and I think it's so cute. He always texts me good morning and good night, we flirt a little when we text, but a big thing is that he's told me a couple times that there's something he needs to tell me, but when I ask he won't say, which I find sketchy.. but anyways let's get into why I'm confused about this.
The biggest problem is the fact that Drew has cheated in the past. This was when we were freshmen. We're juniors now. This is what I'm worried about the most. I don't want to get played. I feel so stupid because I know if he ever admits that he likes me too, I would still date him. People I have talked to say "Go for him," "He's really nice," "It was a long time ago so he's probably changed." He's the first boy I have felt like this for in a while. My first ex left me damaged pretty bad and I don't want to go through that again. And if I do go for this and something does happen, I'll blame myself because I KNEW this. What if he has changed though?
Somewhat tying to the first thing, is that in the class that we have together, there's literally this girl. I'll call her Kate. Kate and Drew are friends. They sit by each other sometimes. For some reason, I'm very suspicious of their friendship. I don't know why. I never see them together outside of class. They are always by themselves, so I don't know why. But what if he texts her like he texts me? One of my friends asked me if anything's up with them. I want to ask him about it but I don't want to seem weird. Like I said, I'm just not trying to get played again.
I don't know what to do. I like Drew a lot but there are so many red flags. I mean, there's plenty of reasons also for these red flags to not even be true, It's not like he's trying to hide or anything, because we do literally talk and stuff at school, I'm pretty sure his friends know we talk but I don't want to look stupid and end up like I did with my last relationship. I already know my feelings are in too deep with this kid. What should I do?

I get that it's intimidating to do so, but I think the only person who can really tell you what Drew is feeling, if he's into you the same way you're into him, and how his attitudes and behaviors might have changed since this cheating incident you know about is Drew himself. It sounds like a bigger conversation needs to happen between you anyway; I'm not sure why he would say "I need to tell you something" and then not tell you, but that's certainly something you could follow up on and ask about.

If Drew is texting Kate as well, or has a friendship with her, I don't think that's a sign of anything sinister going on just by itself. It's not wrong or deceitful to have a texting-level friendship with a few people, even if that includes flirting; it sounds like there hasn't been any serious discussion of a relationship between you, and if he's flirting with a few people at once I absolutely get why that might not feel great to you, since you're into him, but I don't think it's necessarily a sign of a problem with how he's handling things. If you did start up a relationship and didn't want him to flirt with other people, that's something you could discuss with him, but for now it's probably not going to be really helpful or productive to you to worry too much about the particulars of his friendship with anyone else.

You say that if he liked you back you'd date him, as if it's inevitable, but it's ok to ask about the concerns you have, if you get to that point of establishing mutual interest. Do you feel like you could ask him directly about any of this?

I'd like to cover one thing that Mo didn't: it is not your job, as a girlfriend, to make sure that boyfriends or girlfriends don't cheat on you. If someone cheats on their partner, that is not on their partner for choosing to date them, or not having their passwords, or not being suspicious of their friends, or whatever else, it is entirely on them for breaking their agreement and doing something they knew their partner would not like.

Which means that in this case, if you were to date Drew, and he were to cheat on you, there would be no need to blame yourself for choosing to date him knowing about his past. You could look at it a different way and say that you did a good thing by trusting him to have learned from his past, and he is to blame for his own actions abusing that trust.

Update on this: We stopped talking. I still don't know why he stopped texting me but I thought that was weird. I would try to reach out to him but when I did he would only text back two or three times and stop replying again. Oh, and he's dating Kate now. They started getting really close after he stopped texting me. Nice. But it's okay, I got over it and I'm onto other things now. Thanks for your help though guys!

Thanks for the update!