How / when should I tell my friend I'm in love with / want to date her?

[Estobawk]

So I think I had my first crush on a girl ever maybe 4 months ago, but I also came to really want to be her friend, not necessarily in any romantic way. A bit over a month ago, I finally started a conversation with her and we've become friends, Sometimes we talk on the way home from school. I really want to tell her about my crush, but I guess I'm just worried about overwhelming her.
But recently I've felt a lot more compelled to tell her, as the school year is winding to a close, but she has also been a lot more friendly to me. She thanked me for starting our friendship, and that I've helped her to enjoy school a bit better, and other nice things in an email convo. I've just been constantly looking over those messages getting the warm fuzzy feelings, but I can't tell if and how I should confess that I like her.

[Sam W]

Hi Estobawk,

A big positive of telling someone you're crushing on that you like them is that it let's you know if they share that interest, or if they're open to dating you! But, as you've pointed out, both sides of that conversation can feel pretty overwhelming sometimes.

One thing I encourage people to consider when they're wanting to confess a crush is if they feel ready/have a plan for what they'll do for the various likely outcomes, including rejection. Do you feel like you're at that point?

[Estobawk]

I feel like I've been thinking about that kind of thing for a while, but I'm not sure exactly what I'd do. What even are the likely outcomes? Where and how would I tell her? I guess the best answer I have for "do you feel like you're at that point" is that I think I could be... soon?

[Sam W]

Okay, we can work with that!

Let's star with the outcomes and keep it simple by saying she'll either say "yes" to being asked out or "no." It can really help to have a plan for what happens if she says no that includes things like how you'll take care of yourself that day if the rejection ends up hurting. Does that make sense?

As for when and how to do it, I really like the advice given here for how to ask someone out: https://www.scarleteen.com/article/advi ... _a_guy_out

[Estobawk]

Yes, I think I understand. I think I already know a lot of this advice in the back of my mind, I'm just not confident in it because, obviously, I've never done it before! I usually like to talk to people to get advice more yup help solidify that and give me some specific ideas.

[Emily N]

It’s brave to do something that is both emotionally vulnerable and something you’ve never done before! And it makes sense to get advice from others when doing something new, it definitely helps me with my confidence. And there’s no rush to proclaim your feelings if that’s what you decide, the nice thing is you get to work on your own timeline. You mentioned you are nervous about overwhelming her if you tell her about your feelings - do you want to talk more about that? Are there other specific questions you have?

[Estobawk]

I'm not quite sure how to word why I feel that way. I was in "special education" for like 5 or 6 years, and only this year have I gone to a respectable school, so in a year I've had to grow up A LOT. I've never had good friends just because of the situation, so when I'm not depressed for the first time in so long and also at the age when I start having very strong feelings about other people, I guess I really, really want to have a close relationship, so maybe that might explain a bit why I want to tell her so much.
As for other questions, I guess I'm wondering if you had any advice regarding maybe how I could maybe... subtly queue her in that I'm interested in her but in such a way that it wouldn't be too much or feel like it's gone too quickly once I tell her.

[Carly]

Hey Estobawk -- Though I totally understand not wanting to come on too strong, I also think trying to be subtle is a little risky too. You could accidently miscommunicate if the hint you're dropping has a different meaning for her, for example. I would recommend trying to find a way to be as straight forward as possible, even if it moves slowly. Puppy Love: The Do's & Don'ts of Crushes is all about navigating this. This guide from Sex Etc. might also be helpful to you. Does anything feel helpful from these? Any approaches that you think you could be comfortable trying?

Also, I just wanted to say quickly that the school or program you were in before is in no way less respectable than where you are now. Our culture teaches us to view those who need additional or specialized education or accommodations as inferior to those who don't use them, but that is simply not true. We can talk more about this if you like.

[Estobawk]

I guess what I'm asking is, how can I be saying "I like you" both in subtlety and overtly. I want to tell her my feelings, but how do I, before and after that, keep that going, but not overload things, or make her feel like the only thing I care about is our relationship? I keep thinking about just up front telling her that "I'm into you, and I want to see if we could take a relationship somewhere," but I'm not sure what to do to support that single statement, or ask her out to something. I live by the idea that, yes, if you overtly don't handle things well, it won't work, but if you can handle that, then the more subtle stuff that supports that idea is very important, and I'd be very surprised if that did not apply to the most complex and special parts of us human beings interacting with each other.

As for "special education," I was more referring to the fact that generally things labeling themselves as that just have no idea how to actually help people who function differently, and just end up pushing them into depression and screwing their lives over. I think that kind of thing also makes kids in that appear from the outside to be "crazy" or "too far gone," and maybe that's because they're crapped on by the worst aspects of the school system My current school is very lenient and supportive in the areas that I need some breathing room and help most in, which I would not hesitate to call a miracle.

I'm tired, gonna go to bed. Goodnight!

[Sam W]

I think it's likely that you're already doing some of the things that will signal to her that you care about her and your relationship. When we're friends with people, that kind of behavior tends to arise naturally. That's part of why you have to pair explicit declarations of interest with those subtler behaviors, because the ways we show care and affection for people can be similar for friends and for partners.

In terms of worrying that she'll thing the only thing you care about is your relationship, you can fall back on some of the advice from that "puppy love" article. If you're still spending time with other friends/family, on hobbies, on school, etc, and taking care not to spend all your time and attention on her, then odds are good she'll be able to see that you care about lots of different things.

[Estobawk]

I think you guys have given me some good advice. Thanks for talking to me and helping people like me with your awesome website!