Relationship Advice

Based on an experience similar to yours, I can tell you need to be honest with your intentions and feelings (with yourself first and foremost, and with your crush afterwards).
A friendship in which one side wants more than the other is usually not healthy and not viable in the long run. That builds resentment and regret.
Keep in mind that a lot of women are put in uncomfortable positions when faced with a situation like this. It can make them feel used and the longer you wait to be honest with your intentions, the harder the fall will be for both of you.

I think approaching this in a level-headed, communicative way is your best option. Steer clear of openly professing your love for them, just ask them if they'd be interested in going on a date. In your shoes, I'd also make it clear that I value their friendship, and if this isn't something they'd be interested in the last thing you want to lose is a good friend. Feelings happen, handling them in mature way when they aren't reciprocated is the key to not burning that bridge. No matter how bad a "no" might hypothetically feel, not knowing and living with that regret will always be worse. On your other notes about how you see yourself, I've been there too. Clothes that fit and a nice haircut can do wonders (not assuming you don't do these things, just putting it here in case). All that aside, you clearly have a lot to offer as someone they enjoy talking to so frequently. Remember that when you ask, confidence can go a long way.

i'm sorry that you think of yourself as ugly. you seem to think of yourself as significantly lesser than her as a person. you describe her as all the positive things and then beat yourself up and call yourself ugly. i think you should rebuild the relationship that you have with yourself before trying to focus on a relationship with another person. enjoy the friendship with her for now while you work on yourself, and in time, your friendship might progress into a relationship. whether or not you do end up together as a couple, i'm sure she would love to see you become more confident and secure with yourself.

So I'm a millenial, so we may have generational texting ethics that don't align. But:

If she wakes up before me she always says good morning and ask me how's things.

If she is frequently texting you first thing in the morning, that's a strong indicator of interest. Are there any hints of flirtation in the texts? Or do they stay on the topic of work?

I'm seeing a lot of people saying take the chance.

At the same time I can't help but think how disappointing it must be as a woman to not be able to have a platonic friendship with a guy without them thinking it's something more or wanting it to be. Maybe she thinks you're just a decent friend. If you take that shot there's a good chance she'll keep her distance in the future.

On the flip side I can't help but think of all the stories of girls flirting with guys who are completely oblivious.

Not enough info to make a good determination, other than life is short and you're young, you can afford to take a risk or two. Personally, I wouldn't but that's cause I'm a coward.

You talk for hours at night, she goes back to talking to you first thing in the morning, she compliments your looks, puts hearts next to your name... I could just be kind of naive, I'm no expert on love at all, but to me those are all good signs she could be interested.

I'd say ask her out? See some movies together or something, meet each other outside of work, see how that goes. Just hanging out together for starters, I think that'll tell you both all you need to know about how the other feels. No need to rush into romance and dramatic declarations of love, take your time and treasure the friendship first.

From the sound of it, if she does share your feelings the transition will happen all on its own. Don't overthink things too much, at the end of the day if you two enjoy each other's company, just spend more time together.

Shoot your shot or it's just going to eat at you forever. Don't go overboard and crazy with it though.

I wrote a long comment that got lost. Uh...

TLDR If the feeling is mutual it's about not fumbling the ball more than racing to the finish line. Work on yourself if you aren't proud of who you are. Strengthen friendships, especially mutual ones. Treasure the feeling and be kind to both of you.

I think the answer is easy. When you get a chance, while you two are alone and in a good mood laughing and just having a great time, ask her if she wants to grab dinner some time. Just that simple statement, in a curious and inviting way, and then if she says no just say “okay, no worries! The offers gonna stay available in case you want to sometime later”. If she says yes, ask what day works best and set a time, tell her you can pick the place and surprise her if she wants. Go from there. Godspeed.

Most women respect honesty. If you tell her how you feel now, the two of you can work out whether she feels the same and wants to move forward, or if you two should just keep it light and casual and if you can handle that. If you carry this torch, though, and don't tell her, it's possible you'll get resentful and then she'll be resentful when you tell her, thinking your friendship had ulterior motives.

Get it into the open, and go from there. Maybe she likes you back, maybe she doesn't feel that way but you two can still be friends, maybe it's a crush that'll dissipate quickly.

So here's what can happen:

1. You profess your feelings, she professes hers back in kind, hooray!
2. You profess your feelings, she doesn't feel that way, you stay friends and you have to FULLY give up on your romantic feelings toward her (otherwise it's something that will always be hanging over your friendship [I think this is the hardest option for you]).
3. You profess your feelings, she doesn't feel that way, it's too hard for her to be friends knowing you'll always want something more and your friendship is gone, you both move on.

I'm definitely missing some more nuance, but these are kind of the broad categories I could come up with. The questions you should ask yourself are: is it worth the risk to act right now? Do I have enough information to make a decision on this? If not, how do I get more information in order to make the best choice?

Also if it's only been in the past couple months you've been growing closer, give it more time. Like several more months. If it continues to develop, you might get all the information you need!

It’s kinda hard to say, from info given, what she might be thinking. Has she indicated, in any tangible way, that she’s interested in more than friendship? In my experience, a lot of men think a woman is interested because she’s simply being nice to them, and enjoys a friendship with them.

I know I’ve personally experienced it a bunch of time. I become friends with a guy, we text/chat/occasionally hang out, and then a month later he’s professing his undying love for me, and all I’m left wondering wtf happened (not saying this is you) to make him think that was my intent. I was just being friendly ffs.

Also, having a work/professional relationship makes it even more complicated. Are you peers? Are you higher in the food chain than her?

I guess what I’m asking, in not the most elegant way, does she flirt with you, or show you she’s interested in more than friendship?

Honestly, as someone in a relationship with a person who I thought was solidly, stratospherically "out of my league" at first, I can tell you the concept of "leagues" is wildly inaccurate (even though a part of me is still convinced that she is way out of my league).

Two things matter here:

1. Your ability to be yourself (or an improved but still faithful version of yourself). Don't pretend to be something you aren't, that isn't going to end well regardless of the possibility of a romantic relationship.
2. Your ability to accept and get over rejection without affecting your current relationship. You have to be able to be confident enough that if you ask her out and she says no, you can say "hey, no worries, that's cool" and mean it so she doesn't have to worry about you being weird about it subsequently. You also have to be able to accept that if she doesn't reciprocate your feelings, she might be slightly distant and less trusting of you for a little while subsequent to whenever you do ask her out. Do not overreact or overcompensate for this in any way whatsoever. Treat her exactly the way you have been all along, as friends. If you think you can't, step away for however long it takes you to manage your feelings, and be kind the whole way through.

Now that we're clear on that, see how your time together next week goes. If she seems like she genuinely enjoys having you around, ask to hang out again in a more informal situation. Invite her out to something you think she might be interested in. See how that goes. If it consistently goes well a couple of times (for both of you), gently bring up how you feel and tell her you'd like to ask her out on an actual date, and be guided by her response. Judging by what you've told us up there, your chances are already looking pretty good, because she seems to enjoy your company a lot.

Tl;dr -- be yourself, be brave, and most of all, be (genuinely) kind. You'll be all right one way or the other. Good luck!

I recognize this probably isn't super helpful, but I think you should just go with the flow. Keep going as you have been and see what develops from there. You'll find out soon enough whether she's interested in you in that way or not, and if she's not, you'll have only strengthened the friendship that you value so much. Let it simmer, my dude, no need to rush the sauce.

Just take her out on a date, not a romantic date but a fun date.