Developing feelings for a longtime friend, I could use advice!

[Mets]

Hey everyone,

I know this is really long, but if you are willing to read through it I could really use your help. Oh, and don't worry all the names are fake, I just want you guys to be able to follow along and not get lost.

I am a 23 year old guy, average looks, on the short side. I consider myself to be a pretty normal guy. I've dated girls before, my longest relationship lasting for two years. I've also been rejected before, and I'm certainly no stranger to it. That being said, I've always been on the quiet side with people I don't see very often, and I've never considered myself to be a great flirt.

I've been trying to deal with something for a couple weeks now and it's been eating me alive. I really want to know what other people think about this.

I have a female friend who I've been friends with for a long time. Lets call her "Sally" for the purpose of this conversation. We've probably hung out together with our friends a hundred times, but never just us. The group we have consists of me, and my two best friends, who are both guys, lets call them "Mike", and "John". Mike and Sally have a really close friendship, and I'm moving in with Mike in a couple of months. You could see how this is already complicated...

Lately I decided to start talking to Sally more than I have in the past. Once me and Mike move in together, I'm going to be seeing more of Sally and so I wanted to get to know her better. I had no intention of dating her or anything, I just wanted to become better friends - up until now.

A couple weeks ago most of my friends were out of town so I asked Sally if she wanted to meet up for a drink with me and John downtown. She brought an extra friend and we all hung out just as friends, but it felt awkward. Usually Mike is the glue holding the group together and without Mike there we were all a little quiet.

I've known Sally since high school, I've hung out with her a hundred times and never had feelings for her. But suddenly after I got home that night, it hit me like a ton of bricks. Things had never felt awkward between us before, but suddenly on the one night when Mike's not around to hang with us we ended up fumbling for things to talk about? I only get shy around people who I like or don't know well. And I've known Sally a long time... and I suddenly started looking at her in a different light. I started thinking about how much I like her as a person, she's one of the most genuinely warm hearted people I've ever known. And I like the cute way she smiles and her self depreciating humor, I like that I can tease her about anything, and she'll always play along. Most importantly... I feel something more than just friends when I'm around her. She's such a cutie, and I feel like I've been wearing blinders for the past 8 years.

The day after we hung out, she texted me saying "Heyy, I'm sorry we were so lame last night"... to which I responded "You weren't lame it all, I was the lame one", and I tried to just start over from there. Ever since I've been trying to flirt with her, and see where it goes. Sometimes, she seems into it, other times she's not. She's a naturally flirty person so it's hard for me to tell.

This past week I went on vacation to visit my family for thanksgiving, and I thought it would be a good opportunity to text back and forth a lot. In the beginning of the week we were flirting a little - when I told her I was gone for a week she said "You should have thought about this before so I could have just hopped in your suitcase!", and we went back and forth for a couple days joking about how to smuggle her down the coast... I sent her a song I wrote on the piano which she said was REALLY amazing and she told me she sings.. so I told her I thought it was cute that she sings, but she kind of sidestepped that one.

I don't know where I stand though. Mid week, I thought maybe I should back off and give her some space, especially after the "cute" comment. But she messaged me on facebook just to talk, she texted me on thanksgiving, and then texted me again on Saturday to ask "Heyy, are you still on vacation?" I thought to myself this is three times in a row, this text has got to a good sign and I told her I was still away but I was coming home tomorrow, to which she responded "yayy" and then I threw a little quip out there "Did you have fun without me around?", but she didn't text back, which was confusing.

I got home yesterday and I knew I needed to talk to Mike about this. He practically considers her to be like a sister. I told Mike I just wanted him to be honest with me about how he felt about the whole thing, and he was. He told me he doesn't want to tell me what to do or anything, but he thinks it's a bad idea. He doesn't think she would do anything that could potentially backfire and break up our group of friends. He said Sally is a flirty person, and she'll flirt with you because she flirts with all her friends (Which is true). He also felt like this came completely out of left field and asked me if I just like her because I don't have that many girls in my life right now, but that's not it at all. Ultimately I thanked him for his honesty, and he thinks I should do what feels right to me but it seems clear to me that he's against this.

When I talked to John about this two weeks ago, he told me at least try - and he thought we'd actually make a good match. But when he heard what Mike had to say he did a total 180, and completely agrees with Mike now.

I'm really torn. I want to see this through, but I don't want this to damage my friendship with Mike. Especially since we're going to be roommates. And no matter what happens, I have to see Sally a lot. I think there might be a spark here, otherwise why would she keep texting me and flirting with me? But I don't know if I'm just trying to see what I want to see and making too much out of it...

I want to ask her out and if she makes up a bunch of excuses then I'll just have my answer, I'm just really torn up about what to do.

Help me decide!!! I've haven't felt so conflicted or even thought this much about a girl in a long time... Help me!! I need your advice haha

[BackUpOrGetStng]

I think you should just tell her and get it out of the way. Tell her how you feel, that you just needed to get it out, and you're not going to hold it against her if she says no. If she starts fumbling and coming up with excuses, don't let her finish, just say, "I get it, it's cool, I won't bother you anymore."