Valentine's Day + another question

Alright, this will be a 2 part question.

1. I moved in with my friend for about a month in the summer, we got our own place, the only problem was his girlfriend was also living with us. At the time, I had no problems with her girlfriend. My friend and I both worked security for the same company, although at the time I was laid off, and he'd go to work every night, leaving her and I at home alone. The first night we moved in, she was in the shower and she yelled my name so I went to the door, and stood outside of it and said "what", and she tells me to come in, note that the shower thing is a glass sliding door and it's see through. Now, all she wanted to ask is if I could find her body wash in her room because she forgot to get it... alright, why couldn't you ask me that with me being outside the bathroom.
Anyway, that only started it, during the whole month she'd have these deep conversations with me and say how she doesn't want to be with my friend Steve anymore and she'd flirt with me, literally every night. Now, although I did grow feelings for her, I didn't let that get to me and ruin the friendship my friend and I had. One day I just started ignoring her and not showing her the attention that I was previously giving her, and that really pushed her over the edge, so when our one mutual friend came over, she takes him in the other room and starts saying things like "I'm gonna tell Steve that Joe likes me and that he flirts with me every night" And shit like that. So our mutual friend, Travis, came and told me that which I laughed about.
That wouldn't be so bad, except she got drunk that night so she started texting Steve at work and causing problems, and he started getting mad at me, so I told him a secret that she's been keeping from him. After I told him the secret, he thanked me and we were cool again. As the weeks went on, I simply told him that I couldn't live there anymore because his girlfriend was giving me an attitude and being a bitch to me, which was only partial of the truth lol. So he told me things like "Yeah it's cool man, I understand, it's probably weird living here with a couple" and so on and so forth, I gave him the month's rent + electric + internet, and moved out that day.
Now, upon leaving, I never told him the truth because he most likely wouldn't believe me and she'd just deny everything, and I honestly don't even want to get on his bad side because he's a bodybuilder so he could fuck me up real quick. The thing is though, I didn't tell him the truth because I didn't want to ruin our friendship, and he said even though I was moving out, we'd still be cool. But as the weeks went on of him not texting me, I texted him finally and wanted to see if he wanted to chill for a bit, so I went over his place and hung out for a few hours but it was awkward for some reason. I then waited again to see if he would provoke us hanging out, but again, he didn't ask me to hang out for a month or so, so I did, and I went over his place and played xbox and slept over, but again, it was awkward and it didn't feel how it used to. It's been basically 2 months since we last hung out and I decided I am not going to be the one who initializes us hanging out, and if he doesn't initialize it, then clearly he isn't my friend, you think he'd at least text me or something. But that's the problem, his phone got shut off so he has to use his girlfriend's so it's weird texting him because she sees everything. If he had his own phone, I'd probably just tell him the truth about her and shit.
So what do you guys think I should do, should I just wait and see if he asks me to hang out or something, or should I just cut my losses and move on? I consider him my best friend, well I did, and it would suck to lose him, but if he's a fake friend, then fuck it. But then again, maybe she filled his head with shit and mislead him, so idk. I was thinking about messaging his dad on facebook and have him have Steve get in touch with me, but like I said, I probably want to wait and see if Steve gets a hold of me at all. What do you guys think? I'd like to hear your input.

Now, as for the second question.

To start off this question, I'll begin by saying that I used to be 360 pounds, but after I started working out and lifting, I cut down to 268 currently, but I'm not even that fat, due to me lifting, I have a good amount of muscle too. The reason I lost the weight was to join the Army, about 20 pounds to go. Now, because of me being 360pounds, or overweight, rather, for most of my life, I lack the social skills required to socialize with everybody because I used to be so embarrassed to talk to anyone that wasn't on xbox because they knew what I looked like and I had an image in my head that they're all judgmental. It's not that I lack the confidence to talk to anyone, I have a lot of friends and a lot of friends that are girls, but I lack the resources to introduce new friends into my life. The only way I make new ones, is if they want to be my friend and they make the effort, which is always the case because generally I'm a chill dude and pretty nice to everyone and I make people laugh, I just am not able to hold a conversation with people, I honestly just don't know what to say, I don't want to say something stupid and bore them, and so on and so forth. Especially when it comes to girls that I like, I don't want to say the wrong thing.

Now, I'll just lay it all out, because I don't know how to write all this so it looks neat. Alright, so this girl and I went to school together, and after I graduated, she started texting me, and we text maybe 2 days a week, if that. She is usually the one who starts the conversations. Whenever she says something, I really don't know what to respond with, so I just write "yeah lol" and "me too haha" and so on, I give her very vague messages, but I'd like to give her more than that and have her think I'm interesting. She asks me to come over and play nazi zombies with my xbox every now and then, and I did that twice, but shortly after, I sold my xbox to get my weight bench to get in shape for the Army. Now, I don't know what I can do with her, whenever her or I want to hang out. I'm trying to get money around for another xbox so I have a gateway to opening up a relationship with her, but it's taking a bit to get one, and I'm going in the Army soon.
Now, I saw her posting on facebook 2 days ago that she's "tired of being single" and "I wish I had a valentine for valentine's day" which got me thinking, maybe that's my ticket. The thing is, I don't know how to ask her, or what to do with her on valentine's day. Say I took her to dinner and a movie, it would be boring as hell because I literally wouldn't know what to talk about because I don't know her that well so I don't know what she likes to talk about. And the next problem that comes to bay is that, what if she doesn't like me like that? What if she truly just sees me as a friend? When I used to be ginormous, I used to have girls that just wanted to be friends, because of my size of course, but now, I'm I guess scared to try and get a relationship going lol.

So basically, if you read this wall of text, thank you lol. If you understood the questions and points I was trying to make, thank you again, and if you guys could please truly help me out, that would be swell.

 

Phew, long read but it's okay. For the first question I would wait a while and see if he hits you up. If not, just ask him that you and him should go out to lunch/dinner sometime, then let him know that you guys haven't hanged for a while and you should start chilling again. (You could also tell him the truth about his girlfriend situation, but that will probably make things worse.)

As for the second situation, you should go for it bro. Just hit her up and say hey what are doing on Valentines Day? Nothing? Oh we should go check out this movie or something among those lines...

Going to the movies they is not much to say only when your getting your tickets. Then, you can take her home or just do something else. To keep the convo going, you just gotta make the most out of her sentences. Analyze what she says and basically twist those words around into questions to keep the flow going. Could also just ask, what did you think of the movie? I didn't expect XXX to happen, that was crazy! Get jiggy with it.

Best of luck friend.