That being said, I've been exercising (and I look amaaaazing), experimenting with new styles, taking lessons (saxophone, voice, ballroom dancing), starting a martial arts class, and have taken up archery. SELF IMPROVEMENT GO.
Some of those lessons, especially dancing and martial arts, must be social. Do not view them as means to an end (self-improvement); view them as what they are: part of your life. Those social experiences with classmates and teachers are opportunities for you to learn about yourself and others.
My goal is just to get more social and be more confident around lady-friends. I'm not super-awkward, but in the back of my mind I'm always second-guessing myself and wondering if I'm putting them off even if they seem to be enjoying my presence.
Yeah, that sucks. I think we've all been there. It's easier said than done, but stop thinking about it! If they aren't 'enjoying your presence,' either they will let you know, and leave, or they're patient/kind enough to spend time with you anyway, so it's not your job to decide how they feel about you.
Girl 1:
I picked her for my first date because she's cute, a little awkward (so -I- am not the awkward one), and very easy to approach.
This is incredibly rude. You 'picked her' for a training run, you made sure
she was more awkward than you, and that you felt comfortable approaching her. That was not thoughtful or kind.
You worry about people disliking you, you still partly see yourself as a 'lame boring fat guy' - what that means you picked a girl that you felt confident around, a girl who would go out with a lame boring fat guy, i.e.: a girl below your standards as a gym-going, self-improving, confidence-gaining guy. I don't want to sound mean, but that was a date for your ego.
Here are the problems:
- She will only talk via text (no Facebook or anything), so any text I send has to have -purpose- and can't be chit-chatty like Facebook
- We have no mutual areas where we're ever likely to hang out, just randomly see each other, or anything. It will always be a "Let's meet here, and do this thing."
- She still lives with her ex (until March) and doesn't like being in the house, so getting out is easy to convince her to do. BUT, that means we can never "just chill" at her place, and my place isn't very "just chill"y either, as it is a shared space and I don't think we're close enough for me to invite her over yet.
- It's flippin'-ass winter, so all activities need to be inside. We can't just get lunch and go for a walk outside.
- We are BOTH awkward and bad at talking, and while I'm working on it, I'd like to work on it a bit at a time. I'd like to avoid a straight-up dinner where it's nothing but the expectation of talking. (I always found dinner dates crazy boring anyway. I like more spontaneous fun.)
- I would like to re-introduce her to our really big group of friends, but that group includes her ex, so she doesn't want to be around him or his new gf. What are good ways to get her to hang out despite this, if possible?
Okay, so you picked an awkward person: now you discover she has awkward habits like only texting. Surprise!
Seriously, though, I don't know how cold it is wherever you are but you can totally go for walks in the winter. Make snowmen, have a snowball fight, just admire the way snow clings to the branches of the leafless trees, suspended in cold serenity. So don't rule out the outdoors. Also, if she lives with her ex (?!?!) then she already sees him, so being in a group of friends that includes the ex is probably not bad, maybe even good; she can talk to other people, while not having to focus on her ex's presence, but being comfortable with him around.
You're close enough to have her over. My second date with my current girlfriend was me cooking dinner at my place. You want to stop overthinking? You want to be confident? Do the things you've overthought! "What's the correct number of dates before you invite a girl to your place for a date?" I slap people who ask me that. The answer is: Do you like her enough to spend time in your apartment with her? Watch a goddamn movie, cook her dinner. Yes, you can cook; shut up, it's called Google, keywords "easy date dinner recipes"
So I'm looking for things that I can invite her to where it won't be a situation where we have to force conversation too much, and be able to enjoy -doing- something, that is indoor.
Go bowling. Go swimming. Go to a gun range. Go go-karting. Go dancing - find a ballroom dancing club and show off your lessons. Share your life with people, and conversation doesn't have to be forced. You are not one person: you're two people dating. You don't get to decide "I am the self-improving individual who dates" - no, that's just a narcissistic belief that somehow you're the main character in your life.
Girl 2:
I started chatting with a girl that's been in our group for a while on Facebook, and she's pretty awesome. Loves puns (one of my favorite forms of humor), laughs at poop jokes (huge plus), is funny, likes Disney (big for me), and plays video games (cool, but I've played a lot less recently).
I would say we chat easily enough, and she certainly doesn't come off as short and does seem to enjoy our chats, but I tend to overthink and wonder if I'm being annoying, pushy, or anything like that. She started asking what videogames I liked and then I realized I didn't have much to say on it, so I felt like I was unable to keep up interesting conversation (but it may not have been that way at all).
It probably wasn't. Talk about classic games, or games you played in the past, maybe you have some shared good memories there. Again, if she's bored and not telling you, that's on her, not you.
I was going to tag along with her to Campus Movie Fest (she contributed to a movie), but due to snow it got rescheduled to next Friday, which was kind of killer on timing and pacing of initial friendship to me. So instead we've just chatted a bit, but I'm going to lay off a little just in case I have talked too much.
Argh timing and pacing of initial friendship? There's no timing and pacing. There's no chart! There's no graph! STOP IT STOP IT. Your friendship isn't timed and paced, it isn't an apprenticeship, you don't put in your hours and get the next level.
Also just talk to her. "I'm not going to talk to the girl I like in case I talk too much because I like her." I want to play any strategy game with you. "I'm not going to bet on this royal flush because then other people will know that I have a good hand they won't bet and I won't get any money."
Next Thursday my friends and I are planning a game night and inviting some of our usual group, so I asked if she would be interested in that (and offered that she could bring along her roommate or anyone else). She said, "Oh sure! I'd have to get more details before I can say for sure but that is definitely something I'd be interested in!" which at face value is mostly a yes, but I know girls, and I know polite girls, so this could be a polite maybe.
It could be a polite maybe. So you call her up, give her the 'more details,' and an RSVP by. "We need to know how many people are coming so we can..." xyz excuse. Get the correct number of chairs. Whatever.
I told you I overthink things. ANYWAY, I'm trying to tell myself it's cool, just be a fun person, but in the back of my mind I'm still a really lame boring fat guy from 5 years ago. I've got ugly duckling syndrome. XD
You might, but more importantly you have a very self-centered view of things.
I'm exercising,
I look amazing,
I am improving
myself.
My goal is to be more confident around girls,
my goal is to be social.
I picked Girl 1,
I'm working on talking,
I want to avoid dinner-dates that
I find super-boring.
Great, exercise is good; it's good you're feeling good about how you look. You're improving yourself? Not yet. You're doing things that will hopefully lead there though. But your goal is to be confident with girls, i.e.: you want to be perceived a certain way based on the validation of others' feelings about you -
this is literally the opposite of confidence. A confident person is not confident 'around girls', they are confident because they are comfortable with who they are; they know that people may dislike them or think they're ugly, or lame, or stupid, but this doesn't faze them, because they know that they have no say in others' feelings, and the kind of people they want to be around are the kind that want to be around them.
You picked Girl 1? She didn't pick you? She didn't say yes? She wanted to go on a date with you, too, don't forget that, don't forget that she also liked you enough to go on a date with you, and conversation was awkward -oh, you make sure to mention that
you are working on it, but what does that mean? She's not? She's doomed to her awkward conversation skills? You don't want to do boring dinners; what about her? Would she enjoy a dinner date? Would being on a date that makes you uncomfortable cause you to practice these skills of socialisation, conversation and confidence? Yeah, it would.
A dinner date sounds like it would be great for the both of you to do. Then go for a walk and admire the wintertime.
Anyway. Any advice on Girl 1 regarding things to do, and any advice on Girl 2 regarding not being lame while chatting with her?
Think I've covered Girl 1.
Girl 2: you are who you are. Do you still like games? Play a few - in fact, ask her for recommendations of some to play. Bam. Things in common to chat about.
But as a general rule: ask questions. You'd be surprised at how many people love to talk about their jobs, their family, their hometown, their uncanny ability to remember every single phone number they've ever dialled...
tl;dr I have not dated in a long time and I still feel very lame
You're not lame. You're self-conscious and your intense overanalysis of your own behaviour is letting you neglect the reality of other people. Share things about yourself with them, and invest in their lives, and you will have many friends. And people are going to tease you sometimes, and love you anyway, and people are going to have nothing against you and hate you anyway.
This is called
people.
And again, -pure- conversation is awkward for us nerd-types. That comes later when you have more to work with.
"Pure" conversation, whatever you mean by that, but I'm assuming a situation in which there is facing each other and talking? Anyway, it isn't awkward for us nerd-types. Don't use a label to excuse yourself. "I'm an introvert, so I can't meet new people," "I'm a nerd, so conversation is awkward." Maybe introverts have a harder time meeting new people, but should they not socialise? Of course they should!
How they socialise should be different, because, people are different, duh, but the point is that you can't just runaway.
Aren't you trying to improve yourself? Throw yourself out of the nest, then, fly or fall, whine, and jump again and again until you have great conversations. Ask questions ask questions ask questions.
And not yes/no questions
Ask what they do, what a day is like, how close they are with colleagues. Ask about family: cousins! Great-uncles who were hanged for horse rustling (I have one of those!)
Your comment "That comes later when you have more to work with," is baffling: the more to work with
comes from conversation. I know, I know, you want
small doses of conversation during an activity so you can later on have 'pure' conversation.
Pff
Fly