How to Beat the Single Girl Blues
I Date Single Men with Cats & That’s Why I’m Still Single
Why Men are Intimidated by Successful & Independent Women
4 Signs You Fell in Love With Your Hook Up
To Smile or Scream? Millennial Views on Uncircumcised Men
I’ve Been Ghosted by Every Man I’ve Been in a Relationship With
This Is Why Men Always Ghosted
Sex on the First Date: Do Men Think You?re a Slut?
Why is His Dating Profile Still Up?!
You’re Thirsty! 6 Desperate Things Men Do on First Dates
Don’t Know What You Want? You’ll Date Dogs
Snooping in Relationships: Is It Ever OK to Dig Up Dirt?
The Trouble With Men Who Lack Confidence
Love at First Sight: She Had Me at Alabama Slammers
Why Some Single Women Get A Sweet Tooth for Sugar Daddies
My Fiance Cheated and Got Another Woman Pregnant
Confession of a Female Player: How to Play a Man Like A Man

“Unlike a lot of the other people I know, he’s not particularly good-looking, is overweight”

Long as he’s out-going and charismatic, that stuff won’t really matter…as you found out. :)

“I notice something different about the way he interacts versus how I interact. Unfortunately, this interaction I can’t remember as well, but in general, it was/is hard for me to get anyone’s attention/enthusiasm. Whereas, he got into several sustained, fun interactions.”

Good, pay attention and observe him in action. I’ve learned a lot from watching and running sets with buddies who are good with chicks and comparing what they do to what I do.

Got some suggestions for where you’re going wrong coming up.

“I also notice that I don’t have that many interesting things to say, beyond stupid shit like ‘that’s an interesting scarf/jacket….it’s like a [insert random observation]””

This is a good thing to do in general…I think the problem you’re running into is that you’re waiting for the girl to contribute something to the interaction after you say that kind of thing, but you haven’t passed the Hook Point yet (where they go from “when will this guy leave?” to “I hope this guy never leaves!”) so the girls don’t want to contribute yet. Your buddy sounds like he’s passing the Hook Point with the group, thus he’s getting sustained interactoins and attention/enthusiasm.

Essentially you’re both on skateboards kicking the ground to get moving but you stop kicking and stand on your board too soon so you lose your momentum while he gives a few more kicks and makes it to a downward hill and sails along.

“I pick up the vibe that she’s trying to shoo me away”