I say this coming from a dude who also used to be overweight, insecure and way too concerned with chicks...but dude, pull yourself the fuck out of this. First off you need to separate yourself both from this chick and probably most girls in your life for a while, because when you're lonely you see shit that isn't there and hope for things that both won't be and shouldn't be.
Then, m'friend, work on whatever it is you need to do to fix yourself. Whatever your insecurities are, fix the problem. People telling you to stop feeling insecure isn't going to work, I know that, so just do what it takes and fix what's *causing* them. When you are seriously ok with who you are, people know that. Even people who aren't that conscious of themselves or other peoples feelings have an innate ability to read other people through body language. You can't fake confidence, people know. And when you can look yourself in the mirror and know that there isn't anything more you could be doing to be a better you, cheesy as that sounds, that's when you've reached a point where it's damn near impossible to still feel insecure. Remove guilt from your life.
Cause I'm gonna level with you, every post I've seen you make about chicks reminds me of a 16 year old me. And that guy was one awkward mother fucker around the ladies, fo' realz. You're still young and have time to fix that shit in time to be young enough to reap and enjoy the rewards. My first suggestion is start working out religiously. You force yourself through the first three weeks and after that you get not only the joy of the weight loss but the exertion and endorphins will keep the tension away and leave you with a feeling of just being more ok with things. And if you're even remotely like I was, and you don't have to say whether you are or aren't, a lot, if not most, of your guilt and insecurity comes just from being that overweight and feeling like you've just let it happen and continue to do nothing about it. If you put in even half the effort I did you'll be fit, thin and possibly buff in a year and a half, two years. You work *as* hard as I did, it could happen in 6 to 9 months. And the work *is* worth it because I don't feel the need to use kid gloves with a guy in his mid twenties, you're right, being a fatty fat fat makes finding women extremely difficult. Most girls don't mind a guy who is 10, 20, hell, maybe even 30 or 40 pounds overweight, depending on your height and frame and how well you can personally pull that off, but once you've hit 50 pounds over what you're supposed to weigh, you better be damned rich, damned successful or damned lucky if you expect to find a halfway decent girl who goes ga-ga over you. That is, unless, you're one of those guys who is genuinely and truly confident in spite of their looks *and* has the character and charisma to pull that off (Hint: You aren't, or you wouldn't be posting stuff like this)
Just don't half ass it, do it right. Keep the calories in the 1200-1800 per day region for a while, and make sure you work out at least 60-90 minutes a day. Use Cardio only as a warm-up and cool down, at first, and focus on building muscle which burns more calories even at rest and then add in more Cardio over time when you're more concerned about stamina and fitness than appearance. And, lastly, listen to Night Owl. Women don't belong on a pedestal nor do they want to be there.