I just had my first successful approach in my life but I’m not feeling too confident about it. Last night me [23M] and my 2 male friends (same age and sex) went to a middle school playground to pass some time before one of them leaves for vacation in the morning. It was dark outside with minimal street light and we were on the swings. One of my friends Sam spots a silhouette of a skater on the other side of a tall fence where the basketball courts are. He seemed pretty sure that the skater was a girl, but I was certain it was a dude. He was very adamant about it and I stubbornly argued my position, so it escalated into a big debate about the skater’s gender. We decided to make a wager for a grand total of $1 to determine the gender. My other friend Pete bet Sam the $1 to walk all the way over there just to confirm and put an end to this utterly pointless pondering. He chickened out because he didn’t want to make it feel awkward and creepy. As they kept arguing, I got up the nerve to walk all the way towards the skater. Sam noticed me walking and soon tagged behind me while Pete hesitated. To my surprise, it turned out to be a girl about my age, and a very cute one at that! I say hi to her and spark a little small talk as my two friends eventually join me on a bench on the other side of a small fence close to her. I ask her a few questions about skateboarding and her life as Sam butts in with a few conversation pieces of his own. Eventually the conversation settles down as she hints about wanting to return to perfecting her ollie by putting her earbud back in her ear. Her body language was clear so we eventually decide to leave. Pete did not join in the conversation at all and was the first to start walking. Sam then started leaving but stopped in his tracks to listen as I stayed behind. I worked up the courage to interrupt her one last time to ask for her phone number. As much of a nervous wreck I was, she obliged! She first asked if I had an Instagram, but I had to tell her I didn’t since I don’t really do social media. This didn’t turn out to be a problem since I eventually got her number and full name. Before we say goodbye, Sam butts in again to ask her for opinion on the shirt I was wearing, settling another dumb debate we were having earlier in the day. Turns out she liked it so another score for me! As I was walking home with Sam I was in high spirits about successfully getting a pretty girl’s number and winning one whole lucky dollar.
However, when we got back to my house, Sam found her IG and a bunch of other info about her on various social media sites. Turns out she's too cool for me. She travels, knows kungfu, has two pets, is learning to skate, and left her family to come to this country to pursue her dreams. She also has a GoFundMe, a LinkedIn, and a pretty presentable website. So my question is how do I impress her? Me, a person with depressive tendencies, anxiety, and no real accomplishments to speak of. How do I overcome this lack of confidence? What can I do to compensate for the gap in social status and self-worth?
P.S. She lives in my neighborhood, which is convenient but goes to school in a city 4 hours away. So I really only have a month’s worth of time at most to do anything about it.
*TLDR: *Successfully got girl’s phone number, but later realized she’s out of my league in lots of ways. Need to know what to say/do to get over this slump I’m in.
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