At a bar a couple towns over, one of those big ones where the line between club and bar is pretty thin. Opened a couple sets some with positive response's but none were really keeping my interest. I'm pretty shy so it takes a couple of sets for me to build my confidence up.

Eventually I saw her, really cute girl obviously third wheeling with her friend and her friends boyfriend.

Money.

Her friend was sitting at the bar with her S/O, Lisa was standing behind them. I was standing with my friends right next to the set. She caught me looking at her so I had to move immediately or look like a creeper and forever lose my chance.

It happened so fast that I hadn't really thought of anything to say to her so I opened with a lame compliment "I like your sweater" and accompanied it with a big ear to ear smile.

She replied with a rather confused "you like my sweater?" (sweater was rather ordinary). I knew I had to own it, so I went on about the thread pattern and B.S.'ed about it until she cracked a smile.

She is much older (6 years), but we really hit it off. I had the social proof of my friends nearby. Her friend eventually started talking to me too. I played it well and gained her trust and let her vouch for me. I knew I was in when Lisa's friend told her I was cute.

We spent the rest of the night talking and dancing some I had a blast. Got her number and nailed a kiss close. Definitely want to take her out one on one, possible GF material.

What I learned:

  • Warm-up! Flirting is like a muscle if you don't "stretch" it you're gonna pull something.

  • Sometimes the best pick-up line is a genuine smile

  • Don't lie about your age to an older woman. This is a mistake I've made in the past, in my experience doesn't work.

This is where I need your help Reddit

This happened on Friday, the next morning I discovered that one of my very close friends passed. The whole weekend has kind of been really depressing after this highlight. I haven't texted her yet and I feel conflicted as to when I should. Obviously sometime this week I'm going to be burying my best friend. Most likely I'm going to wait until after the funeral and services to reach out to her but I fear waiting too long.

Say she wants an explanation? I'm uncertain about opening up to her and scaring her off. Or if I don't mention it and she finds out later I seem sketchy for not telling her.

Thoughts and advice appreciated.

edit: formatting