Recently I found the confidence to straight up ask girls out.

I’m 33M, and have been what I would consider shy for most of my life, very tall, ok looking, sometimes confident, but still sometime shy. Also, most of my life I’ve been obese, but I lost 70 lbs over the last year, so that probably added to my confidence. I’m currently about 25-30 lbs overweight, and still working.

Like I said, recently, after I started going out a little more since Covid, I’ve found that when I’m interacting with an attractive girl or woman, and I feel some kind of chemistry, instead of leaving the situation unsatisfied, I decided fuck it, I’m gonna tell her how I feel and see if she wants to hang out sometime.

I’ll give an example of two below but generally, they’ve been very positive experiences. I haven’t got a date out of them yet, but most of them have been solid positive experiences. I walk away feeling super satisfied, I’m happy, she’s happy, everything feels good.

But tonight I asked out a waitress at the end of my meal, and it didn’t feel as good, it felt a little awkward. Here’s a quick breakdown of tonight:

I saw this beautiful waitress at a really nice restaurant who was really tall, like me. We caught eyes early on the meal, and halfway through I asked her over to the table to light my candle (I was with my dad). Casually, I mentioned her jade bracelet and said I liked it, she lit up at this. She seemed really happy to talk to me and gave awesome eye contact. At the end of the meal, I told her I would take her to lunch if she showed me where she bought the bracelet. She said maybe, then proceeded to tell me where the shop was, then said thank you and took off.

I felt awkward after that, luckily I left about five minutes later. After all the other “cold approaches“ I don’t feel awkward at all, I feel great. What happened here?

My mother died when I was young, so I would really appreciate any feminine guidance on this issue. Male guidance is super appreciated too.

—————————————————-

Promised Positive Example: About a month ago, I went into the pharmacy to drop off a package I was shipping.

I took it in and looked for the first employee I could find, I heard a girl calling for me saying she would take care of it.

Up walks this gorgeous redhead. She must’ve been 22, long wavy hair past her shoulders, perfect body.

We say hi, we wait for another employee to bring the scanner. A man walks up and hands her the scanner then stands around. In a nasty tone, she tells him that what he’s looking for is somewhere else, I felt like she was trying to get him away from us.

When he was gone we we’re standing there for a minute, and I thought, then said following.

”I got a pretty big package”

Red: “I’ll make sure they can handle it.”

“Righteous”

She laughed, and said she loved that phrase.

It was at this point I know, I was in.

We stood there for a minute and I looked around to make sure no one was right next to us and I said:

“You’re pretty cute, you wanna hang out sometime?”

Red: I’m married. smiling But thank you, I appreciate that

“Respect. Have a good one”