Throughout the years, I’ve gotten pretty good at talking to women of all kinds. I’m not really afraid of small talk. I know how to banter pretty well, especially with more attractive women who are usually showered with compliments and validation, and consider myself a funny guy. Or so I’ve been told. I know not to overly obsess over their appearance or come on too strong too quickly. I know how to make myself stand out. I’m not the best looking, but I think my other qualities do compensate.

My main problem however, is knowing when the moment is right to escalate further when I have some sign of interest from her. I just freeze. There’s been multiple times where I’ve met a girl WAYY out of my league, we’ve hit it off, she’s given a slight sign of interest, I either miss that sign or pick up on it but don’t know how to act. As a result, her interest then fades and she gets with someone else. My opportunity vanishes. I miss my shot.

Like it just feels cringy to outright come out and be like “Hey I like you, wanna date?” Idk it just feels like there’s more to it than that. Should I gradually ease into facilitating more in person time together? What is the recommended sequence of events in this process? It’s honestly challenging enough as is to interpret a sign as actually being a “sign” that she’s interested in something other than a relationship. The last thing I want is to be labeled a creep and to have my name spread all over social media.

I can handle rejection just fine. It’s more so just knowing how to properly escalate beyond a friendship to begin with that I have a hard time figuring out. Any advice is greatly appreciated.