Hi everyone, disclaimer here is you are dealing with probably one of the most inept daters on this planet, clueless is word that describes me well.

Short story is I have have know this person for a while, we have mixed in large social groups, she is more extrovert than me, I am more of an introvert and somewhat shy at times. She had a bf, I am single, she broke up with her bf recently and being in large groups its difficult to socialize but I ran into her at an cocktail party last week and we had some one on one time and I really enjoyed her company.

There was quite a lot of positive body language from her, granted there was a moderate amount of wine involved and full disclosure we have had two business meetings before this. What I enjoyed was the conversation, I do not mind admitting I am very fussy about dating, there is a very certain sort of person I find attractive and rather unexpectedly she proved to be attractive (granted she is very physically attractive too)

The evening ended with what I would refer was a firm hug and “lets do coffee”.

Next day I send her a msg saying how nice it was to see her and lets do coffee, 4 days later I get a response and it seems its not been defined as a “business” coffee.

Am I wasting my time trying to progress this, oddly I had such a nice time with her because I felt some sort of connection which is VERY rare for me. My great weakness is generally feeling like anyone I find attractive is out of my league and I am a lesser person, on line dating and my inability to attract people I find attractive has probably re enforced this.

Flirting is not my strong point and I am wondering how far out of my comfort zone do I go here? I am very aware that this has not worked well for me before but again I am reminded I did feel connection.

What would you do?