"Work" Jack meets Penelope (vendor visit). Jack wants to maybe try a date. Does Jack write from his work email or personal email to meet for lunch? Jack has her business card. Jack is unsure of her relationship status since he had minimal time for casual chat.
That can be weird because if you’ve only briefly chatted with someone you won’t know if they’re in a relationship (as you said) and you probably won’t know if they’re interested in you, either. A salesperson’s job is to be friendly and chatty, and a lot of people mistake that for flirtation.
Honestly, I think it would be best to see her in person a few more times to try to get a hold on the situation. Even then, give her a very easy way to back out without actually having to refuse because you don’t want to make her actual job difficult and uncomfortable. Something like, “I have drinks at Capote’s every Wednesday after work. Drinks are one me if you want to come by.” or whatever.
Honestly, I think it would be best to see her in person a few more times to try to get a hold on the situation. Even then, give her a very easy way to back out without actually having to refuse because you don’t want to make her actual job difficult and uncomfortable. Something like, “I have drinks at Capote’s every Wednesday after work. Drinks are one me if you want to come by.” or whatever.
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