DEAR HARRIETTE: I work at a small bar, and I see a lot of customers every day. We have a group of regulars and some newbies. One regular comes in and always orders from me. We talk about his job and life, and after each of our conversations, I am more interested. He isn't married or in a relationship. I want to take charge and ask him out for a proper dinner, but I'm afraid he might deny me, creating awkwardness when he comes to the bar. Should I ask him out? How would you suggest I ask? -- Bashful Bartender, Las Vegas
DEAR BASHFUL BARTENDER: You are right to be a bit cautious here. Sometimes people share their life stories openly at a bar because it feels like a safe space in that there are no ties that bind. It is also true that true love has been discovered in that same setting. If you feel like the potential for a relationship with this man is worth the risk of awkwardness, go for it.
Tell your customer that you want to invite him to a “proper” dinner. Say that you like him and want to get to know him outside of the bar. State that you hope he will accept, but if he doesn’t think it’s a good idea, you hope the two of you can continue to be buddies at the bar. In this way, you will have given him an out if he needs one.
(Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to askharriette@harriettecole.com or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.)