Wait, did you purposely mean for this to be the worst advice ever? No that would be this gem from another thread: I would recommend that you invite the girl on a double date. Just talk with one of your male friends who has a potential date he could bring, and mention to him that you'd like to try to get together on Saturday at noon (or Friday at 8pm or whenever) for lunch followed by home made ice cream cones at Stone Bros. in Annapolis Harbor, where the four of you can walk around and talk and watch the boats dock. If it's chilly, offer her your jacket. After your friend talks with his potential date and finds out that she's free on Saturday, then you can call or ask the girl that's obviously interested in you if she'd like to join "Bill and Sandy" -- or whoever your friend and his date are -- on Saturday for lunch and ice cream cones. She wouldn't feel as intimidated as she might otherwise if it were just the two of you -- having a group makes it easier on you guys because the girls will be talking to each other for a lot of the time, and you'll be talking to your guy friend, but the important thing is that you'll be hanging out with this girl and getting to know her better and showing her that you're a nice guy who's interested in her. Good luck and let us know how it goes! Second date: the movies. Yes, I know... trite, banal and hackneyed, but... it's safe because you won't be forced to make constant conversation with her. I think he's out to sabotage single SF men.