While it's a bit of a stretch to think she'd say yes (yeah I know be confident yadayadayada) I have a lady I would like to ask out, think I have a shot wiith, and know doesn't have a date for Valentine's day. Is this a good time to try for a first date or does that add pressure that makes it a bad idea? I don't have a great track record on this so I have no clue myself. seeing as I have no reservations anywhere at this point, would I be able to set something up that could impress if she said yes? If I ask, should I set up a reservation first, and just cancel if she says no (see previous bracket if you think thats too negative)?
Any advice would be greatly appreciated, as I'm kind of a chickenshit and want to make sure when I ask this woman out, I've got my timing as right as I can.
Any advice would be greatly appreciated, as I'm kind of a chickenshit and want to make sure when I ask this woman out, I've got my timing as right as I can.

