Most of the time it’s best to ask out a new girl without beating around the bush. “Do you want to hang out for a drink some time?” Yes? Okay great. But there are cases where you shouldn’t put yourself out there like that and need to feel around a bit more.
One good example is work. If there’s a girl you like (who I hope doesn’t work in your team/department), it’s best to find out (1) if she’s a drinker, and then (2) where she drinks at. It’s here you build some sort of commonality (“Oh I like going there too”) and then gauge her response for enthusiasm. High enthusiasm? Then you’ll probably get a yes if you ask her out.
Another example is at the gym. Virgle Kent wrote up a “How To Pick Up Girls At The Gym” piece and you’ll see that he attacks from an indirect angle. In both of these above cases you see the girl frequently and don’t want to make things awkward with a direct attack that doesn’t get the desired result. Uncomfortable vibrations follow.
I recently had to feel things out with this girl who worked at the Starbucks I frequented in Rio. It was my work sanctuary so I wanted to be careful about going hard and then getting rebuffed.
The girl gave me a lot of signs the first couple weeks, such as sitting at my table and chatting with me while she was on breaks. One day I told her about a champagne bar my roommate and I were going to later that night and how she should stop by for a glass (girls love champagne). She said yes and that we’d talk later but then she disapeared on me, leaving work before seeking me out.
Three weeks passed and while things weren’t awkward between us, our conversations were much shorter. I didn’t say anything about drinks again. When I only had ten days left in Rio I said, “Yeah my plan was to find a wife and get married to stay here but I failed. So now I have to leave.” She seemed genuinely upset and told me to write down my email address. Whatever, I thought. That night she added me on Facebook with the message “I found you.”
Should I ask her out again like I did last time? No. What I did instead was feel it out. Next time I saw her at the coffee shop she asked me how much longer I had left.
“Only seven days!” I said.
“Oh that’s too bad.”
“Yeah I’m getting ready. Buying some stuff, getting rid of books I’ve read. I probably won’t be here this week more than a couple times.”
“Are you going to come back?”
“Who knows. My only friend left last week though, and honestly I don’t even like the beach. :gay:”
“So what’s your work schedule like this week? You work every day?”
“Yeah every day except Sunday.”
“Oh that sucks.”
“But only until 6pm. I’m free at night.”
“Well if you want we can still grab drinks at that place I mentioned a while ago.”
“I’m free Thursday.”
“Thursday… that’s quinta-feira, right?”
“Yeah I can do Thursday.”
“Cool then I’ll have to get your number soon.” Then I grabbed my drink and found a table. I wanted her to feel anxious about when I was going to get it.
I danced around asking her out again until she put in enough effort that said, “You definitely should ask me out because I’m free to hang out with you.” This is an especially useful tactic on girls who have flaked on you in the past, because you don’t want to reward their behavior by asking them out over and over again. Unless it’s a straight-forward pickup like at a bar, club, or coffee shop (on a non-employee), it may be a good idea to feel it out to not only save face on girls who’ve dissed you before, but also avoid any potential awkwardness that may ruin spots you frequent. If she doesn’t take the bait by showing enthusiasm or availability, then forget it.