Aside from a nightclub, I see the most attractive women while I’m on the subway or bus. A close second is when I’m just walking around the city, especially in Manhattan. Every city has a district that is more upscale, and attracts women for shopping and food. This is the best place to meet women during the day. But let’s say you are running errands, and she is running errands. How do you break the ice?
Far and away the best way to meet a woman during the day is by complimenting them on something they are wearing or doing. You can tell her you like her hair, her dress, or just that she looks cute. After she says “Thank you,” just ask her what she’s up to. Tell her what you are doing and then ask her about her life – where is she from, what does she do for work/school, and what does she do for fun.
After a couple minutes of small talk, tell her you’d like to see her again, and hand her your phone. If she says she has a boyfriend, tell her to take your number down in case anything changes, and, “Feel free to pass my number on to any cute girlfriends. I’m single so I’m open to meeting people.” She’ll respect this.
Being curious about her conveys your interest, in a way that is relaxing and charming. If she’s reading, ask her how her book is. A really simple question is, “Hey, how are you?” This may seem like strange behavior, which is why she’ll “get it.” Strangers don’t normally walk up to each other and say this, and because you chose to approach her, a pretty 20-something, instead of the old guy on the other side of you, she’ll understand that you are interested. If she is cold, it’s likely that she has a boyfriend or is not interested in meeting anyone. If she smiles and talks to you, she is probably available.
It may seem corny, but asking for directions, even if you know where you’re going, is great because it gives you a way to segue into talking about yourself – what you’re doing, where you’re from (if you’re asking for directions, you are probably new to the city or from another area) – and then you can ask her about herself. Boom, you’re in a conversation.
4. Go Direct
Sometimes you only have a small window of time to talk to her. She is getting off the train or bus, and heading home. The doors are about to close. Do you get off and chase her down? First ask yourself, “Will I regret not trying?” If the answer is yes, get off your ass, get moving, and don’t be afraid to make a fool of yourself. She’ll find it flattering and charming, and if she gives you her number, you can bet it will be solid.