The other night I was out with a big group of friends at a bar and having a good time chatting with the guys. Soon two women joined our group and situated themselves at the end of the table, they were both cute and one in particular caught my eye. Her eyes even lit up when she overheard that I was a good cook.
I knew I wanted to talk with her, so after I excused myself to use the bathroom, I came back, pulled up a seat at the end of the table and simply said, "Hey, I wanted to see how the other side of the table was doing." After introducing myself to everyone I sat next to the girl I was into.
We talked about her life in law school, what I do, and cracked jokes about everything from TV shows to our backgrounds. It was a great, flirty conversation. I even caught a buddy giving me a thumbs up from the other end of the table.
If I'm meeting a girl for the first time, I prefer to not just get her number, but make loose plans for our next date. We talked about how much we liked eating gourmet cupcakes and she mentioned a bakery I'd never heard of. I suggested we check it out and she was interested. I let that germ of an idea marinate, and chatted about other things.
After an hour and a half of conversation, with not just her but the friends around us as well, she casually mentioned, "Yes! That is funny about that site. My boyfriend is now good friends with the roommate he found on craigslist."
I was shocked, but played it cool. A buddy of mine was heading out the door, so I excused myself to bid him farewell and to reflect on this new bit of information from the girl. He was completely surprised to find out this girl had a boyfriend after she had been blatantly flirting with me for over an hour.
I would hope women would mention, very simply, if they are in relationships. They could do this by saying how they had a great dinner with their boyfriend the other night within the first 15 minutes of conversation.
But no, women like male attention, and understand that mentioning that they are in a serious relationship while a guy is flirting with them will soon end the interaction.
Guys, we have to be proactive about finding out this information, so that we don't waste an hour or more of time like I did. I like small talk, but if I'm chatting one-on-one with a girl in a non-business setting .... I'm interested in dating her! Obvious, right?
I'm not a fan of bluntly asking, "Are you single?" as it puts an awkward strain on the conversation. Instead, I prefer to indirectly find out if she has a man like this:
Me: "I just went to a great Italian restaurant the other weekend. What's your favorite place to go out for dinner?"
Her: "This Chinese place in my neighborhood."
Me: "Sounds tasty, but you gotta go out and try this Italian place. You and your boyfriend should check it out."
Her (if she's taken): "Yeah, we will check it out!"
Her (if she's single): "I don't have a boyfriend."
And then we'll talk about something else. She'll know what I was "really asking," but will usually smile because it's a question that conveys your interest in her.
So remember: Find out within 15 minutes if she's taken and do it smoothly.