A friend and I used to have a game we would play in bars. Basically, we would take turns picking people and she would try and get them to buy her a drink.
The catch is that they would also have to buy me a drink, too. If you picked someone and they didn’t buy you a drink, then you had to pay for a round of drinks.
It seems simple, but it was actually deceptively complex. You had to pick someone who looked like they would be dumb enough to buy a woman and a random dude a drink, but since it would be mean to immediately tell them to fuck off, you had to pick someone who wouldn’t be terrible to drink with. Even if you won the pick, if they were terrible and we had to ditch them and go to another bar, you had to buy the first round at the next bar.
Picking the bar was also part of the game. If you picked a bar and had absolutely no luck, then you had to buy the drinks at the next bar until someone agreed to pay for drinks. For my part, I chose bars I knew would be frequented by college students, because college students are dumb and horny.
My tactic, which I kept to myself, was to pick bars close to Columbia, because there was a better chance of finding someone with money, and since it was Columbia, it went without saying that they’d be dumb.
To the best of my recollection, the only time she didn’t eventually get someone to buy us drinks was when she tried to get cute and turn the tables by going to a gay bar and making me get someone to buy us drinks. While I did try my best to get drinks, I think gay guys were just generally too smart to do something stupid like buying a drink for a guy and his opposite gendered friend.
I have had women pay for my drinks, but I still don’t think I could have swung getting them to pay for someone else’s too, so we never even tried it.
Recently I was talking on the phone with this friend. She told me how she usually plans on having a glass of wine or two with dinner, but most nights ends up drinking at least one bottle of wine and then going to sleep. She asked me, in a very uncharacteristically candid and serious way, if I thought she was an alcoholic. I avoided giving a straight answer by saying that I do the same.
I went to visit her for a week. Rather than going out to bars and trying to get people to buy us drinks, we spent most nights in her house, drinking three-to-four bottles of wine and playing chess. Getting old sucks.