Tinder Mercies

I'm a successful lawyer in my late 40s doing online dating. I'm active in the Republican Party and philanthropic causes, so I often go to benefit dinners, for which I typically buy two tickets in advance. I've asked two women I met online to come to these as a first date, but both canceled by text at the last minute. (The dinner yesterday was $1,000 a plate and for a political cause that means a lot to me.) Maybe I'm just attracting rude women, but I'm beginning to wonder whether I'm doing something wrong.

--Empty Chairs

You can learn a lot about a woman on the first date -- like that she still hasn't worked out her drinking problem and that she doesn't always like to wear panties. Ideally, you find these things out while seated across from her at Starbucks, and not after she climbs on the table at a benefit and starts doing some sort of fertility dance with the centerpiece. Sure, it seems convenient when your need for a plus-one coincides with your desire to go on a first date with some online hottie. But you're better off coming up with a list of attractive female friends you can take or even male friends who share your politics or just enjoy free meals enough to not challenge your tablemates to a duel over theirs. Not taking a woman you barely know is also an important business safeguard -- so that when some conservative client of yours turns to your date and asks "So how do you two know each other?" he won't hear something like, "We met in the 'Republicans Who Like Hot Wax Play' chat room on Christian Mingle."