Encyclopedia of undatable men

In proverbs there is a time and a place for everything. In relationships there is a time and a price for everything. I don't ever like to cry poverty (except on my taxes). I make an honest living, and a very decent one with great benefits. I'm definitely not struggling and I have a great lifestyle. My cat and I live very comfortably. However, I have noticed a steep decline lately in the number of men willing to pay on the first date, and so my wallet has gone from guest star to starring role most of the time. If only to avoid the painfully awkward halfsies conversation. I want half and half in my coffee not on a first date. I suppose I could blame a lot of factors: recession, poor choice of both men and dinner locales, ordering one too many glasses of wine. But none of these seem to make any sense to me.

Last night was dinner with a doctor at Northwestern. Conversation was great, both of our five year plans line up conveniently (read: he was willing to say anything to make me happy), and we both like cats. And even though he's a pretty strict vegetarian he ordered the sirloin in what I can only assume was a play to impress me (a vegetarian ordering the most expensive steak on the menu, enough said). And granted his steak was smaller than a hockey puck and just as hard, and my rabbit was over breaded and fried into oblivion, I assumed given his twenty something years on me and position he would pay. The check came he looked it over and asked if I needed my bag.

"My bag?" I cocked my head slightly the way a dog would if you issued a command he'd never heard.

"Yeah, for your wallet."

"Oh, I keep it in my pocket."

"Okay, so half and half then?" he said throwing a card down. The bus boy dropped the pitcher of water, every old lady in Atwood Cafe clutched her pearls, the queens one table over gasped, even the business men in the corner lowered their heads over their Macallan twelve years, the music stopped, the waitress screeched to a halt in front of the table. I kept my calm though. It's how we compose ourselves in moments of tragedy such as this that really define us as people. I was calm because of my golden rule:

Zack's golden dating rule: Never order a dinner you can't pay for, even if you don't think you're paying for it. 

I always bring enough cash to cover for a bad tip and keep a credit card on hand when on dates. I assume they will pay but I'd never order a meal I couldn't pay for myself. When I was in college I had no money, so regardless of how sure I was the man would pay I only ever ordered salads because that's all I could afford. Now, I take myself out for dinners at Ralph Lauren and The Gage and I can pay my own way. And somehow it bugs me more now when I've got to reach into my wallet on a first date.

I took his card out of the check presenter and threw it back on the table.

"I got this," I said. The waitress seemed hesitant to take my card. She game me the "are you sure?" look. Although I was sure about paying I wasn't sure if there'd be a date two after this one. Let me elaborate on why with yet another entry into my encyclopedia of undatable men-- previous entries including "Triennial Man" and "Coffee Date Guy"

Pay-Your-Way Guy

A well-to-do "gentleman" in his forties that, despite being gainfully employed, doesn't like to pick up the tab due to being either a cheapskate, or simply dating too many men. Will always ask to go half and half. Your two choices are to embarrass him by just paying for the whole thing yourself or annoy him by asking to split the bill by item (a poor choice as this will undoubtedly annoy the waitstaff as well).

Immediately dump any man that makes you pay on your first date. Do not pass go, do not see a movie, do not talk to him about it. Just go home and eat ice cream. And if he asks to split the bill evenly, don’t walk, run out of there (after paying your tab). This rule only applies to the first couple dates and it’s not so much a money issue as it is an issue of him not doing everything in his power to win your affection. If he’s more worried about saving fifty bucks than he is about impressing you you’re better off with Ben & Jerry.

I do have a crackpot theory about the recent insurgence of these types as I believe for me the situation is case-speciffic.

I'm about to turn 25, and now that I have officially reached a quarter of a century nobody will ever pay for my dinner again. When I renew my driver's license it will no longer say "Starving college grad" because I've been out of school for three years now, make plenty of money, and live in a better neighborhood than most of the guys I'm dating (not the doctor, I maintain he was just cheap). I think the problem, if it could be called that, is that too many guys see me as an equal to them now. In some stupid way it's almost a compliment that a man in his forties would let me pay for his dinner.

No, I take it back that's still an insult on a first date.

Still, I can't help but wonder if becoming the independent and self sufficient person I am has caused me to lose one of the qualities I used to rely on in relationships, being the young broke starving artist/ ingenue with quick wit and a bright future. Now I'm the marginally successful widely ignored and un-renowned writer of a hip self-absorbed blog. Clearly I'm just far too successful and well off for these men to not consider me an equal. I mean, being as established as I am how can I expect otherwise?

I may just have to suck it up. Like it or not I'm an adult with a Visa card and it looks like I'm going to be seeing a lot more of it in the years to come.