Q: I’m a 50-year-old guy who’s been divorced for about a year. I’m beginning to date again, but I’m uncertain who pays for what. A friend tells me that he always pays for the first date when he goes out to dinner with someone new. But after that, he splits the check 50/50, unless there’s a special reason not to, like it’s her birthday. This sounds reasonable to me. But what should I do if, on the second date, the woman doesn’t reach for her wallet as I reach for mine? My friend says he just tells his date, “It looks like your share’s about $X” and hands her the bill. I’m not sure I’m that brave.
I sat for a while over the question, and deemed it an Alabama-essential question to answer.
Solution: First, you need to take a deep breath, and take this date number one gal out to a Burger King or local bar-b-q joint. Pool hall hamburger or bowl of chili would also be acceptable. The key emphasis here is that you you don't want to spend more than $15 (with the Cherry Coke or Pabst-Blue-Ribbon included) on BOTH of you. You pull out a crisp twenty-dollar bill (fresh, just ask the bank teller for new ones that came in) to pay entirely yourself. You want to demonstrate character, charm, and hospitality.
If things go south on this first date....you can figure it was a wise investment of the $15 and get over it quickly. Also, if she were to note that she was vegan or had some negativity about bar-b-q....it's good to get this out there quickly, and you can move on.
My brother would likely suggest that the catfish menu option would be a better choice, but then you'd be talking about $9.99 each, and $1.50 for the tea....going well over the $23 range. This would be the wrong move to show that you go out on the first date and splurge like that.
You should also take note how your date dressed for the dinner. If she shows up in fairly upscale clothing and $80 shoes....you might have tangled up with some high-maintenance gal. If she shows up in some $9 Wal-Mart football jersey and $10 loafers....you might have tangled up with some trailer-trash gal. Being observant on the first date is fairly important.
Finally, if by the end of the first date....you come to realize your gal carries around a Walther PPK 380 in her purse.....says she's got a better sauce recipe for ribs than the bar-b-q joint had....is open to going to wrestling matches....enjoys attending state fairs....and sips mostly micro-brewery beer for the taste-level, you'd best situate the 2nd, 3rd and 4th dates real quick.