Reason 539 Why Dating is Rough: Check, Please!

Recently, a certain vertically gifted gentleman and I were catching up over email, and of course the conversation wandered on over to our love lives. He was recounting the various twists and turns he’s currently experiencing when he wrote this (quoted with permission and name changed btw):

“On Thursday I went out with Jennifer (who my friend met at her second cousin's wake). Guess what? I bought two rounds of drinks (as is proper form), but Jennifer neither said thank you nor offered to buy a round. Guess that's how she rolls. Is that weird that I think that's weird? It seems petty on one hand, but strange on the other.”

Upon reading his email I was struck by déjà vu. I just had this conversation not too long ago, but from the opposite viewpoint. A girlfriend of mine had just come home from a first date she had been extremely excited about. The rapport had been great, the signs all good. But then, out of nowhere, I get a text: “I’m done with him – He made me PAY!”

Huh. First dates are so god damn rough. There’s opportunity for fatal error with every word uttered, and I think all of us can probably recount a first date where the evening took a sudden sharp left turn from promising to “well, this was great, but I gotta get up real early….” From “Woo hoo!” to “Uh oh…” From a strong heart beat and good prognosis to flat-lined and morgue-bound. As Wise Cassie recently posted for her gchat status (presumably after a first date), first dates “are like job interviews, except with cocktails.”

Dear God, how do recovering alcoholics and Mormons get through them?

Added to the confusion is this whole “Who picks up the tab?” minefield dance that goes down just as the date is rounding third. As seen from the two aforementioned examples, a perfectly good evening can go down the tubes if this spot is handled incorrectly by either party. A budding relationship nipped in said bud. Good times, but no happy ending. We no longer live in the world of Mad Men when the rules of engagement on this topic were so crystal clear: Boy asks girl on date. Boy pays for date. Girl bats eyelashes, smiles, says thank you, and goes home hoping a marriage proposal is next. This day and age, playing a quick mental game of WWDD (What Would the Drapers Do?) does not a clear answer give.

I don’t know a lot about dating. In fact, some could say I’m the last person that should be handing out advice. This particular spot, however, I do feel as though I have mastered and can execute flawlessly every time. That being said, allow me to recommend a few guidelines for both sexes on how to successfully navigate this oh-so-precarious spot. (a.k.a. “How shit should go down”)

Section 1: “The Main Tab”

Note: The term “Main Tab” is somewhat self explanatory and refers to the main event of the date, usually the meal tab, not including tip.

Guys, as a rule of thumb, know that you are on the hook for paying for the Main Tab at least for Dates One and Two. That being said, pick somewhere you can afford. We’re not looking for you to wipe out your bank account; we’re simply looking to be courted and made to feel special. Plus, it’s cringingly nails down a chalkboard awkward for us if there’s even the whisper of a wince when you see the total. So if pizza by the slice is all you can manage at this juncture, then slices all around. Just be sure to hunt down the best slices in the city.

Normally, I’d like to say Date Three is where it’s acceptable to let the lady pick up a Main Tab, but by all means, if you are aiming to send a strong WOO message, go for it. Think of it as Extra Credit. Please know that if you cruise past Date Four without allowing the lady to treat, you are conditioning her to expect you to treat at all times from now until eternity. Do not, then, get your panties all up in a bunch when after two years of dating her and picking up the Main Tab each time, your lady stops even reaching for the check. You did it to yourself. (Woops, how did that piece of baggage slip into this conversation??)

One you’re past the initial chunk of dates, I think it’s perfectly acceptable to alternate who foots the bill, especially if both parties are gainfully employed professionals. It is never, ever, under any circumstances, in my humble opinion, acceptable to go “dutch”, no matter how long you’ve been together. Nothing kills the romance quicker than the look the waitress gives you when you ask her to “split it between both cards….”

Section 2: “The Secondary Tabs”

The person who has just been treated should now seek out a Secondary Tab to pay for as a gesture of gratitude and reciprocity. This could be as simple as offering to leave the tip at the restaurant (see below suggested script), or to grab the next round of drinks. Or it could be to pick up the next activity on the date: the movie tickets, dessert at a neighborhood ice cream shop, a round or two of ammo… You know, whatever. Whether or not your date chooses to take you up on this offer is immaterial. As you can see from the account my gentleman friend gives, it is the attempt that matters.

Section 3: “It’s the first date, and the check has arrived: A suggested script”:

Scene: The check has arrived. It’s sitting on the edge of the table in the little black sleeve. No one has touched it; the tab is not known. Lighthearted conversation is still bouncing back and forth, as if a time bomb has not been just placed six inches away. However, all mental energy on the part of both parties is now focused on how to navigate the next five minutes. Assuming both diners are even somewhat interested in a repeat of the evening, may I suggest something similar to this:

Man – picks up and looks at the check. Places credit card in folder and closes it, if possible without even pausing in what he’s saying.

Woman – in a timid voice, gesturing towards the closed folder, “Can I help with that?”

Man – “Oh absolutely not. I’ve got that covered.” Smile, showing teeth.

Woman – Show surprise and slightly exaggerated gratitude. “Oh! Thank you so much – that’s so sweet of you!” Touch his arm here, if at all possible. “Perhaps… I could leave the tip?” (Note to women – Always carry enough cash in the right increments to make this easy if he says yes.)

Man – You have two choices. You can either say, “Um, well, ok! Let’s see, looks like $15 should be plenty.” OR you can say, “Nah, I’ve got it covered. Thanks, though. Why don’t you grab us a round of drinks at this great bar down the street.”

See how easy this can be? No muss, no fuss.

I’ve been told the average male dreads this moment during a first date, because he is presented with a potential lose-lose situation. In this age of female empowerment, his date may get offended if he won’t accept her money. On the flip side he may be labeled cheap if he does, as was the case of the guy with whom my girlfriend dined. Upon further review of that particular play, however, a blunder on her part became evident. The bill came, and he picked it up. She offered to chip in, and he declined. Instead of thanking him, though, she went around the bend one more round, asking if he was sure. He froze in panic and then after a long pause finally blurted out, “Err, fine. Why don’t you just give me a twenty?” Yikes.

Don’t worry, fella’s, she’s got the script down now. We’ve rehearsed it several times.

Now, if only the rest of dating could be this easy…..

Buyin’ the movie tickets,

khop