Ask the Expert: Dynamic Dating Profiles’ Kathleen Donohue on Dating Etiquette

By: Kathleen Donohue

Hey singles, I’m Kathleen, profile writer and editor at Dynamic Dating Profiles. I’m here to answer your questions on how to navigate the sometimes murky waters of online dating. In my line of work, I do a lot of listening, and as you might imagine, I’ve heard some horror stories. Here’s one that resulted in a very uncomfortable situation, a crushing migraine and a quick end to a budding relationship. And it all could have been avoided with better understanding, and frankly, better manners.  If you can top this one, I’d love to hear from you. You may just see your letter in this space!

Those First Few Dates: Who Pays?

Dear Kathleen,

I’m a woman in my fifties, divorced six years. I’ve been dating online for over four years now, and I keep running into the same problem. Who should pick up the check? I just stopped seeing someone I thought was a great guy over this issue!  And by the way, I‘m not one of those women who expect the guy to pick up the tab all the time. The first few dates were fine; we both paid for our own coffee, etc. I was really getting to like this guy. Then he calls and says he’s got a big surprise for me. He takes me to the coliseum, and I’m excited—is it a concert? A hockey game? When we get to the ticket window, I see the signs—OMG, it’s a monster truck rally. But that’s not the worst part. As he’s buying the tickets, he turns to me and says, “It’s $18 a ticket.” I was too stunned to do anything but fish around in my purse for a twenty. I spent the next two hours assaulted by deafening engine noise and diesel fumes—and paid for the privilege of a splitting headache. Afterwards, he genuinely seemed perplexed that I didn’t invite him in. He called me to ask me out the next day and I said, “I don’t think so.” He still had no clue. Why are some guys so cheap?

Carolyn S., Cincinnati, OH

Oh, boy. That must have been an especially embarrassing moment at the ticket window. But it could have been so entertaining for those in line behind you if you’d said, “YOU invite ME to a flippin’ tractor pull and you’re not even buying the tickets? Didn’t your mother teach you any manners?”

Here’s the rule, folks. I don’t care if you’re male or female, 18 or 88, if YOU do the inviting, YOU do the paying. Or at least try to (some gallant gents simply cannot let a woman pay, and will wrest the check out of your hands, but at least you made the attempt).

I’m not talking about established relationships; in those cases, I still think you should take turns unless one of you way out-earns the other (and even then, the one who earns less should occasionally offer, and always express gratitude). I’m talking about that dicey, getting-to-know-you phase, where one misstep can quash a budding relationship. How do you navigate this treacherous terrain without appearing like a cheap-skate?

Let’s talk about that all-important first meet-up. Of course it’s only fair that you should both pay, but it’s still awkward when the check comes. I know a woman who will simply not see a man for a second date if he doesn’t grab the check. That’s her first barometer for thinning the herd, I suppose. I think that’s a bit antiquated, and she may have missed out on a generous guy who may simply not want to offend a “liberated woman” by playing gender stereotypes.

Here’s what I do: I always reach for the check. Always. I do this as a human being, not as a female on a potential date. Nine times out of ten, he does too. Somehow, to me, if feels better to scuffle a little over the check than to whip out the calculator and say, “Yours comes to $11.63.”

I will say this: I find generosity very attractive. And, I enjoy BEING generous. It makes me feel good. I don’t think I’m alone in that. When it comes to attracting the opposite sex, ask yourself this question: when has stinginess ever been attractive? Has Ebenezer Scrooge ever been called a Hottie? This isn’t a gender thing, or even a wealth thing. It’s about being willing to share what you have with someone else. If you can’t open your coin purse a crack, how are you ever going to open your heart?

I will also say this: if the guy doesn’t reach for that first check when I do, I don’t assume he’s a tightwad. Maybe he’s new at this, and his bitterly divorced best friend warned him against gold diggers. Maybe he’s afraid of offending a modern woman. Maybe he’s nervous and just waited a half-second too long. I would never judge anyone by what they do at this perilous moment. But next time out, I’d better see at least an attempt at a check-grab or he’s going to start looking… cheap.

I understand that, in this day and age of so-called gender equality, it’s tough for men to know what to do. Women are as perfectly able to buy themselves dinner, drinks, and a movie as the guys are and often more so. But there’s something unseemly about standing to the side, pretending you’re not uncomfortable whilst your date buys their own ticket. Definitely a turn-off.  To me, it says, “We’re not together. You’re on your own.”

So how about this, ladies and gents: let’s all treat each other. Sometimes you’ll be the treater, sometimes the treatee. It’ll all even out in the wash.