Dater X: Taking Turns, Investing Equally

This week, I found myself in a position with Scar Twin that I’ve never been in before (and no, I’m not talking about sexual positions— that’s a story for another day). Anyway, as many of you know, my last long-term relationship ended about four years ago when Patrick Bateman decided to have two girlfriends and two lives in two different states. Since then, I’ve found myself on an endless carousel ride of courtships lasting approximately two months each before things turn to shit. During those short-lived romances, the issue of money never really came up. And then, this week, it did.

When I start seeing someone new, being treated to drinks or dinner usually indicates to me that the guy is willing to put his best foot forward and woo me. I always, ALWAYS offer to pay, but rarely am I ever taken up on it. And quite honestly, if any new guy I’m dating did suggest we go dutch or expect me to pay on the first couple of dates, it would leave a bad taste in my mouth. Luckily (or maybe not so luckily?), I’ve never gotten to the point in a relationship where money needed to be discussed.

I’ve been seeing Scar Twin now for almost two months, and things are progressing at a healthy, steady pace. We’re in a good place. We usually see each other several times a week and have established a level of comfort and ease that I haven’t reached with most of the other guys I’ve dated. To put things in perspective, on a scale of one to super comfortable, we’re, like, a step above talking about my period, and a step below open admission of having to poop. Anyway, Scar Twin has always paid the bills on our dates, occasionally allowing me to pay the tip or for after-dinner drinks. I’ve never taken his generosity for granted, especially because we’ve gone to several restaurants that are on the nicer side. I’m not talking suit-and-tie places, but you know … nice. Recently, he finally accepted my offer to give him some money toward my meal after we dined at a fairly swanky bistro in my town, per my recommendation. Then, this week, he suggested he make us a reservation for a romantic, yummy restaurant with a great view that he thought I might like. It wasn’t overly expensive, but it wasn’t your run-of-the-mill pub food either. When the check finally came, he took it and put down his credit card. As usual, I took out my wallet and offered to help.

“Thank you for offering, but I got it,” he said. “And we haven’t really talked about it at all, but would you feel comfortable alternating who pays from now on? Like, I’ll get this one, you can get the next, and so on?”

“Absolutely,” I said. “That’s totally fine.” And it is! But having never been asked that question before, I didn’t really know what to think of it. Is that customary behavior after a few months of dating? Even though I’ve always offered, should I have been insisting on paying all along? For having dated so many dudes in the last few years, I’ve never once been faced with this scenario. So, after spending the night at his place, I went home the next morning and called my brutally honest mom to ask her opinion about the whole money thing.

“I think that’s a great sign!” she said. “You know he’s not cheap, but he’s being conscious about how much money he’s spending, which is good. He’s thinking ahead and knows he wants to continue seeing and doing things with you, but consistently paying for two people to go out each week gets expensive. It’s 2014 and I think asking you this after a few months is totally acceptable.”

She had a point. I put myself in his shoes and realized just how much money he’s probably spent already, just in the last two months, and it’s A LOT. Like him, I also have a job and bills to pay, so why shouldn’t I be contributing more regularly, especially now that we’re past the point of “newly dating”? Money doesn’t grow on trees, and while he does have a great job, I know how expensive it is to be an adult. Rent, mortgages, student loans, car payments, medical bills: they can suck you dry, and I don’t want dating me to be a part of that list. Looking back, initiating that conversation speaks to Scar Twin’s maturity level, and shows me that he’s comfortable enough to bring up a touchy subject in a tasteful, respectful way. He’s comfortable enough with me to communicate his wants and needs, and sees me as an equal in our relationship. I see this discussion as a positive thing, but am I right to assume that this is a step in the right direction?