On early dates, should I pay because I'm more able to afford it (which I usually will be), or should we split it to be equal?
For some quick background, I'm newly single and dating again. I generally use dating sites, which I'm very happy with since they've served me pretty well. (Understatement.)
I know there have been past AskMe questions about who should pick up the check. (1
.) Those are interesting but not directly responsive to my question.
Here's the deal. For most of my past relationships, we would split the bill. This was when we were both
students and/or struggling to get by financially, so it wouldn't have made much sense for one person to do all the paying.
In the past couple years, as I've switched from being a student to being a professional, my income has gone way up, and I make more than most people. Not quite six figures, but close. (This is in the US.)
Based on experience, I rarely end up on a date with someone who makes more money than I do. She is most likely my age or younger, and the odds seem pretty low that she's making a comfortably middle-class salary. (I'm completely open to dating women who are older and/or make as much or more than me, but I'm just generalizing based on experience and for the sake of this question.)
In my last relationship, we went Dutch on the first few dates because I like to establish equality as a basic guiding principle. But after we became official, I always paid unless there was a special occasion like my birthday or something.
Now that I'm back on the market, I'm wondering if I've been using the best strategy or if there's a better way to handle this awkward issue -- particularly on early (first, second, third...) dates.
My thinking is that I should pay when it makes more financial sense from a gender-neutral point of view
, which will usually be the case. The upsides of this are pretty obvious: direct financial upside for her; I don't much care about the financial cost for me; and she might be pleased.
But there's a downside to this, which is that she could interpret it as traditional gender stereotyping: "I'm the man so I pay for you." I don't want to present myself that way. Frankly, it makes me cringe. I also don't like the idea of setting a precedent (in the event things do develop into a real relationship) that our interactions are going to be unequal just because I'm the man and she's the woman.
I've never been convinced that I should pay in order to succeed with more women, because here's the thing: even if 90% of women want the man to pay, and 10% prefer things to be equal, then I'm probably most interested in those latter 10% because they share my values.
I know someone is going to say: "The rule is that whoever asks the other person out should pay," but I don't find this to be much guidance.
It's often pretty ambiguous who "asked" who. The "let's get together" issue just naturally comes up when you're using dating sites. I also don't like making a big deal about how I asked you out and therefore I'm calling the shots and paying for everything. And realistically, I'd feel foolish letting her to pay for both of us anytime she happened to suggest the date.
If/when a real relationship develops, I'm quite comfortable openly talking about the fact that it makes more sense for me to pay for most stuff as this actually levels the playing field. But I'd rather not bring this up explicitly on early dates. I don't want to be all, "Well, since I make a lot more money than you..." And I also don't want to launch into an extemporaneous treatise on gender relations in the middle of a date. (I actually did discuss this on a recent first date and it actually went over well, but I'd also worry that some women could find this offensive.)
(Since I know that people sometimes research an asker's posting history, I should mention that I'm using a sockpuppet because I'd rather not attach my name to something talking about my salary and dating practices.)