Meet Joel, our resident dating expert. He’s no Tony Robbins. He won’t ask you to pay a zillion bucks to attend his seminars. He’ll just tell it like it is, from the wise POV of someone who’s out there dating — just like you! Ask Joel “What’s the Deal” or anything else.

Post your questions/comments to Joel in the comments section below. 

Dear Joel,
What’s the Deal?!?

This guy I really liked from work asked me out. I got all excited but on our first date he took me to Buca di Beppo and asked if we could split the bill. I don’t want to be a jerk but that kind of bummed me out! He’s so cute and sweet though… I don’t know what to do?

—Split Decision

Dear Split Decision,
Here’s the Deal:

First off, I would be very careful about dating someone from work. Dating within the workplace can be tricky if things don’t work out and you are forced to see the person every day. Even if things do work out, job competition, rank and seeing each other 24/7 can inject unneeded stress into the relationship. Don’t you watch Mad Men?

As far as splitting the bill, it all depends on your perspective. Would you rather he ask that you pay? I have been on first dates where I offer to pay and the woman I am with wants to split it. Is the subtext that she doesn’t want to owe me anything? Is it a post-feminist way of saying “we are equals” and “I don’t need a man to provide for me?” I have come to the conclusion that in order to not risk offending someone I offer to pay, and then agree to whatever she counters. 

The good news for you is that chivalry isn’t dead. But in today’s dating world it’s a bonus, not an expectation. Maybe your dude got chastised for offering to pay on his last date? If he is cute and sweet, then don’t make a big deal of this. As you two get closer, just ask him about it. If things go well, you’ll be joking about it a few months down the line, and you won’t believe you made such a big deal out of it. And when he’s in the bathroom you can go into his wallet and reimburse yourself for the date. Just kidding.


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