Simon Says, Volume 2

Who pays on a date? Time to train your boss? A booty call or love? Ask Simon, our stylish English purveyor of “spot on” advice.


Alessandro Guerriero/ 123RF Photo

Who Pays on a Date?

Dear Simon,

I’ve been out with a woman three times over the last month. We have great chemistry, and despite the fact that I only make $45,000 a year, I’ve paid for everything. In total, I’ve spent $350, with the third date being breakfast (after the second date), at which she also ordered lunch to take home. She thanked me and said she would pick up the tab on the next date. But when we went out, she was only willing to split the check. When I protested, she scowled and said, “What am I, your sugar mama?!” Do guys have to pay all the time? —Pinching Pennies in Playa

I hate to have to break it to you, but I’m afraid the answer is yes, guys do have to pay all the time. And I’m afraid earning “only” $45,000 a year is no excuse. It’s not just because your ability as a breadwinner is one of the crucial things women look for in a mate, but also because your generosity toward a woman tells her that you value her. It’s not the dollar amount, it’s the gesture.

In return, you have to decide whether she is worth the outlay. From what you have written, it sounds as though you spent the night together after your second date, after which you decided she wasn’t worth a doggy-bagged lunch. If that’s the case, then either you’re the kind of guy who clips the coupons or she was boring in bed.

But given that you kept an account running until the next date, I’m going to give her the benefit of the doubt.

Time to Train Your Boss?

Dear Simon,

Every time there’s a project due on Monday morning — necessitating working over the weekend — guess who gets the assignment? Maybe I’m being paranoid, but I don’t think so. My boss just assumes that because I am single, I don’t have a life! He seems to have a double standard for my married co-workers. What’s the best way to take back my weekends? —Worker Bee

It’s the nature of business to demand ever more from workers, and it’s the nature of bosses to follow the path of least resistance to meet their goals. In your case, your bosses are very likely choosing you because they know your co-workers’ spouses — like their own spouses — are tougher than the Teamsters when their partners are asked to do overtime. You might not win every time, but you can battle with the best of them by using your own line of least resistance: Make sure you have plans for the weekend. Nonrefundable tickets to a game or concert, a promise to nurse an ailing relative, dinner plans with a friend from out of town. You get the picture.

When it seems that you’ve been the dumping ground once too often, pull out that secret weapon. When you do accept the weekend of work, make sure you get credit. And then ask for a huge pay raise at the first opportunity.

Booty Call or Something More?

Dear Simon,

I broke up with my fiancé three months ago. We both realized it was just never going to work out. The only place we really got along was in the sack — in fact, it was the best sex I’ve ever had. I’m starting to date again, but I’m in no rush to get into another relationship. He’s been asking me to come over for a visit and I know we’ll end up sleeping together if I do. Would it be OK to see him just for booty calls, as long as we’re both clear on the rules? —Tempted

We may come close to having a female president, but those old double standards still apply when it comes to dating. Any girl still getting it on with her ex is liable to be branded with a scarlet S if she’s also pursuing new love interests — not to mention the fact that you’re putting a major roadblock in the way of any serious future romance.

However, what I’m reading between the lines here is that your relationship with your ex is not truly over. If it was, you’d be looking forward, not back.

Copyright © Simon Says / 2015 Singular Communications, LLC.

Have a question for Simon that you’d like to see answered in Singular magazine? You can reach Simon at

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