Dr Date

Dr. Date,

The guy I’m currently seeing acts really strange about money.

He’s never shy to mention that he makes a decent salary, which bothers me. The weird thing is that he doesn’t really seem to be bragging, it just comes up in conversations in the same way that a vacation or a favorite TV show would.

Also, he’ll sometimes insist on buying the bar a round, but he usually appears to be fishing for compliments when doing so, instead of doing it because he wants to be nice or knows the people. He’s always insisting on paying for me when we go out, too, even when the outing was my suggestion.

But there’s a kicker. Behind closed doors, he’ll sometimes fret about bonuses at work and how much he’s got in the bank.

I know that he grew up in a poor family, so maybe that plays into it somehow.

How do I get him to calm down about his cash?

—Dollar Troubles


Mr. Moneybags,

Does he have a really ostentatious car? Does he wear flashy jewelry? Or is this not so much a matter of overt materialism?

Regardless of family background, this is an annoying practice. Anybody who waxes on about the prices of their possessions, their lavish fiscal situation or anything along those lines immediately sounds like a total tool.

I’ll tell you right now he’s not mentioning his salary just as some factoid — he’s bragging. (Or covering up for some deeper personal insecurity. Probably both.)

Unfortunately, we live in a world that prioritizes wealth — and it seems like he took that memo pretty seriously.

And hot darn, he whines about it behind closed doors? Does he have any redeeming qualities? This better be his only con in a laundry list of pros. Even if that’s the case, I’d lean toward dropping him.

—Dr. Date


Dr. Date,

My friend is a serial dater. Every time I see her, she’s got someone new on her arm. She seems to fall in and out of love on a whim. I can’t keep them straight. I love her and wouldn’t worry about it if it didn’t keep her in constant emotional fits.

She’ll call me one day ecstatic about her new beau, only to call the next day in tears because Johnny Generic didn’t text her back quickly enough.

She was like this in high school, but it seems with Tinder and all the online dating options, she’s getting worse and worse.

Is there anything I can do?



Concerned Friend,

I’m assuming there’s a swirling vortex of reasons for your friend’s behavior. 

The biggest of these is likely commitment. I’m going to guess that she either had one long-term relationship where she got the crap end of the stick or that she developed a fear of being hurt sometime in childhood.

But it sounds like she gets hurt anyway … and over the most benign relationship issues. This borderline irrationality is my biggest concern.

I’m intrigued by your social media theory. You think she’s being “enabled” by these applications?

I’d urge her to try her hardest to be single for a little bit, if only to have some time to clear her head without the interference of some random new “love.” If she’s all over her smartphone, similarly urge her to lay off for a sec and rediscover books or something.

If none of this sounds doable, sometimes the only option is to embrace the crazy and wait for her to figure it out.  

—Dr. Date