The Check, Please. Notable Observations on Dating & Friendship from Dinners with Friends. by Dish Stanley

Whenever I go out with a group these days I ask them to share tips or stories about how to check people out for dating and friendship at this stage. I’ve begun to compile a list of their trenchant and humorous observations.

"If he doesn’t floss his teeth every night, get out now."

This is, obviously dating advice. From a divorced woman who was married to somebody with bad teeth. "It’s about more than just bad personal hygiene — it’s a signal of somebody unwilling to make small investments now for their future health.“ More important at this stage than ever.

"If they make you wait repeatedly, it’s a sign that they’re self-absorbed."

From a friend who is married to somebody who always runs late. "I love her, and she is not selfish, but she is self-absorbed. There is a difference. I believe that people who routinely keep others waiting feel entitled to keep others waiting. Their lack of awareness or concern about *your* time may be less about an intentional desire to disrespect you, and more about their own entitlement or unconscious desire to exert control. I’m not talking about people who strategically show up at a cocktail party late or other examples where someone runs late but they’re not inconveniencing anybody. I’m not talking about the occasional instance of getting stuck in traffic unexpectedly. I am talking about consistent patterns. About things like you going to pick them up and they’re never ready … you meet for a walk and you’re always the one standing on the corner waiting for them to show up, you’re waiting to start the tennis round, etc."

Absolutely don’t marry somebody who grew up in a fancy New York City apartment building! Unless you’re going to live your life in a fancy New York City apartment building.”

From a girlfriend married to somebody who grew up in a luxe NYC apartment building with a great super.

"The building super - who made sure every little thing got magically fixed for them - is your worst enemy if YOU are not going to be living with them in a fancy New York City apartment building for the rest of your lives. They’re useless and clueless, and that job ends up as one of your jobs … “

Have a sharp take or story about subtle (or glaring) red flags in dating or friendship?

The Crush Letter
The Crush Letter is a weekly newsletter from Dish Stanley curating articles & intelligence on everything love & connection - friendship, romance, self-love, sex. If you’d like to take a look at some of our best stories go to Read Us. Want the Dish?