Got a relationship problem? JASON GODFREY, our man about town, is here to help.

Portrait of Tammy Strobel

Got a relationship problem? JASON GODFREY, our man about town, is here to help.

My Reading Room
What are the best first-date questions you’ve had from women? I’m always stumped about what to say to my date.

“Why are you so awesome?” and “You must have a lot of women dating you because of aforementioned awesomeness?”. Actually, no one has asked me those, but I can dream. Just ask them questions about themselves, because (i) People like to talk about themselves, (ii) actually being interested in other people is a good skill to learn, and (iii) if they respond by talking about themselves, and never ask one question about you, you can figure out what kind of person they are and if they’re worth a second date.

I’m intent on settling down, but don’t want to scare men off by announcing this on a first date. What is a good way to signal my intentions early on without men thinking I’m creepy?

Most guys assume that women are intent on settling down. You have to make an announcement only if all you want is casual sex. What’s more important is learning to gauge how serious the guy is. Try to figure out what he wants – if all he’s into is drinks and booty calls, move on.

My Reading Room
I met a guy on Tinder. He’s based abroad, but we’ve been having hour-long phone calls every night for the past month. I’m positive we’re soulmates, but my girlfriends warn me I’m being presumptuous and should meet him in person first. Your thoughts?

The digital age is a precarious one for relationships. You can maintain close relationships online and may even forge new ones, but you will never know if you have an accurate grasp of his character until you meet face-to-face. And I really do mean face-to-face – when you can physically touch each other and smell the shampoo (or lack thereof) in each other’s hair.

My new boyfriend does not have any plans for us or himself for the future. My friends tell me that I’m being too uptight and I should just enjoy the dating process. Are my concerns unwarranted?

I’d like to say they are, but they’re not. Ambition, or a lack of it, can really affect a relationship. It doesn’t have to be about money and Trumping out at some point; it can just be about having passion. Does he have the drive to do anything? A skill that he likes to work on? Because we all need ambition, whether it’s to run a company, run for president, be the best father, or even work on a personal goal like becoming better at a sport. Life without any ambition is passionless – and nobody wants that in a relationship.