While it is true that you don’t want to dwell too much on the sad things in life, at least not if you want to make a romantic connection, there’s not necessarily anything wrong with talking about real stuff… even on a first date. I had a GREAT first date a couple of years back. My date and I played a game called “Your Best Day.” It’s a good get-to-know-you game. You take turns talking about the best days of your life. Well, while it was bittersweet, the day when I gave my mom’s eulogy was one of my best days because I spent MONTHS writing a love letter to her memory. It was sad. But also special. And my dad and family were moved and got a lot of comfort from it. Sharing this story didn’t hurt the date (if anything, it made us closer) because we didn’t dwell on my mom’s death. Take-home message: If a personal subject comes up organically and you are in a good emotional place, feel free to get vulnerable. 

Connell Barrett is a dating coach with The League, founder of Dating Transformation, and author of the forthcoming book, Dating Sucks But You Don’t: The Modern Guy’s Guide to Total Confidence, Romantic Connection, and Finding the Perfect Partner.