Avoid Talking About Antique Dolls on a First Date: Dating Across the Generations

Penny, a woman in her early twenties, sits across from me with an intense expression on her face. “I’ve come to a realization,” she declares. “What’s that?” I ask. “I’ve decided I’m going to be single the rest of my life.” In the past year Penny had gone through a difficult breakup followed by a series of particularly painful first dates, including one man who explained in agonizing detail his collection of antique clown dolls.

Penny’s story is not unique. Singles are everywhere, whether a Generation Z attending high school dances or college parties, a Millennial perusing the post-ski happy hour scene, a Gen-Xer divorced with two kids (who has time to date?), a Baby Boomer searching the book/wine/supper club groups, or the Silent Generation facing widowhood and retirement homes. Regardless of age, singles cover a broad range of experiences. Some want a hookup or “friends with benefits” situation (STD rates continue to rise in nursing homes), while others want a special friend with no benefits: “Why can’t I find someone to go to the movies with on Friday night, or take to the family wedding?” Some singles want a knight in shining armor or a sugar mama, while others are looking for a life-long partner, marriage and possibly children.

The brutal truth is most people these days, from all generations, are finding partners on-line. Everyone is concerned about creepers (yes, as a woman you’ll get some frightening proposals), misrepresentations (how is this bald man in front of you the curly-haired man from his picture?), hurt feelings (I didn’t mean to insult his bi-racial mother), and overall exhaustion with the whole process (how many Starbucks lattes can I really drink?). But honestly, this is the most realistic way to meet dating goals.

So Penny decided to follow the standard steps. 1) Take a break from dating; go out with friends, visit family, pick up a new hobby. 2) Revise her profile and refine her search process (doll collectors need not apply). 3) Remind her community the type of partner she’s looking for and that she’s open to meeting their single friends. 4) Eventually, dive back in to dating with a little bit thicker skin, stronger sense of humor and trust in the long game.

Dating at any age brings challenges, heartache and disappointment, but also joy, excitement and hope. If you’ve been putting off diving in, choose one step and take it this week. It just might turn out to be worth it in the end!