I Had an Unexpected “Hook Up” That Didn’t Quite Deliver. What We Did Instead Was Just as Much of a Delight.

How to Do It This seems promising. Aug 19, 202612:00 PM Photo illustration by Slate. Photo by Zoran Jesic/Getty Images Plus. Sign up for the Slatest to get the most insightful analysis, criticism, and advice out there, delivered to your inbox daily. How to Do It is Slate’s sex advice column. Have a question? Send it to Jessica and Rich here. It’s anonymous! Dear How to Do It, I had a wonderful, unexpected “hook up” with an old friend of mine last night. It was unexpected because we’d been platonic friends for so long and never thought “hooking up” was ever a possibility for us. For context, I’m a 52-year-old male, and she’s 50. So we’re both older and insecure in our bodies. (Ah, aging!) When we got to the hotel room, she became shy and didn’t want to remove her clothes. I told her that’s