Lose the labels
Whether it's attaching what-does-it-mean anxiety to certain acts, shaming a woman for sleeping with you too soon, or thinking you don't have "game" if she doesn't, there are a lot of labels surrounding sex that can complicate an otherwise great night together. "I used to think doing certain things in bed were not masculine or that a woman was defined by how early she slept with me," says Chad, 35. "As a grown man, I realize that all of that was just a bunch of nonsense brought about by insecurity and overthinking."
It's better to wait for sex than push
Fact: when a woman wants to have sex, she'll give you clues. You don't need to ask for it, make aggressive jokes, or offer envelope-pushing commentary to test her boundaries. In fact, taking an in-your-face approach will likely work against you. "When I was younger, it was all about getting her to go home with me," says Marcus, 42. "Nowadays, it's more exciting to build things up and have her completely comfortable and happy to be there with me than to be doing it because she's drunk -- or worse, feels obligated."