This alone is a reason why I refuse to go back into the dating pool with guys my own age. When I’m out, the guys I seem to attract are generally in their mid- to late-30s. To find out why, I asked a straight twentysomething male friend, who pointed out that younger guys are simply intimidated.
After all, going up to a total stranger in a bar and making an impression isn’t easy, and it takes a certain amount of confidence, which often comes with age.
Persistence also takes confidence—my boyfriend extended three invitations before I finally agreed to get coffee with him.
As Aaliyah once said, “If at first you don’t succeed, dust yourself off and try again.” Older men know this. I won’t lie: It can be annoying at times dating someone who has “been there/done that,” but it can also be helpful when your partner can use his experiences to guide you.
Anyone who’s been in a serious long-term relationship knows the journey isn’t without certain challenges, and when you’re dating an older man—we’re talking a decade or more—things can get even trickier.