But, it's not all good things, as there’s also talk about their “bizarre” age gap: him 53, her 36.In fact, a Boston Globe report went a step further to chart Clooney's age difference history with previous girlfriends, the average being 9.73 years. But I've been watching and compiled a list of DOs and DON' Ts from Jess's experience dating the sophisticated Dermot Mulroney as Fancypants, who's a whopping twelve years older.Russell confesses he hasn't dated since 1989 and Jess replies, "That was the year I learned to use the toaster by myself." Not so hot.You didn't want to be with that guy who wanted an "outdoorsy girl" anyway. And he knows that vulvas don't usually look like two unused Pink Pearl erasers and smell like Bath and Body Works vanilla bean. Either way, older guys are more likely to be the most comfortable snuggle you've ever had.12. Have you ever seen an early-twentysomething guy get handed a baby?
Thankfully, most guys grow out of being the Leg Hair Police in their mid-20s. In his years of dating, he's probably been with a woman during a pregnancy scare and now fully understands the value of family planning.14.Attracting an Older Guy Maintaining a Healthy Relationship with an Older Guy Avoiding Hazards When Dating Older Men Community Q&A When you are 18 or above, dating an older guy can be an exciting challenge.While an older man will likely be more mature than the guys your own age, he’ll have an entirely different set of life experiences than you do.I know this firsthand, as I’m 25 years old, and I’ve been dating an older guy nearly 15 years my senior for almost four years.While you figure out the math, let me be clear that I’ve met several other women in their early- to mid-20s who also prefer to date from a much older pool for various reasons.