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When I was in my early twenties one of my best friends, who was also in her early twenties, started dating a man who was creeping up on turning 40. It was right on the edge of socially acceptable but not exactly. Sure, when you say someone in her twenties and someone in his thirties are together, it doesn’t sound so odd. But when you consider that one was just a year out of college, barely yet able to pay her own bills, and the other had already owned his own company for nearly a decade and had friends who were nearing their fiftieth birthday, things start to look a bit different. We tried to all be good sports about accepting this much older man into our group but there was no denying that it felt a bit odd to all of us. Here’s what it’s like when your good friend dates a much older man.
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Your hangouts are slumming it for him
You can sense him turning his nose up at your group’s favorite spots. He doesn’t want to go to a crowded bar with sticky floors for taco Tuesday or a dingy spot for karaoke that sells Jell-O shots. You can sense that he’s uncomfortable there and just tolerating it.
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So he tries to treat you all at his spots
As a compromise, the older boyfriend offers to treat you all to drinks at his favorite spot. It’s swanky. Drinks are $15 each. He says he wants to pay for you all. You all resist but he’s so pushy about it. He clearly will do anything to not go back to your preferred dive bar.
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But your younger partners feel weird about it
The men in your group—like your boyfriend and the other boyfriends or husbands of your friends—feel very weird about this older beau paying for them. They’re men and they have pride. They want to pay for their partners. But they also can’t afford this $15-drink place. It always causes some awkwardness and resentment.
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You feel like there’s a parent in the room
You can’t help but feel that there’s a parent in the room when this man is in the room. Your friend acts like it’s normal, and wants you all to treat him as just one of the gang. But you inevitably tense up and watch your behavior, just like you did as a teen when a parent was around.
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So you feel weird about getting drunk
You can’t help but feel weird about getting a bit drunk around him. You can’t help but feel that he’s judging you all and thinking that you act young. But you are young. You don’t like feeling bad about that.
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You feel weird about acting juvenile at all
In general, you feel weird being yourselves when this guy is around. You can’t let loose. Whatever it is the younger members of your crew like to do—maybe the guys like to air hump each other on the dance floor—you feel you can’t when this older man is there.
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You wonder if she’s having some meltdown
You also can’t help but wonder if your friend is having some sort of an episode. Should you ask if she’s okay? If this dating-an-older-man thing is just a symptom of some emotional problem? Are you supposed to just sit back and assume it’s healthy?
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You can’t shake the feeling he’s a cradle robber
You struggle to gain full respect for the guy. At the end of the day, he has gray hairs and your friend still shops at Forever 21. Isn’t he a bit of a cradle robber?
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You also worry about their future
You naturally worry about your friend’s future. You know she wants kids. You know she wants to get married. What if this man has already been divorced and married? Or he already has kids? Will he do it all again with your friend? Or if he won’t, and your friend says that’s okay, is your friend just settling?
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References go over his head
References that you and the younger members of the friend group make go right over this older boyfriend’s head. You start to feel rude just discussing the things you would all normally discuss.
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You sense him trying really hard
You can feel him trying so hard to A) fit in and B) act like this age gap is no big deal. The harder he tries, the more apparent it is that this is, in fact, weird.
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Will she be his nurse one day?
You also worry that your friend will wind up spending some of her best years acting as a nurse to this man. He could easily start suffering declining health while she’s in her prime. So she’ll miss out on adventures and travel, to stay home and take care of him.
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You know how his friends’ wives feel
You just know that his friends’ wives roll their eyes at the situation. You feel bad for your friend, thinking about her walking into those dinner parties where she’s clearly 15 to 20 years younger than everyone there. You know all the other guests see this as a sugar baby situation.
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He can’t follow the riffs
Her boyfriend just can’t keep up with the riffs between you and your other friends. People of the same age group just speak the same language that people outside of that age group don’t speak. So, hangouts just aren’t as fluid when he’s around.
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Financial talks are awkward
Talking about money is hilariously awkward. He’s already had money in several investments for over a decade while the rest of you aren’t even really sure what a fixed asset is. Sometimes, talking to him about money feels more like taking a finance class from him.
