I’ve dated quite a few older guys and while they can be super cultured, financially stable, and generally really put-together, they tend to come with a lot of baggage too. Before you date someone who has more than a few years on you, consider these things.
He’s probably not going to party with your friends. He’s not going to hit up the bar every weekend with you and your single friends. Why would he? He’s already gone through that phase of his life. I’m not saying he’ll be lounging on the couch eating Hot Pockets every weeknight, but he probably won’t want to be out past 10 p.m.
He might still be a game player. Just because he’s older doesn’t mean he left his game playing ways in high school. One of the reasons he’s single is probably that he likes the chase. I’m not saying he’s playing you but if he’s “so perfect,” why hasn’t he been snatched up by now? Have you ever considered it’s because he doesn’t want to be tied down?
You’ll have to keep him young. Older guys are typically set in their ways. They’re not the most spontaneous, so you’re going to need to show him a thing or two to keep him young and in touch. Whether that’s playing different music or binge-watching a trendy show, it’ll be your responsibility to keep him from slipping into middle-aged man syndrome. Can you handle that responsibility?
He’s going to have a lot of ex-girlfriends. You might have one or two serious exes, but he’s going to have a ton. In fact, they might even be ex-wives rather than just ex-girlfriends. That doesn’t mean his exes are his best friends, but there’s a chance they might still be around and part of his life, especially if he has kids. Be prepared for a few awkward run-ins.
He might be a little too stable. Odds are, he’s going to be more stable than you are, which is probably why you’re attracted to him in the first place. Stability can be comforting, I get that. However, it can also make you feel bad about where you are in comparison.
He could be ready and looking for marriage. Is he ready to get married? Probably. Are you? Probably not. Not every older guy is looking for a wife, but it’s definitely a possibility. Ask questions before you get too caught up in this relationship and take your time.
He’ll (hopefully) be good in bed. With all the years he’s spent pleasuring vaginas, he should be good in bed. By now, he knows what works and what doesn’t which means you’re in for the ride of your life… but that ride might be controlled. Like I said, he knows what works and there’s a chance he might straight up tell you what you’re doing wrong.
He’ll provide you with insight. He’s already gone through what you’re currently going through and he survived. He can be the voice of reason for you on certain topics—sounds great, doesn’t it? There’s only one problem. He might unintentionally push you to make decisions that he made (or wish he made), kind of like your father.
He’s probably not that mature. Older doesn’t always mean wiser. Just because he’s older than you doesn’t mean you two have completely different interests. He probably watches cartoons on Sunday too. If you’re dating an older guy because you think he’s going to spend his weekends bidding on expensive art, you’re in for a rude awakening.
He’s going to be set in his ways. As someone who’s dated several older guys, I can confidently tell you they’re very set in their ways. It’s not their fault—they’ve had more life experience and because of that, they know what they want and what they don’t. You’ll be following their lead at every turn. Sound good?
People are definitely going to judge you. People are going to judge your relationship (to your face and behind your back). Sure, he might not look his age, but that doesn’t really matter. Once you tell people how old he is, they’re going to have opinions — especially your family. They’re going to ask why you want to be with someone that age and hopefully, you have a good answer.
You’re always going to feel like a child. Unless he’s the world’s most immature guy, you’re probably always going to feel like the child in this relationship. If you don’t mind being around someone who pushes you to be “more adult,” then dating this dude should be fine. If you’re easily intimidated, it probably won’t work.
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