Ask Logan: I’m Falling for a Guy 20 Years Older Than I Am

| 23.11.2017

I’m 23, and I’m very quickly falling for a guy who is 20 years older than me. We used to work together; he held the same job as my boss, but I was never his direct report. There’s always been chemistry between us, but now that I’m at a new company we’ve been meeting each other regularly as friends and the chemistry just grows each time. I think the only reason we’re holding back is because of the age difference. I know that’s a big consideration, but I think this relationship is worth it. Should I tell him I think we could be more than friends? And if so, am I dooming our future relationship or friendship for failure?

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Can a relationship work with an older guy? Yes. If you’re truly falling in love should you share your true feelings? Sure.

But, first, I’d pause and think this through. You say the “only reason we’re holding back is because of the age difference.” And it is a huge age difference, which will mean you are approaching your lives with hugely different sorts of expectations. (He probably doesn’t know how to use Snapchat, and he may think Cardi B is some kind of vitamin.)

But your career is tied up in this too, even if you work at different companies now. He’s a senior employee in your professional field and it sounds like you know each other’s colleagues. That’s not necessarily a problem, but you should be protective of your career—and aware of any risks. It’s a good thing to have friendly contacts in your industry—and a romance that fizzles could burn more than the friendship. It could burn a valuable professional relationship with a senior colleague, or potentially tarnish your reputation if it turns out you’re just his next lady. (I have no reason to believe that this guy is anything but sincere, but I have met quite a few forty year-olds who don’t have the purest of intentions when it comes to twentysomething women.)

My main advice would be to take it slow. Since he’s twenty years older than you, you’d be smart to be cautious, regardless. It’s possible to tell him you’ve got a crush on him without it ruining the relationship. If he doesn’t see you that way, odds are, he’ll just be flattered. I’d be more worried that the two of you hook up, and then it ends badly. If you do have the talk, talk in detail: Don’t just tell him you’re falling for him, make it clear that you’re interested in something serious and that you’d be hurt if he wasn’t looking for something real as well.

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My fiancé has a friend who keeps sending him nude photos and sexting him all the time. He always tells me about it, but it’s really bothering me and he doesn’t get it and I really want to punch this girl. We’re getting married in a few months and I don’t think this is ok. Is she trying to get him away from me?

I’ve got a wedding gift for your fiancé. It’s called the block button. I hope he learns to use it and love it.

My only other worry here is that you say she’s “a friend” of your fiancé. Frankly, it makes me question his judgment: If he hasn’t told this girl to lose his number, he’d better immediately tell her to stop wasting her time stripping down for selfies. Your boyfriend knows this bothers you and, for that reason alone, he should cut her off.

To be clear: I don’t blame you for wanting to punch this girl. You have a right to be angry. But don’t waste another second wondering why she’s doing it. Whether she’s trying to bait, taunt, tease, or seduce your boyfriend—or if she just thinks it’s funny—it doesn’t really matter. She just needs to stop because it’s not cool; it’s lame and disrespectful to you. And your fiancé should take care of it now because you don’t want to be dealing with this mess with your husband.

I’ve been dating my current boyfriend of a few months and everything is going great. We see eye to eye on many different issues and the mental connection is definitely there. But prior to him I had only slept with three other guys, and he, on the other hand, has slept with a few handfuls of girls. It doesn’t bother me because I understand the past is the past and that is where it should stay, but when we are having sex, that seems to be all I can think about. My mind is occupied with the thought of all these other girls and the fact that he might have had better sex than what I can provide. I know that I’m not bad in bed, I’m very open to trying new things, but now these thoughts have entered my mind and I feel like they are affecting my performance and in turn leaving me feeling disconnected. What can I do to fix this?

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I’ve got bad news for you: Jealousy never quite goes away. It’s a constant struggle for everybody. From middle school to the retirement home, from your first boyfriend to your last, you’re going to be jealous. Whether you’ve slept with one person or a thousand, you’re going to be jealous. At times, you’re going to think of who your partner has slept with—and, at other times, you’re going to obsess about it. And you’re going to have trouble getting your feelings under control. That doesn’t mean you’re a bad partner or a bad person. It doesn’t mean you’re crazy. It means your human: We get jealous because we care about someone so much we’re afraid to lose them. That’s actually a good thing.

So my first bit of advice is: Let yourself off the hook. Don’t double down on your jealousy with guilt. The guilt only makes it worse. Instead, look straight at the jealousy and see that it’s two things—an insecurity, and a distraction.

In terms of the insecurity, that’s never going to go away completely, but you can remind yourself that he chose to break up with all those other loser girls because they didn’t do it for him. He chose to be with you instead. He likes you. And, yes, he wants to have sex with you instead of them. Don’t get lost in the details. No matter who looks hot on Instagram, who he tells wistful stories about, or who he might have genuinely loved three years ago, he’s not with them now. It’s that simple: He’s dating you because he wants to date you. And he’s having sex with you because he wants to have sex with you. Not for any other reason. You are enough.

In terms of the distraction, whether it’s jealousy or the gravitational pull of your smartphone, it’s just hard to be in the moment. And it takes practice. Day by day, hour by hour, you’ve just got to recognize when you’re pulling away. Don’t get mad at yourself, and don’t label your jealousy “bad.” But take note of when you think you’re drifting. Look for the triggers that set you off. Try to focus on what you’ve got. Right now, you’ve got him and he’s got you. It sounds like you’re right where you want to be.

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