Miss Information: I Fell For An Older Woman

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How do I convince her I'm serious, despite my youth?

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Dear Miss Info,

I'm a twenty-three-year-old man. After I came out of a fairly intense relationship last October, I've spent the last year exploring London and meeting lots of interesting people. I haven't really been looking for a relationship, but I'm not looking for casual sex, either — I mainly enjoy getting to know people better, and sex just happens to be a fairly awesome way to spend time with someone you like. Since October, I've been seeing two or three people at any one time. This had worked pretty well, and, as long as I'm honest and up-front about it (and I try to be), I didn't see any particular reason to feel guilty about it. 

Then I met this fairly awesome woman. We seem able to be open with each other in ways that neither of us find possible with most of the other people in our lives. The issue is, she's thirty-one. I'm totally fine with this. But she's only ever had relationships with older men, and, while she does like me, I think she feels a little bit guilty for "taking advantage of a youth." She also wonders whether this is sensible long-term, and whether she shouldn't be finding someone to settle down with.

The other thing is that, up until now, her dating life has been almost entirely long-term relationships. She doesn't "do" casual sex, and finds my recent approach to dating slightly bizarre, if not downright deviant. 

I do like her and would be quite willing to move into something more serious and exclusive eventually. (We're not there yet, but I can see that happening.) So what can I do to ease her doubts about my age, and her worries that she's just "another name on my list," without making things too heavy in the short term while we get to know each other better?

— Totally Over Younger Booty Only, Yucks


I love the acronym, and love even more that the best "y" word you could come up with was "yucks." I'm additionally going to interpret "yucks" as "old-tyme lolz," which I think brings a vaudeville quality to this letter. Kid, you'll be a star!

I may sound like a vulgar Hallmark card here, but seriously: age ain't shit. When you say "I'm twenty-three," a person files you in their mental folder marked "twenty-three." They compare you, then, to themselves at twenty-three, their bratty brother, their out-on-bail cousin, or their little sister. They make a whole set of assumptions about how you must understand the world and how prepared you must be to make a commitment.

Of course, these assumptions aren't necessarily accurate: one twenty-three-year-old may possess the gravitas of George Clooney, while another may smash beer cans on his forehead. She probably fears that you're in a place where you want to push boundaries and screw around — those wild oats, you know — and she's afraid of getting hurt. So age is an easy shorthand, a way for her to discount your preparedness and make herself feel better. If things go downhill, she can say, "Well, I should have known better than to rob that cradle."

As she gets to know you, though, she'll start replacing those age stereotypes with actual facts about you, and age should become less of an issue. The "seeing other people" part is tricky, because, in the early days of any relationship — until you say otherwise — it's generally assumed that either party could be dating around. If you want to reassure her, make sure she feels like a priority. If she's still uncomfortable with you seeing other girls, as the relationship progresses, you can adjust. But in the short term, show her you care the way you would show anyone: make an effort to see her and let her know how much you enjoy spending time together.

Ultimately, every relationship is going to have that awkward stage where both parties size each other up: "Is he too tall?" "Is she too talkative?" "Oh God, is that a Scientology decoder ring?" This is no different. All in all, I think you're on the right track. Just give it some time to see how things shake out.


Dear Miss Information,

I adore my boyfriend. We have heaps of fun together, support and love each other, get along with each other's families, and are wonderfully GGG. I'm twenty-six and he's thirty-four. We've been together for two-and-a-half years and I thought we were ready to move in together. Last year, he was kind enough to let both me and my roommate stay with him while we looked for an apartment. We called it our "trial run" and it went great. Now, my lease is about to be up on my apartment, and we have some decisions to make. 

I had just assumed we'd move in together when my lease was up, but he's having second thoughts. He thinks it's too soon and he likes his space and he wants to just go with the flow and take it easy, la la la. He says we've got our whole lives, so why rush into anything?

I, however, am sort of an anxious person. I'm the one with the lease, I'm the one who'll have to find another apartment, I'm the one with a roommate/BFF to take into consideration. I feel like my lease ending is a deadline, and I keep thinking, "If he's not ready now, how do I know he'll be?" I've told him all this and he's been as supportive as he can, but I still feel crappy. And I can't keep obsessing and feeling shitty and rejected over this, because that's not helping anyone. So where's the line between putting pressure on him and asserting what I need? Am I overreacting?  

— Frustrated and Feeling Stupid

Dear Frustrated and Feeling Stupid,

Moving brings the crazies out in full force. The last time I moved, I spent two weeks word-vomiting to strangers, braiding my hair while humming to myself on the subway, and buying Doritos in bulk. I don't even eat Doritos normally. Am I proud? No. But it happened and we need to move on.

My point is that the stress of moving affects everything in your life, no matter how minor. You can hardly be blamed for feeling rejected and hurt. But I think that if your boyfriend says he's not ready, you should pay attention. Moving in together prematurely can cause the kind of relationship meltdown that requires a U-Haul to remedy. It's a big step, and if he has even slight misgivings about it, give him his space. Forcing the issue would only intensify stress for both of you.

You already have a BFF and built-in roommate, so it seems like you have the best possible Plan B in place. Throw yourself into finding a place that you both love, with the understanding that you might not be there for the duration of the lease. Once your immediate living crisis is taken care of, you will be in a stable place to re-evaluate the situation with your boyfriend. Maybe you can set a time limit, and agree to revisit the issue in six months or a year. But for now, I would recommend drawing a clear separation between "moving stress" and "relationship." Otherwise you may wake up one morning fully-dressed in a bed full of chips, and wonder where it all went wrong. Hypothetically.