Mixed Signals, Mirrors, and Two Accidental May-Decembers

by A Dude

It’s December 21 and I need to break up with my boyfriend. If I wait until after Christmas/New Years, I seem like a mooch who just wanted presents (I don’t! I just don’t want to ruin his holiday!), but if I do it before Christmas won’t I just seem like a heartless bitch? I’ve needed to break up with my boyfriend since September … ok, MAY, but I’m having a really difficult time with it! I really do care about him, he’s a wonderful man, but I’m not in love with him and he does so many silly things that drive me batty. With other boyfriends I’ve just been brutally honest and called it a day — but I’ve been dating this guy for almost three years and he sees a future with me — I just don’t see one with him. I guess I can figure out how to go about it on my own (though if you have any tips to soften the blow, please share! I’ve tried to break up with him three times already and he just doesn’t get it). I’m really concerned about this delicate “it’s the holidays” situation. ACK! PLEASE HELP!

Okay so obviously, I’m more than a bit late responding to this one. ARGUABLY too late to help, and for that I’m sorry. But hopefully this advice might help someone in some far-off Christmas future. Maybe?

Anyway, I hope you dumped him. Even if it was on Christmas Eve, and you had to shout to be heard over the clatter of reindeer hooves. Let’s be honest, the idea that he might think you were only in it for the presents — can we both acknowledge that that’s a deeply unlikely conclusion?

He knows you. Has known you for at least three years. If you were in it for the lavish, opulent Christmas gifts, he would’ve sussed that out by now. And unless I’m missing something about how Christmas typically goes, nobody’s giving each other very good presents anyway. (Unless I AM missing something and other people are giving each other new cars with gigantic bows around them — in which case, please tell those people to date me and I’ll never, ever dump them.)

My suspicion here is that the Christmas thing is not the real thing. You’ve been wanting to break up with him since May! Seven months. To put that in math terms (not my strong suit) you’ve wanted to break up with him for nearly 20 percent of your relationship.

There’s always going to be a holiday. There’s never going to be a time when it’s super-convenient to dump someone. And, not to be all stern and exclamatory about this, but you can’t say you’ve tried to break up with him three times already and “he doesn’t get it!” It’s your job to make him get it! You can’t just let him hard-sell you into being in a relationship you don’t want. (Advice on how to actually enforce a breakup: probably a subject for another post.)

I think you’re stalling because dumping people sucks, especially when you care about said people. Plus it’s hard to end relationships that are just Not Good instead of Truly, Horribly Bad. But, as a dude who’s been in your boyfriend’s shoes, I guarantee you it’s so much better to get the news ASAP. Even if he doesn’t realize that now.

Nothing sucks worse than wondering afterward how long your ex was planning to dump you while you were completely in the dark. It’s embarassing and can make you suspicious in your next relationship. I also think that the time between when a relationship has basically died and when it actually ends is when both people tend to treat each other in the worst ways. If you haven’t already, please let the poor guy go before Valentine’s Day.

Hi dude. Dude, can you give me a reality check? I’m 32, and about 21 months ago I got my heart broken pretty badly, and have not really had a boyfriend since — until recently, sort of. I work for a large organization with different divisions, and this year I noticed a new face. A new and very very handsome face. LIke, tall dark and handsome and just . . . something about him that I liked. Anyway, long story short, I wondered about him for maybe two months whenever I saw him (not too often) until one day we were put into a meeting together, and afterwards he asked me out. We started dating, and the more I talked to him the more I realized he was probably younger than me. I asked, and he said that he was 27. Okay, a little on the young side, but not outside of possible in my book. I told him my age and he wasn’t fazed. I asked “doesn’t it bother you?” and he was like “ah, no.”

He’s very mature and smart and we had great chemistry. Then, after we slept together things began to feel kind of serious, and he tearfully confessed to me that, actually he was just an intern at our organization and (gasp!) not only that, but he had lied about his age and is only 23! I initially broke up with him, but he was so distraught and seemed genuinely sorry. He fought me a little on it saying “but come on, did I seem 23? did things seem strange?” and, actually, once he got that off his chest, he relaxed a LOT and I felt even closer to him. He seemed more himself somehow, which was still mature and “on my level” or whatever. I should also mention that he is GORGEOUS, attentive, seems emotionally sound, and communicates well. Also, he looks much older. My first guess was 30. He said he initially thought I was 26, then had upped it to 28 once we started dating and before I told him my age. Anyway, I really like him and he seems really into me and talks about how “rare” it is — both how great I am (he says) and how cool our connection is. Anyway I took him back. Yep. But due to some work things, it will have to be a long distance thing starting pretty soon. Because we both have the time now, we’re going to travel together for the next few weeks, maybe even as long as a month or more.

I don’t know, Dude — am I crazy to be getting involved with this guy? I want to get married and have children. Relatively soon. Plenty of guys are freaked out about this, at any age. But is it ridiculous of me to be dating a man nine years younger?Whenever I tell people, they automatically say “well, THAT can’t be serious.” But we’ve already decided we are in a committed relationship, at least for now. I wonder — what if I was 22 and knew I wanted to get married and have kids within three years? Would it be any different to date a guy who is 23? Is this really stupid? I didn’t mean to seek out a younger guy, and he didn’t realize how much older I was until we’d already gotten a little attached. So . . . what do I do?

Oh, dear. Just to lay out my credentials here, I am a dude in my mid-twenties who’s always tended to like girls who are a bit older than I am. So if you’re ever going to find an anonymous but sympathetic ear, it’s probably mine. I don’t think there’s anything foolish about you dating someone younger, and feeling feelings about him that are substantial and not just How Stella Got Her Groove Back-y.

And I get why he likes you, too. You’ve got a lot of what most people his age are still piecing together — a real job, a clear sense of what you want from life, furniture that doesn’t suck. To a younger dude, that’s really attractive. Plus, sometimes, dating a more mature person can help a younger dude (dudelet?) grow a little bit faster than he would otherwise.

That said, I would feel SO much better about this if you didn’t want this guy to father your offspring in the near-term. I know this isn’t the world’s most progressive thing to say, but he’s 23! He’s going to be, like, three or four different people in the next few years. Maybe some of them will want to be fathers. Maybe some of them could be good fathers. But what a risk to take!

(Granted: yeah, some dudes are ready to be dads at 23. Some of them aren’t delusional. But they’re a pretty rare breed. He could be one, but how sure are you that he is?)

Annnd, while you should eventually talk to him about where you’re at, wanting-to-have-a-baby-wise, I think it’s kind of worth noting that he’s shown a willingness to lie to you in order to get you to give him a shot. I know that lying about your age is, as far as lies go, relatively minor. But isn’t it possible that the same guy who was dishonest about his age might be dishonest in some other scenario? Like, for instance, if you were to say, “Hey — I’ve got a question for you about the future, and whatever you say is fine. But if you say no I’m going to stop sleeping with you.” Maybe that would be at time when he might maybe also shade the truth?

If I were you, I think I’d take this thing you guys have and enjoy it on its own (evolving) terms for a bit. Travel with him. See how the long-distance thing works. I’d table the baby-making stuff for now, with him, even if it’s just for six months.

I started hanging out with this guy over the past few weeks and I can’t tell if he’s into me or not. He “friended” me on Facebook and I recognized him as a frequent customer of the record store I work at, so I accepted even though we had never really talked about more than vinyl. He started chatting with me online a bit, which lead to texting, which lead to making plans to go see a band at a bar together. We stayed out late, drinking (neither of us was out of control — but I think it’s safe to say we were buzzed) and ended up going to his place to watch this movie we had been talking about and to have some coffee. We ended up falling asleep on the couch and then woke up in the middle of the night and moved to his bed. There was some snuggling and kissing, and as things were heating up I told him I didn’t “want this do be a one time thing” and he seemed cool with it and said that we should stop and just sleep. We stopped our make out session but the cuddling continued — which I thought was a good sign — and we fell back asleep.

Since that night we have continued to text and have got together a couple other times, but at the end of every hang it’s really awkward! He initiates getting together but at the same time makes it seem almost like he could take it or leave it. Also, because we mostly text, I don’t think he’s actually said my name ever, which makes me think he doesn’t know it — which is crazy, right? When we go out he makes no move to hug or kiss me goodbye even though earlier in the evening I’m totally feeling flirty vibes. He’s told me that he’s shy around new people, but it’s gotten to the point where I can’t tell if this guy is just shy and guarded or if he’s an asshole.

Part of my problem is that I (somewhat recently) came out of a serious relationship, so I haven’t been on a date in a long time. I’m worried that I’m reading the signals totally wrong. I also am worried that I might be blowing this out of proportion because I haven’t felt a connection remotely like this with anyone since my ex. I need your expert advice — do I wait it out, or do I get it together and ask him what’s going on?

You’re not reading his signals wrong, he’s just being kind of confusing.

If I’m hearing you right, you’re worried that he wanted to jump your bones but he doesn’t want to date you, and that you’ve scared him off by leveling with him. That’s one explanation for why he would’ve become noticeably more cagey after you told him you weren’t interested in a one night stand. It’s not the only explanation, but it’s possible. Alternately: maybe he just took you telling him to cool it a little bit too literally? Maybe he’s confused about how you feel, too?

To get to the bottom of this, you’ve just got to talk to him. You can only close-read text messages for so long. Put him in a bar, put a couple drinks in the both of you, and then tell him you like him and ask him how he feels.

Also — he has to know your name, right? You guys are Facebook friends.

Dude, do you guys make facial expressions in the mirror? Do you smile and fake-laugh to see how you look? We do that (I do that?), and I wonder if guys do, too. Do you take pictures of yourself on PhotoBooth and then delete them? Also how often do you weigh yourself?

Dudes are sneakier about this stuff, because male vanity is more goofy and unattractive (cf. Zoolander, late stage Axl Rose), but, uh, we do all of those things. Especially the PhotoBooth thing. I’ve caught friends. Another thing you left out: discovering and then worrying about weird, unflattering facial angles. At three-quarters profile, I look like a perfect hybrid between a neanderthal and a cartoon of a hillbilly.

I think the weighing yourself thing varies. I do it a few times a week. I’ll do it less when I’m gaining weight and don’t want to think about it. I used to think that I was part of a small group of covert dude weighers, but more and more I suspect that’s not the case. One piece of evidence is all those men’s magazines devoted to teaching dudes the finer points of eating disorders.

Previously: Old Pictures, Clownish Makeup, and the Unexplained Breakup.

A Dude is one of several rotating dudes who know everything. Do you have any questions for A Dude? (300 word max, please.)

Photo by Ragne Kabanova, via Shutterstock