Old Pictures, Clownish Makeup, and the Unexplained Breakup

by A Dude

I have been in a wonderful relationship for about 10 months. My boyfriend is sweet, fashionable, loving, and basically everything you could ask for in a dude. (He bought me Prada sunglasses for my birthday without me even having to ask!) The sex is great, and I feel completely content with him, except for one thing…

We started dating a few months after he broke up with his ex-girlfriend, and they’d been dating for more than five years. I am usually very understanding about exes, so when he continued to make small talk with her every once in a while, I was totally cool with it. She lives halfway across the country, so I felt I had nothing to worry about. But then she got an internship in his town for the summer … Needless to say, they ended up sleeping together (we were dating for about two months at this point) and hanging out a lot. My boyfriend and I don’t live in the same town (going to different colleges about an hour and a half away), so I didn’t find out for a while. But when I did (through someone else), I was obviously very upset. However, I decided to forgive and forget, seeing as how I had had a few drunken flings during the first stages of our relationship. She moved away in August, and that was that.

Flash forward a few months: I help him move into a new place. I’m unpacking all his things for him, when I find a large collection of pictures of him and his ex (including one of her butt … seriously?). I confronted him about them in a very calm manner, and asked him if I could toss them out. He got very defensive about it, saying that he wanted to keep them for sentimental value and whatnot (he’s kind of a feminine dude, so it might be a legitimate answer). After that, about every month, I will find out that they’ve been talking, and he’s telling her he misses her, blah blah blah. Last month, I (accidentally!) saw a text message from him to her saying that he wanted to drive to her home and have sex with her. He says he was drunk and doesn’t remember it, but at this point, it doesn’t really matter; I’m still upset.

I love this dude, and I believe him when he tells me that he loves me. His ex has already moved on, but he still sleeps with the teddy bear that she gave him every night. I just don’t know what to do. What the heck is he thinking? Is this relationship hopeless? Help!

Ahh, the old, “I’m sentimentally attached to this photo of my ex’s ass.” You can’t imagine how many times I’ve said that.

I’ve gotta be honest with you: that part at the beginning of the question where you said you’re in a wonderful relationship … that’s not true. You’re in a relationship with a man who’s in love with another woman. You’re in a relationship with a man who has cheated on you (and whom you’ve cheated on?) and appears not just ready but eager to do so again. You’re in a relationship that strikes me as hopeless.

Even if this other woman lives halfway across the country and isn’t someone your boyfriend is in a realistic position to sleep with or date, you need to stand up for yourself and dump this guy. Use those new sunglasses that you love and no doubt look great in to go nab someone else. I’m intrigued to see if any of the gals in the comment section disagree with me, because I don’t really see how this is anything but an open-and-shut case.

However, before you go and dump his ass tout de suite, I wanted to ask: why the hell did you equate sentimental attachment with femininity? I fancy myself a guy’s guy but would charge head first into a burning building to save some crap I cherish dearly: my old baseball glove, a ring my grandfather gave me, a photo of my first dog that I’ve had since I was a child. He may be effeminate for other reasons (not that it matters if he is), but I just thought that was an odd connection.

We got trashed, you and me, Dude, last night on a really awesome date. Afterward we went back to my place, had great sex, and passed out. We’ve known each other for a little while, and everything is pretty good, but this is the first time you’ve slept over. Nice! Morning dawns, and there are lots of windows in my place, so we’re dealing with some serious natural light, and we basically made all my makeup go everywhere, so I’m looking kind of rough, but whatever, we’re adults. My skin isn’t perfect — old acne scars, tiny broken blood vessels — my eyeliner is smeared below my eyes like bags, and my mascara has gloriously settled into my crows’ feet. Holla at an incredibly beautiful woman. What do you think of this scenario? Does it seem clownish that women wear this much makeup? Is it kind of hot the way we made my makeup get that way? Is it gross? Does it not matter? To each his own, I know, but you, Dude. What are you thinking?

Well, between my headache (we got so trashed), morning wood, my desperate need for a cup of coffee and the glow I feel because I slept with this awesome gal last night, I’ve got a lot going on over here on my side of the bed. I’m probably a little too in my own head to notice any of these things. But even if I do happen to notice your smeared eyeliner or the tiniest little blemish, I honestly don’t care. This isn’t my first rodeo. When hungover the morning after, no one looks as put together as they did at dinner the night before.

By the way, you looked great last night, but remember that you also look sexy as hell right now. You’re probably not wearing that much clothing, and possibly wearing nothing at all. No headache in the world could keep me from noticing that. Point being, I love it when you get dressed up, but sometimes nothing is hotter than owning it in those intimate, disheveled moments.

Also, I don’t think it’s clownish that women wear that much makeup. Wear whatever amount of makeup you think you look best in, whether it be a lot or none at all.

I’ve been dating my boyfriend for three years, except for the three months (after the first year) when he broke up with me unexpectedly. He had seemed distant for around a month, and when I finally confronted him, he took a day to think about it and then ended it. Even though I confronted him, I never expected a break up — he was the one who initiated the first hook-up, the first “I love you,” the official relationship declaration.

I took the breakup really hard — it was the first time I had really been dumped. I wallowed, I lost weight, I acted slightly promiscuously, and then, I started to get my footing back.

Obviously, as soon as that happened, my ex wanted to get back together. I was reluctant at first, but after a year of thinking we were meant to be together, three months of uncertainty didn’t hold up long.

Here is my issue: after hours of talking and emailing (he travels a lot), he still cannot give a reason why he ended things. At times he has speculated that he felt pressure that all of his friends were getting engaged, but I’m several years younger than he is and wasn’t pushing, or even mentioning, marriage at all. I considered that he cheated, but it doesn’t seem like him, though during the breakup process, an explanation like another woman would have been a relief.

My worry is that if this happened once unexpectedly, what will keep it from happening again? He’s currently just as loving and caring as he was when we started dating, but that isn’t really comforting considering it didn’t stop him the last time. Am I being delusional for thinking it’s possible that he had a brain fart but is now capable of loving me long term? Also, a second question, do you think it’s an issue that I still worry about this? Should I have moved on already? I don’t bring it up often but it’s something I think about on a semi-regular basis.

I’m not going to speculate as to why he broke up with you the first time. (Not that you asked me to.) Unanticipated breakups during the first year or so of a relationship aren’t that uncommon and happen for all kinds of reasons, including ones that can be genuinely difficult to articulate. Admittedly “all my buddies were getting engaged” does kinda sound like bullshit, but honestly who the hell knows?

Point is, I don’t think it’s at all delusional for you to believe he’s capable of sticking by you. I know lots of people who broke up for a bit only to have a much stronger, lasting relationship the second time around. After three years together he’s going to be in a very different place emotionally than he was after one year, and he’s going to handle uncertainty differently.

But if it continues to bother you, then yes, I’d call it an issue. You do need to move on, but I don’t mean that in some callous, “get the hell over it” sense. I mean that you deserve to be confident that your guy isn’t going to bail on you. At a certain point the both of you need to talk about this in a substantive enough way that you’re brought some closure. It’s important that he realizes you’re still anxious about it. He may never provide a wholly satisfying answer as to why he broke up with you the first time around — such an answer just may not exist. But if he knows how much you think about it, maybe there are other ways he can double down on the care and affection in order to put your mind at ease.

I broke up with my reaaaalllly long term bf a few months ago, and I needed to make out with new dudes. Then I started making out with a new dude! The sex is great — I feel really comfortable with him, he has seemingly infinite patience dealing with my very frustrating body that doesn’t like to come; I believe him when he says whatever I want to do is okay, which is not something I’ve really ever believed from make-out buddies before.

The problem is that he really wants to date me. He wants me to sleep over all the time, even when it’s clear we don’t have time for sex, and he wants to do all these really sweet things for me and ask about my feelings, etc. I don’t want to date this guy. I want to have sex with him, preferably a lot, but I know pretty clearly that this is not someone I’m interested in having a serious thing with. I’ve never done the casual thing before, and I don’t know how the “can we just make out” conversation goes, and I kind of need to know how much of an asshole I am if I keep sleeping with him, knowing that I don’t want to date him and am sort of still looking for other people to make out with. Tell me?

Well, you aren’t an asshole for wanting to just have sex and keep it casual, because those things are great. But you need to be frank with him about the fact that this isn’t going anywhere. He sounds like a relatively emotionally mature dude. Look him in the eye, be honest, and, if he’s still down, hump like bunnies. At least one of your reasons for not wanting anything more (having just gotten out of a long-term relationship) is one that most anyone can sympathize with. Also, don’t have some overly serious conversation. That’s the kind of conversation a couple has. Keep it light and open, like you’d like your relationship (I’m using the term loosely) to be.

However, you’re not out of the woods entirely. The fact that he’s a sweet guy doesn’t mean he’s beyond doing something emotionally destructive like saying “that’s cool” even when he’s not okay with it. Despite our reputation, some men have a difficult time divorcing sex and emotion, myself included. If you get the impression that he just nodded his head and said yes because he’d say yes to anything that equates spending more time with you, I’d say you should break it off.

Some of my buddies would argue that if you were honest with him, you held up your end of the bargain, and the onus is on him not to play himself. But I just think it’s kinda crappy to be complicit in a situation that’s going to lead to someone getting hurt.

Previously: Age Differences, Irrational Jealousy, and the Haircut.

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 paul prescott, via Shutterstock