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Drunk Pics, Hot Sisters, and Long-Distance Dumping

1. Here’s my situation. I’m a successful, attractive 30-year-old woman who has recently (like just signed papers recently) gotten out of a painful albeit short marriage (together three years, married for one and a half). My marriage was neglectful for some time, and it took therapy and a lot of work to realize the problem wasn’t me, and I feel like I have been handling things pretty well.

I had been lonely and emotionally unfulfilled in my marriage for a while. I rushed the engagement probably to hold on to someone who wasn’t that into me. I feel like I have been grieving for a long time. I left because I wanted the RIGHT relationship, because mine was so screwed up and one-sided. And now I realize that marriage isn’t the end-all I fantasized about, but I do want a partner and eventually a family. 

When I finally moved out, I started a profile on a dating site because I was utterly depressed and wanted to look at pictures of cute boys to help me get over my loss. Since it was my first foray into those sites, I didn’t realize I would be bombarded with people who were basically just DTF… but there was one guy that struck up a convo about non-dating, non-relationshippy things and we had a nice back and forth message chain for a while. Then we started texting, and then finally, he asked me to hang out with a group of friends. 

I managed expectations and was afraid the verbal chemistry wouldn’t be there, or that he would be less cute in real life. Neither of these things were the case and we ended up hanging out later that night and just BOOM SLEPT TOGETHER. Spent the next day together too. We get along well, have a lot of things in common, and crack each other up.


In the meantime, I am getting side-eye from friends and my mother about me even talking to dudes, and lots of WAIT FOREVER BEFORE YOU DO ANYTHING, so I cannot imagine how things would play out if they knew I was dating someone. Operative word DATING. I have no desire to move in together or otherwise link up in a major life commitment way right now, but I want to spend time with this person.

We have had the ‘taking it slow’ talk, but the truth is, I don’t really know what that means. I mean, I don’t want to hang out every day because I want to attend to myself and enjoy life as a single-ish lady but I also would really love some companionship and affection from a man, especially one I like. I understand the people around me are not just being busybodies, but rather probably just protective of me after all that has transpired … and don’t want me with The Wrong Dude. 

Anyway, I need to find the balance. He’s patient, which is great, and has a life of his own, but we’re in the talking-all-the-time mode and I don’t want to just stop! Plus we hit it off in bed, so halting all further carnal activities is not something I want. How can I be careful with my heart/boundaries while still enjoying the company of someone I like? HALP.

A very similar situation just happened with a close friend of mine who is a dude. In fact it’s so similar I hope you’re not his ex wife who I’m obliged to detest. You’re probably not! So I’ll tell you what I told him.

You can’t fight a vibe. I mean, you can, I suppose, but taking things slowly when the vibe is right is like trying to speed things up when you don’t hit it off. It’s unrealistic and not possible unless one or both of you are unbalanced weirdos. On the other hand, we can experience VERY INTENSE vibes when they are NOT HEALTHY at all. Hitting it off with someone can have as much to do with the relief they give from old, bad feelings as it can with him being the right dude. Your friends and family seem to think you are not ready to tell the difference. 

Which is what I asked my friend a few weeks ago. If, when you sit quietly with yourself and close your eyes and think about this new guy, what really comes up? If your heart feels truly free and at ease about this new relationship, then go for it. Really. I am only saying this because you said you went through a lot of therapy and worked on yourself, so I’m taking your word for it on that. Only you know if you are really ready. Just don’t take for granted that you are simply because you want to be. Really listen to your gut.

It’s important that you listen closely, because like I said before, you can’t control the pace or depth of this new entanglement. So rather than worry about that, just be sure you’re ready to ride this thing out no matter where it goes.

2. I organized a camping trip for my birthday. My friends drove long distances, the lovely (older) man who I’m dating came out — and dropped some CASH on snacks and booze — and we had delicious dinner and swam and everyone was having a grand time. There was music. There was a birthday cake. Really lovely, magical times. Until I got drunk. And then I was falling over. And then I was the butt of all of the jokes, rightfully, and then I went to bed. And in the morning, I was not hungover, but I did feel that kind of shame-clench that was exacerbated when the lovely older man pulled out his phone and showed a picture to everyone of me on the ground being drunk. And all of my friends laughed and laughed, and I was kind of like “ha-ha” … poker face.

I am emerging from several years of bad-drunk tendencies. I have a therapist, we talk about depression and anxiety and booze and sex. I haven’t been drinking so much for a few months, and then, this weekend, something kind of flipped and I boarded the bus to Dark, Baby Land without even knowing that that was what I was doing. But I can process this stuff with my therapist. The part that’s really fucking me up is the dude. We haven’t talked much about our previous lives and loves. I’ve not wanted to because I think it’s more … fair? … to take someone on their current terms, but now I find myself in this gross spot where I backslid, and I don’t know how much I need or want to explain.

He was affectionate on the way home. We talked on the phone after I dropped him off. We have plans this week. I apologized to him via e-mail for being such a weirdo on the night when he met all of my friends for the first time, and thanked him for being so generous. But, I don’t know what to do next, with him or with myself. I showed him my worst when he was really showing me his best. And yet …

What’s up with showing off that picture? What’s up with taking it? He’s 20 years my senior, and I’m in my 30s, and that was totally rude, right? Or, am I so affronted because I’m sensitive about drinking and outside commentary on the way I drank because DUDE, I’M WORKING ON IT!!!? I can’t tell how much import to put on all of this. I can’t tell how ashamed of myself to be. I can’t tell how much of an asshole he was being.

This is what we call a red flag. And it’s the exact kind of red flag that most of us ignore in order to keep dating the “lovely” person we are dating.

Not all red flags are the same, in that some are across-the-board red flags and some are personally subjective red flags. Across-the-board red flags are things like violence, straight up verbal abuse, and thinking Malcolm Gladwell is a genius. You know, obvious monster shit.

Your red flag is personal to you. It is one simply because you feel it is one. What your guy did, in my opinion, is possibly quite funny and fine. But he didn’t do it to me with my friends. He did it to you with yours, and it really bothers you. So it IS fucked up. To you. You need to say that to him. If he says, “Oh my God I’m so sorry I had no idea drinking and falling down wasn’t hilarious to you, I feel terrible, let’s discuss your past a little so we can get to know each other better bit by bit until we are in love” then maybe the flag is an opportunity to repair and become closer through mutual understanding.

But if he’s like, “Whoa! C’mon, that’s what phones are for, drunky!” Then he’s not necessarily wrong, but probably wrong for you.

Also, he’s 50 something and still taking drunk pics and laughing about them? Either he’s super cool and comfortable with himself, or he’s completely terrible. Either way, good luck!

3. Help! This just happened. Is it ever appropriate for a guy to mention that he finds his girlfriend’s sister attractive when in conversation with both ladies? (Some logistics: I’m 24, my boyfriend is 24, my little sis is 20.) My initial instinct was that some unwritten rule of dating had been violated, but maybe I’m being a little irrationally insecure — she’s definitely “the cute one” of the siblings, and knows how to work it, so I’m increasingly threatened by her in romantic territory. (I guess that makes me “the neurotic one.”) The bf is somewhat aware of this sensitivity. 

My thoughts: Clearly he’s into me, because he’s dating me, and of course he’s going to discreetly check out my sister because that’s what guys do, but I never want to hear about how he’s kinda into her as well, even jokingly over drinks. … Too much?

PS: Haven’t confronted BF about this yet, because I can’t decided if this response is on-target or wildly out of line with your typical sane and self-assured lady.

Of course it’s inappropriate for your boyfriend to comment on your sister. Also, of course he did it in the first place because he’s 24. Aaand of course you should say something to him. Most 24-year-old guys have a lot of growing up to do before they can sustain a healthy relationship. You telling him how insensitive it was to do that is pretty much the only way he’s going to learn it. I do not envy the heavy lifting required in dating dudes in their 20s, because there are so many battles to fight if you want them to become men. You should do the grooming in good faith that if you stay together, he may one day be a charming and thoughtful, mature partner for you. And if you break up down the line, you’ve still contributed to improving the dude pool for other ladies. Hopefully, there’s a guy out there getting reprimanded for staring at the wrong butt right now, and when you meet him in five years, you won’t have to tell him to keep his eyes off your sister.

 4. So, I’m in a three-year-long relationship, and, unfortunately, the time has come to end it. We’ve been long-distance for a while and will be long-distance for a while more, and I just can’t do it anymore. I’m exhausted. I haven’t gotten enough from him emotionally/commitment-wise to make it feel worth it, and I feel taken for granted. Nothing is seriously wrong, but nothing is seriously right, and I just can’t hack it anymore. I’m very broken up about it, but I guess that’s just the way the cookie crumbles, right?

Anyway, my problem is this: When do I break up with him? He’s coming to visit soon, and we haven’t seen each other in quite some time; we’ve been very excited about the visit, and now I feel like a total ass. Do I break up with him before the visit and feel terrible he spent $500 for nothing? Do I wait and hope that everything resolves itself during the visit? And if it doesn’t, do I just pretend everything’s okay and then at the airport be like “ummmm so I think we should see other people, this week has been great, k bye?” I know there’s no good way to break up with someone, but all of these ways seem particularly messy. 

Ask a Dude, it really hurts me to have to end this relationship; my guy hasn’t been the perfect boyfriend, but he’s been pretty darn good, and I want this to be as painless for all parties involved as possible. I love him very much and I know he loves me, and this whole thing is just one sucky mess of irreconcilable differences. Blergh. Help!

End it now. I was in a similar thing many years ago, and I let the lady travel across the country for an already scheduled visit because I thought she should hear it in person. She ended up leaving four hours after getting there — leaving on a train to the airport in the pouring rain and crying so hard I thought she was going to barf. I remember how sad she was about the break up in general, but I REALLY remember how mad she was that I let her travel all that way just to break her heart in person.

Breaking up with this guy over the phone does not make you a bad person, and doing it in person does not make it not a break up. Save him the time, the travel, and maybe some of the money.

Previously: Hair and Morality.

A Dude is one of several rotating Dudes. Do you have a question for A Dude?



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