Questionably Tattooed Manchildren and New Uses for Old Jars

by A Dude

So, here’s a question you guys probs get all the time, but I have to ask it because there is a crazy hamster in my brain who will just. not. get. off. the. wheel.

I am a pretty good-looking lady of 33 years. I like sex, I’m funny, I have plenty of friends, I own my house. I have a graduate degree. I have a job I really like. Fun, right? Yes! It’s great … but … I would like to get a steady man in on the action, and I can’t seem to find a bro who wants a bite of my cool life sandwich.

I am one of the few “professionals” in my friend group. No judging, it just is what it is — I made choices that made me happy, everyone else is making choices that make them happy, fine. But most of the dudes who I like and bring home are in bands or waiting tables or bartending or something, and I think that my job/house/”together” lifestyle freaks them out. This scenario plays out over and over.

Most recently, I went on some really fun dates with a guy I met online who is a really cute dirtbag covered in questionable tattoos who is a great drummer, a fantastic lay, and sweet, and smart. The first time he had me over to his house, he was kind of drunk and got self-conscious about his dwelling — a typical bro-fort: piles of books and records, dark, crazy paint-job on the walls, etc. — and I brushed it off, told him I didn’t care, and we made out and listened to records, and went to breakfast the next morning. Awesome. Two dates later, I showed up to his house to see a movie (looking maybe a little too foxy for the occasion, but I like looking good on a date!), and the same thing happened again when we got to his house. This time, he’s been super-distant. It’s happening again. I will like a man, he will seem to get weirded out by my life, get down on his own life, and then he’ll drift off. I swear, I’m not a troll. I don’t think I’m too clingy. A post-coital text asking for my earrings isn’t crazy, is it?! And then a follow-up three days later?!

It doesn’t help that I’m currently teaching the play A Streetcar Named Desire, and that I’m Blanche’s age, evidently “eligible,” in love with men and whiskey, and looking for something that lasts more than a few hot, sweaty nights. What the fuck, dude? Do I have to start dating other teachers?! They are so earnest and boring! Do I have to go back to grad school?! Am I too happy with my own set-up? I’m about to put on a pretty outfit and pretend I’m at a party from my own debutante days, and forget the fact that I’m spending another drunk night alone in my tiny, affordable (but cute) house! Please, some advice and reassurance! PLEASE! I can’t continue to feel like I can only rely on the kindness of strangers for sex and affection.

There’s no such thing as being too happy with your own set-up or looking a little too foxy on a date. You have a career, and a house and irresponsible friends. You shouldn’t feel the need to sacrifice any of that, especially when your barometer is an insecure dirtbag. You’ve described your recent partners, and they all sound like the same questionably tattooed manchild. Nothing wrong with having a type, in and of itself, some people eat the same thing for breakfast every day for their entire lives, and it always tastes delicious.

My question is, why are you spending so much time in bro-forts if it doesn’t make you feel good? It doesn’t even make the bro of said fort feel good to be in the bro-fort and he built the stupid thing out of his childhood fantasies. Are you trying to become the millennial Blanche DuBois? Is this some kind of Method teaching? Blanche was a fictional, drunken loon and a metaphor for an entire region and generation. You’re a real person. What you need is a change of scenery. As trite as that sounds, it’s the truth. Even when you dipped into the vast pool of the internet, you picked up a drummer. Come on, lady. Didn’t he have pics of his raggedy-ass studio apartment on his profile? Next time, go against type. No more forts, only castles. Pick the guy who’s really into something you’re into (like Broadway dramas) or who appears to have a nicely designed home (I swear I’m not being funny) or writes a bio as descriptive and funny as your question. Maybe a playwright or something. Or advertising copywriter. I don’t know. Find some dude who may not be your cup of warm Jameson on first impression but shares some of your hopes and dreams.

In real life, do you have male friends? Guys you just enjoy spending time with. What are they like? Why do you hang out with them? I’m not suggesting you appraise these guys as potential sexual partners, though you could, but take some time to figure out what basic qualities you appreciate in men you know well, men you’ve spent many sober hours with. Then take that list of qualities along on your next quest for romance.

There are plenty of guys out there who are professional and grounded and interesting, but, if you really want to get off the hamster wheel, you’re going to have to make more of an effort to find them, and don’t be too presumptuous. Some teachers may be boring, but just as many are wild lunatics, in a positive and enriching sense, of course. And, I’m going to go out on a limb here and say that, unless you’re going out with Lars Ulrich (and you shouldn’t be), some drummers/bartenders/waiters are going through a period of personal transition, which is just as boring as grading papers. Some of them are careerist and awesome. Stop picking the low-hanging fruit.

In all honesty, I know that most of us want to meet someone special that we can share our lives with, but I wonder if we (you) also take for granted that this person will just stumble into a bar by chance and interrupt our conversation with the bartender. They will, most likely, not. And since we’re not like our grandparents, who seemed happy to marry the first nice person they met, nor are we like our parents who may have felt obligated to marry the first nice person they met, we’re all going to have to approach this dating business with a little more diligence and rigor than a Google search. You seem to take your professional and home life seriously, so why not your love life? Don’t be a metaphor for this generation.

As an avid reader of the “Ask a Dude” column, I appreciate the candor with which the dudes address the most sensitive of subjects — providing tough love while still respecting the sexual liberation of the contemporary woman. I have always considered myself a woman of the 21st century — uninhibited by the Judge Judy-types who scoff at pre-marital sex, let alone double-digit numbers. I’ve had loving sex in the confines of a relationship, casual sex with good friends, one night stands, and pretty much everything in between. With the exception of a few small penises and a whiskey dick or two, I’ve had a good … err … ride? However, I recently realized that more than a few of my escapades have been the result of alcohol, and the 10s I met at 2 a.m. were more like 2s when I saw them in the sober light of day at 10 a.m. Thanks to my supportive (and also religious) gal pal, I am now the proud owner of what we have lovingly dubbed the Slut Jar — a bedazzled plastic vessel in which I place money if I engage in a nefarious inebriated sex act. A drunken one night stand is $5, whereas a hickey (come on, we aren’t 12) constitutes a $10 fine. However, when I’m “good” I get to take money out — $5 for a sober date, $1 for a drunken evening free of romping. This has worked like magic — in four weeks I have had zero drunken humpfests and one booze-induced DTR with the guy I’ve been quietly crushing on for months.

All rainbows and butterflies and puppies, right? Wrong. Despite my efforts to be a bit more reserved when it comes to P-in-V play, my crush was put off by my previous escapades. He confessed to months of infatuation, but said (in not so many words) that my previous attitude toward biblical relations made him nervous about any long-term potential. What is a reformed slut to do?! (Feminists — burn me at the stake for using the word; but 30 partners does a slut make… I’ll own it!) I live in a relatively small community and pretty much every guy I know either knows about my past dalliances or could easily find out. I’m not ashamed of anything I’ve done, but I don’t want my past to define me. How does a gal who wants to shed the skank rep move her name from the “DTF” to the “take home to mom” list?

If all was right, there’d be a country & western singer named Tammy with a hit named “A Whiskey Dick or Two,” but here we are, in a world where a woman calls herself a slut for sleeping with a number of partners that she’s not ashamed of and then apologizes for it to feminists. I don’t think I even understand where that puts us. Somewhere not good, I believe.

As a resident of one of the largest cities in the world, my inclination is to tell you to just move here and get on with your life. Megalopolises are very forgiving. But that wouldn’t really help. Regarding your basic question, of how to de-skank yourself, I’m actually more concerned about the drinking. The one thing you feel good about is staying sober and not hooking up. Everything else is a mess. Even the DTR (Define The Relationship, for the olds) was a cocktail party. What’s going on with you, lady? What happened that sparked this recent trend of alcoholic regret? If you need the equivalent of a swear jar to stay on the straight line, maybe you should consider speaking with someone trained in addictive behaviors about this. I mean, I’m glad the jar has worked, to some degree, but its effectiveness is going to have diminishing returns, especially when “being good” ultimately means there’s no money in the jar with which to reward yourself. You’re actually rewarding yourself for doing the thing you’re trying to stop doing. In my day, the money in a swear jar went to building a new church steeple or outhouse. You sinned, and you were punished. You never got the money back. Never. The “slut jar” is a zero-sum act of contrition. Man, what has happened to small town America?

The thing is, if you’re unhappy about a pattern of behavior (regrettable sex), you have to determine the source of that behavior and address it (the drinking?). Otherwise, you’re asking the wrong questions (you might be). Have you ever had regrettable sober sex? I mean on the same level as your drunken encounters. If you have, then I’ve misjudged, but it seems you’re saying you haven’t. If that’s the case, then you should stop playing games about your usage of alcohol to deal with certain things in your life. You don’t want to end up standing in your kitchen at 10 a.m. ten years from now, alone, staring at an empty jar, an empty bottle and a passed-out 2.

I am in a new relationship (one month) with a dude that I could possibly see myself with long term (or at least it is a consideration at this very early stage). He is fun, we have a lot in common and he is an overall “good guy” — the kind that would probably NEVER cheat on anyone. So, yay for me!

He has never been married, but I was married for about three years. I was young, my husband (now ex) was my first real relationship and I basically didn’t know what I was doing when I said yes. I mean — married at 24!! Why is that even legal!? We divorced because I grew up, learned more about myself and realized that I was with the wrong person. Along the way, I cheated with someone I met through work. I harbor tons of guilt over this. I never ever thought I would do something like that. It still haunts me. A lot. But it has also made me way less judgmental of others — I can see how and why people make mistakes. It has also made me realistic (not jaded) about adult relationships. Like the song “The Sadder but Wiser Girl,” I am no longer the “bright-eyed, blushing, breathless baby-doll baby.” And I think he likes that about me. I am real.

The issue is that I feel like I need to tell the new guy at some point down the line the whole truth about my past. He should know that I cheated on my husband. That I did an awful thing. But that I learned from it and it has shaped me into the person I am today, the person he is dating. I do not want to be defined by this act, but I do want the air to be totally clear.

My question to you is do you agree that I need to disclose this information? It could end things between us, which would really suck. But then that would make him a judgmental type, which is not really my thing anyway. Or, what if he says he is OK with my past but then every time I’m even talking to another guy, he gets jealous/possessive? I couldn’t handle that either.

If your answer is yes that I need to tell him, then how do you think I should do it?

Last question (jeez, I am so needy) — when do I tell him? I would rather not get too attached if this is going to be a deal breaker, so part of me wants to make this confession sooner than later. But, I also don’t want to jump the gun and say too much too soon. The more he gets to know me, the more he’ll realize this is not my typical modus operandi when in a relationship.

Any sound advice is welcome.

You’ve both been in previous relationships. You’ve both made mistakes in your lives. You’ve both been in love with other people. You’ve both had sex with other people. Ta-da, you’re human.

No one on planet earth is perfect (except Edith and Jane and the rest of the contributors here at The Hairpin™), so don’t be so hard on yourself. You were in a bad situation and made an immature decision. But you were literally immature. This is exactly why no one should marry their first serious boyfriend/girlfriend unless they live on some weird island and can’t get off it. There is so much to learn before you make that kind of commitment.

But to answer your question, there is no need to tell this guy about what happened. Now or ever, really. What would be the point? To unburden your conscience? If that’s what you need, talk to a friend or confidant or therapist. Right now you’re projecting your feelings onto him and predicting nothing but negative results. You didn’t kill anyone, and you’re not a bad person. Deal with your own feelings about it on your own, and let this brand new relationship develop separately. At some point, it will be obvious if it’s something you want or need to share with him or some other guy.

I’m all about keeping it simple so here it goes … nudie photos, what are your general thoughts?

They’re good.

Previously: Man Secrets and “What About That Other Thing I Was Doing?”

A Dude is one of several rotating dudes who know everything. Do you have any questions for A Dude?

Photo by Jeff Banke, via Shutterstock