Breaking Up With: Cheaters, Travel Partners, and the Decrepit

by A Dude

I’m engaged to a really great guy. I’ve known him for about two years, I love him to pieces, and he does everything in his power to make me feel loved, too. But he has a very sordid history when it comes to commitment. He has dated just three girls seriously before me, and cheated on all of them. He’s up front about it, and none of the cheating ever lead to a relationship with the fling-lady; he would just get some action on the side until the girlfriend found out and they broke up, then go on his merry way without girlfriend or fling-lady. He isn’t proud of it, but he also says that he isn’t ashamed of it: The relationships weren’t great by the time he strayed, and he was immature and once it worked that first time (i.e., got him out from the first girlfriend via cheating), he just kind of fell into that pattern.

I have never cheated on anyone, and (to my knowledge) never been cheated on. I know a lot of people do it, but it seems the ultimate betrayal to me, and I never think it’s justified. My fiance knows my feelings on this, but he says that obviously OUR relationship is different, and he is different, and he loves me like he’s never loved anyone else, etc. And I believe him. But I bet his last girlfriends believed him when he said he loved them, too. I know everyone has their baggage, but logically, doesn’t it seem stupid to expect a leopard to change his spots [insert any similar lame metaphor here]? He claims he always cheated because he was too chicken to just break up, or was testing the waters before breaking up, and it was never about moving on to the greener grass or the like, which is a bit of a comfort (since conceivably he will never want to break up with me, what with the marriage and all). He’s honest and great and I love him, but I’m getting jitters about 10 years down the road busting his ass for cheating, and feeling like an idiot because HELLO WARNING SIGNS from his past. Do you think that “once a cheater, always a cheater” is true?

Hello to YOU! It’s Warning Signs. So glad you got back to me. Was starting to wonder since you didn’t seem to notice me even after I sang the entire Carly Simon catalog in the style of 18th century Cantonese opera and then set the woods behind your house on fire.

Anyway, now that I’ve got your attention, I guess it’s good that this fellow feels close enough to you to have this conversation in the first place. It could be proof that he has indeed matured and realized how ridiculous his prior behavior was. Dudes are capable of that kind of growth sometimes, especially as we move out of puberty.

However, the skeptic in me wants to ask, what if he also had this conversation with his ex-girlfriends? What if this is his way of laying a sort of doubt foundation so that you’re subconsciously prepared when he Draperizes that ass in a few years? To be honest, it rings of gaslighting, but I may have just watched too many Ingrid Bergman movies.

I would actually have a little more faith in him if he was ashamed of his indiscretions, or if he’d stayed with one or two of the women he cheated with. At least that would’ve indicated a desire to be in relationships, even if he was profoundly terrible at the transition between them. Meaningless cheating as an escape route shows significant disregard for the girlfriends he cheated on and the women he cheated with, which is obviously problematic, because he clearly did not hold infidelity to the same moral standard then as you do now.

Which brings us to the more difficult question of whether one’s basic moral character can evolve over the course of one’s life, or, more specifically to your question, over a few years. My feeling is no, probably not. Has yours? His entire life led him to make those poor decisions. Has something happened to reverse that course? Has he been to Tibet recently? Near-death experience? Ate a really hot pepper? We’re not exactly talking about a guy facing extreme ethical dilemmas here. He took the absolute lowest road out of these relationships. So whether he would repeat the exact behavior or not, do you trust him to fight for you when it’s not easy? Because I think we can all agree that a marriage will be a lot less easy than his prior relationships.

It is possible that the legally binding contract of marriage could act as a behavioral firewall for your dude, though when I look at Brad Pitt, the requisite celebrity analog, I still see a man who would sleep with Anne Hathaway tomorrow if he thought Angelina would not cut his penis off and make a puka choker from its bits.

I’ve had two of my recent-past-now-ex boyfriends tell me that A) They wish they met me when I was 16, or B) They wish they had met me when I was “still a virgin.” I’m 27 now, and had a few sexual partners but am by no means the town pony. Why do guys say shit like that? Do they know how insulting that is?

Who said this?!?! Are they 16? Are they virgins? Did you meet them on a website with a very literal domain name regarding a sexual preference for teens and/or virgins? Your question begs more context, but without that opportunity available to us (comments, if you like), I’m just gonna go with, Your exes are ridiculous assholes. And suggest that you continue to make exes of any guys who say things like this, unless you’re in the middle of role-play and you are dressed as Abraham Lincoln. What guy wouldn’t want to meet a 16-year-old Abe Lincoln? What was he like? What were the origins of his facial hair? Did he play soccer or read in the library during lunch period?

For what it’s worth, I learned to ride on the town pony. His name was CJ, he was the color of August stormclouds, and he was very gentle with me.

Hi. I’ve recently been presented with an awesome opportunity to travel abroad (for free) with one of my good guy friends. At first, it started off as us reconnecting after we “lost touch” with each other for about four years, and over the past few months we’ve both realized that we are really compatible and possibly “falling for” each other (cheesy, I know). He’s brought up the idea of getting married so that while we are abroad I can have full medical and dental insurance (just in case, right?) I always thought I would be the ultimate single lady, and eventually cougar for the rest of my life, and surprisingly I am OK with this and the idea of staying married if things work out in Asia.

The only problem is that his occupation (which is providing the opportunity to travel abroad) is extremely stressful, and since he’s been back in the states he’s been struggling with severe depression and anxiety, not to mention he’s a very intense person on top of that. I don’t necessarily have a problem with this since I do care about him a lot, more than I’ve ever cared about anyone, and I want to help him through this rough time in his life, but my mom thinks otherwise and wants us to just remain “friends.” She pointed out various reasons why I shouldn’t get “too serious” with him and that I’m too young to know how I “really feel” (I’m 24 and just graduated college, I feel like I need to make my own decisions at some point), and I will find someone “more compatible” with me when I am older…blah, blah, blah. I mean, I respect my mom’s advice and understand why she feels this way (she married my father young) but the idea of marriage really doesn’t mean much to me, besides I will have all the legal benefits that come with being married and I’ll be hanging out in Asia with someone I really love to be with. Any advice??

Man alive! What is going on around here today? DO NOT marry this guy. That’s my advice. Do I need to elaborate? Okay fine. First of all, the “few months.” Second, the “falling for.” Third, the travel insurance. Fourth, cougar ambitions. Fifth, being surprisingly OK with the idea. Sixth, the depression. Seventh, LISTEN TO YOUR MOTHER. Jesus. Eighth, “I feel like I need to make my own decisions at some point.” Ninth, “the idea of marriage really doesn’t mean much to me…hanging out in Asia.” I know I’m supposed to be the sage here, but get it together, lady! I feel like forwarding this to Michelle Bachmann to illustrate how the sanctity of marriage ain’t so sanct and it’s not the mentally sick gays making it that way, but I won’t. Cuz I know you’re reading, girl! But again, do not do any of what you wrote. Maybe go to Asia.

I’m a little terrified to actually write in a question, because usually the answer to these things is something totally obvious to all of humanity except yourself, because you have starry eyes blah blah blah. It reminds me of that “He’s Just Not That Into You” book that I read during my impressionable youth. But anyway.

There is this guy who I have been talking to for about a year. We talk on the phone for hour(s). We chat online and send each other stupid/awesome YouTube videos. The conversation is genuinely easy — very random and lighthearted. We send witty strings of flirty texts. But this fellow has also advised me on some real things. I probably talk to him as much as anyone else in my life.

Unfortunately, the only time he ever asks me to do something it is usually 1 a.m. in the morning. I’ve gone over a few times, with full knowledge of what a 1 a.m. invite implies. We haven’t slept together, but we have fooled around, and OMG CRAZY INSANE CHEMISTRY. I’m fairly certain it’s mutual.

Why will this man not ask me out on an actual date? Is he just not that into me? Every time I tease him about his booty call habits he’s all “no you’re really special and smart and beautiful and I talk to you more than anyone else!” etc. etc. Which is unnecessary because I’m definitely not giving wounded lady vibes.

Here is the thing — I would just write him off as an obvious player (which maybe he is), except I get the sense that maybe he has a hang up about the fact that I’m younger than him. By a fair amount. I just graduated from college, while he is nearing thirty. I feel like I’ve earned my place at the big kids’ table; I have a professional full-time job and my own apartment. And most guys do not seem to have a lot of hesitation about dating someone younger. Could this be a thing, though? If yes, is there a way to soothe his elderly fears?

I know he keeps going on (unsuccessful) first dates with ladies who perhaps could be deemed more age-appropriate. I also have been dating other people, but I don’t mention it so much to him. When I told him about one particularly good date, he all of a sudden wanted to go out on a real date (but the timing didn’t work for me). I JUST DONT UNDERSTAND. Again, I would write him off, but the level of cameraderie/chemistry is kind of unique. I have a fond spot for this dude.

OK, I look forward to your advice.

My friend, never feel terrified to ask A Dude. This is a safe place. Also, since it’s anonymous, if the obviousness of my answer feels embarrassing, you can post a comment and be like, “How did this woman not know this obvious advice UGGHHGHHH,” and no one will be the wiser.

More importantly, never feel terrified to ask a real life dude. Specifically, this chemically-attractive, early-morning phone-calling, potentially unsavory dude. As in, have you asked him if he has an issue with your age? If you have not, you should. He may not answer truthfully at first, mostly because he’ll worry that an honest answer might lead to an end to all the good stuff you mentioned (read: 1 a.m. jammy jams), but press him gently for a response. Let him know that you don’t mind dating someone so much older and closer to death. Make him feel at ease but also aware that he’s extremely lucky to have the companionship of a youthful and vivacious beauty such as yourself.

If he answers, “Yes, you are too young for me to date in public during normal business hours,” dump him: He doesn’t respect you. If he says, “Yes, I did have a problem with it, but I now realize how silly I was being,” dump him: That’s wishy-washy, and he’s old enough to know better (so old). If he says, “No, I never even thought about it actually,” dump him: He’s lying, or he’s just not that into you. Wait, make out with him one more time if you’re already over at his place, but get a cold first, and then dump him.

Honestly, any guy who really likes you, regardless of age (or any other) difference, will not hesitate to flaunt you to all of his friends and the general public. He’ll want to be seen with you. He may still call you in the middle of the night, but it’ll be because he forces himself to leave your side once a month to keep up appearances with the gang.

Dump Dump Dump. Dumpfest. Dump all these guys! Next week I want to see some more encouraging questions!

Previously: Job Opportunities, Older Professors, and Angel Hair Pasta.

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