Miss Information: Breaking up in five easy steps.

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Have a question? Email Letters may be edited for length, content and clarity.

Dear Miss Information,

I’m thirty-one and just started a new relationship with an awesome guy. He’s smart, funny, creative and caring. But we have a serious problem: he can’t maintain an erection. I go down on him, but I can’t suck hard enough. It’s as if his cock is completely desensitized. When he’s finally able to get hard, just changing positions can make him lose it. I have to rely on masturbating to get myself off. We’ve discussed it, and it may be due to his smoking and drinking habits. He’s seeing a doctor this week.

Also, I’m a bit kinkier than he is, having explored my sub/bottom side. He’s too shy to throw me around, spank my ass, and get mean and dirty and fuck me senseless. All this is frustrating-as-hell, because otherwise things are going great. We get along amazingly well. I just have a lot more sexual experience than him — before me, it’d been three years since he’d slept with a woman. I don’t know if I should cut him loose now, or if these problems can be solved. — Frustrated

Dear Frustrated,

Ask yourself two questions: first, how badly do you want a boyfriend, in particular, this boyfriend? Second, how willing are you to train him?

If you’ve never been the kind of girl who cares about being coupled, or if you just got out of a long-term relationship, then I can see you not wanting to bother. It’s completely fair to want good sex right out of the gate. The ass-slapping and rough stuff is more niche. If you’re expecting a guy who can provide that kind of treatment on the first few fucks, then a kink site might be more expedient than the traditional bar pickup. But straight-up sex — the kind where all the hydraulics work correctly — is not an unreasonable request. Hell, why I am telling you? You know it’s out there. Yet you’re with this guy. The one whose dick doesn’t work.

But perhaps you’re holding off on the boffing because you’re pursuing something higher? It’s not hard to find a dick that fits snugly into a vagina (or other orifices). It’s much more difficult to find a personality that fits divinely with yours. My guy is such an awesome match for me that I watch those BBC documentaries where the woman stays with the husband even though he’s cut off his bits and is wearing women’s clothes — and, as freakish as it sounds, I kind of understand.

If that’s the case — and again, no judgment if it’s not — then the fact that he’s going to see a doctor is a big win. I get letters from people whose significant others won’t seek outside help no matter what, even if it means the end of their marriage. This guy is willing to go talk to a total stranger about his wang troubles for a woman he just started seeing. I know it’s hard to see through your sexual-frustration-tinted glasses, but that right there is quality, my friend.

See what the doctor says. And know that bad sex can get better. But, like any other relationship issue, it requires patience, communication, and knowing what you’re willing (or not willing) to tolerate. What happens next depends on how much you dig him, and how you handle the problem as a couple. Again, listen to how you feel. Lose any self-judgment. You’re not shallow to care about sex.

Finally, consider if you’re oversharing. Openness is great, but can also be unnerving. I’m sure you’re referencing your past experiences in a positive way — but referencing the past still emphasizes a difference. It could psych your dude out. A kid in Little League doesn’t want to be reminded he’s playing against Derek Jeter; he’d rather focus on the game. When you talk to your man, talk about what’s happening here and now, and avoid past comparisons. It’s the best route for future home runs.

Dear Miss Information,

I need to break up with my girlfriend of a year and a half, but I just don’t know how. I guess I have some guilt or shame issues, but the main reason I’m still with her is that I feel sorry for her. I don’t want to hurt her. I like being around her, but she’s too emotional. Her neediness turns me off and wears me out. I know, I know — I should have done it yesterday. But how? — Already Checked Out

Dear Already Checked Out,

If we strip away all the couple-bonding — the dinner dates, the thirteen- and fourteen-month anniversaries, the nights spent spooning in front of the TV — we’re left with a contract. Most contracts require both parties to be acting in good faith, i.e. “a mental and moral state of honesty and conviction.” By staying in a relationship you don’t want to be in, you’re violating that good faith.

Would you do this in other areas of your life? Would you go for months without paying your rent, knowing your landlord needed the money to feed his kids or pay off his bookie? Would you put off finishing a big project at work, knowing the only other career opportunities in your area are HoneyBaked Ham-glazer and car-wash attendant?

You need to move out of that safe, little avoidance nook you’ve created. Realize that your inaction has consequences. You’re stopping her from moving on, you’re stopping yourself from moving on, and you’re upping the burden on your friends and family, as they’re the ones who’ll have to deal with the emotional fallout. That fallout will only get worse the longer you delay.

So, Step 1 is out of the way. Now let’s move on to the rest.

Step 2: Create some emotional and physical distance.
Spend a couple nights by yourself. Talk to your best friend, or put pen to paper and write a “Why I’m Doing This” manifesto. If your girlfriend asks what’s up, tell her you’re feeling really run-down and need some time alone. It’s more or less accurate, anyway.

Step 3: Set up a time to meet. Deliver the unhappy message.
For a relationship this long, the home turf is a good bet. Either one of your residences will work, but hers might be preferable. That way you can leave when you need to, and you won’t have to act like mall security and evict her at some point. Tell her that you want to break up, give her a quick rundown of why, but be careful not to be too specific. If you get too detail-oriented, she might try a point-by-point rebuttal. Generalized statements like “I’m not happy” are much more difficult to argue against.

Step 4: Observe. Absorb. Listen.
Being broken up with is no fun. Some people cry. Some people scream. Some sit silently, or insult you, or ask insanely difficult questions. Your job is to sit there and take it like a bitch. In more refined terms, be respectful and empathetic. Note that this doesn’t mean stoic. You can cry. (Actually, it’s better if you cry. It’s supposed to be sad. It’s not some yippee-skippee pancake breakfast.) But no matter how many tears are shed, you must maintain your position. You must be strong enough to say “no,” even if your heart caves and says “yes.” You must hug when you want to kiss. You must open the front door, not the bedroom door.

Step 5: Set yourself up for success.
I used to work at Bennigan’s, and my manager said this all the time. It made me want to vomit on his Looney Tunes tie and slit his throat with a mozzarella stick. But the message is solid: engage only in activities that will move you out of this relationship. Do not trust yourself not to go back on your word. Do not trust yourself not to make concessions. Going out for drinks late at night at “your spot”? No. Talking over email or meeting for lunch a few weeks later? Yes. If you find yourself saying “I swear it’s not going to be like that,” then you know it probably is.