With the fantasy season over, the mailbag will take a necessary turn towards the sex and relationships, as there are only so many questions that can be asked about which guys are keepers and who in the NFL draft could have a fantasy impact. Ugh, the NFL offseason is terrible.
However, longtime readers of the mailbag know that there are also a finite number of sex questions, many of which have been answered repeatedly over the years. In lieu of a mailbag this week, I’ve created a FAQ that I’ll bookmark and use for definitive responses moving forward. If some of these answers seem like common sense, congratulations: you are well-adjusted enough to not need the free advice of a blogger.
SHOULD I DATE MY CO-WORKER?
BUT SHE’S REALLY HOT!
Will that vagina pay your bills? No? Then your job is more important.
MY GIRLFRIEND IS GREAT BUT I’M NOT SURE IF SHE’S THE ONE BECAUSE OTHER WOMEN ARE ALSO ATTRACTIVE AND I LIKE THE IDEA OF SLEEPING WITH MORE PEOPLE BEFORE I GET MARRIED. WHAT SHOULD I DO?
This all depends on your age and how happy you are in your relationship, but that whole “I want to have sex with more women” thing never really goes away. It’s programmed into your DNA, and getting married doesn’t shut off your biology. But, speaking as a married man, I reached a point in my life where building a home with my then-girlfriend and spending my life with her and starting a family sounded great, and going through the motions of dating — the small talk, the loud bars, condensing my life story into something that got told over dinner — was only slightly less appealing than eating glass. My wife is the right person for me, but — equally important — I met her at the right time.
Do people still play Texas Hold ‘Em? Because I’ve got a poker metaphor for you. Think of marriage as going all-in. You obviously only want to go all-in with a winning hand — but what’s a winning hand? Even pocket aces can lose, and I’ve had entire nights where I never saw a pocket pair. So you wait for a good enough hand to play, collect information, and go all-in when you’ve got the best chance to win. Ten-eight suited can turn into a straight flush; sometimes nothin’ can be a real cool hand.
There’s skill involved, of course, but luck and timing are equally important, otherwise your douchebag friend wouldn’t be married to that Brazilian girl.
Anyway, the metaphor falls apart when you realize that the cards have a say in whether you play them, but this much is true: committing to someone for the rest of your life is a potentially costly gamble. Be smart about it.
HOW DO I CONVINCE MY GIRLFRIEND TO TRY ANAL?
First of all, try to understand that not all people want foreign objects in their butts. Of course, some people REALLY like foreign objects in their butts, but you can’t expect everyone to feel that way. Some girls don’t want you to ejaculate on their face, either. Porn isn’t reflective of real sex, so don’t expect every girl you date to emulate Asa Akira, not that I know who that is.
BUT: if your girlfriend is interested in trying it, start small. One finger, then two, then, I don’t know, there are things called “starter butt plugs.” You can find them online or at your local sex shop. Lubrication also helps — both the literal kind and booze beforehand.
MY GIRLFRIEND PUT SOMETHING IN MY BUTT AND I LIKED IT. AM I GAY?
Only if you are attracted to men.
MY GIRLFRIEND AND I ARE GOING TO LIVE IN DIFFERENT PLACES. SHOULD WE DO LONG-DISTANCE?
FUCK YOU, WE’RE DOING IT ANYWAY. ANY TIPS?
Sigh. Okay, yes:
- Long-distance relationships work best when there’s a set end-date. “We’re going to different grad schools for three years, and then we don’t know where jobs will take us” is unlikely to succeed. “She has to finish a contract on the West Coast, but she’s moving back in six months” is a smarter course.
- Enjoy your Skype sex. Someone once wrote in saying that his girlfriend was worried about being hacked/recorded during a Skype session. If that’s a concern, your LDR is not built for success.
- Avoid sexy co-workers.
- If you have anything less than complete trust in each other, don’t bother.
- Visit as frequently as possible (duh). Enroll in an airline rewards program, or, if you’re close enough to drive, get yourself some good books on tape.
MY BEST FRIEND’S GIRLFRIEND/FIANCEE IS AWFUL AND WE ALL HATE HER. HOW DO I TELL HIM TO DITCH HER?
You don’t. For all the talk of “bros before hos,” men will always side with the person giving them orgasms. I dated someone pretty awful my senior year of college, and one of my friends pulled me aside and was like, “Hey man, she’s bad news, and she’s not even that hot.” He was absolutely correct, and I repaid his kindness by distancing myself from him and continuing to date the girl. Pussy control is a real thing, which is why Prince is America’s most revered poet-statesman.
This is a fight that you can only lose. Take heart that not all relationships last forever, but know that the same is true for friendships. Be supportive of your friend, and save the shit-talking for after they break up.
MY SIGNIFICANT BROKE UP WITH ME. I’M DEVASTATED. WHAT DO I DO?
Go ahead and feel sorry for yourself for a little while. Take two to four weeks to drink more than you should and listen to every sad song that you own. Break out photos of her for masturbation sessions that end in tears instead of orgasm. Be a miserable bore to your friends, who want to support you and hang out with you, but not if you’re just going to mope all night.
There. You got to wallow in your misery. Now it’s time to move on with your life. Let’s go to some numbered steps.
1. Realize that you shouldn’t want to be with someone who doesn’t love you.
“But what about all the hot sex and funny banter we had?” you ask. SHE STOPPED ENJOYING IT. SHE DOES NOT WANT YOU. It’s stupid and selfish to want to be with someone who doesn’t want you.
2. Break off all contact.
Don’t do that “let’s be friends” bullshit. Your ex-girlfriend wants to be your friend for two reasons: (1) so she can continue to receive attention from you, and (2) so she doesn’t have to feel so bad about rejecting you. Fuck that noise, let her feel bad. If she’s keeping you on the emotional hook by remaining in contact with you, ask her to stop because you want to focus on moving on with your life. From then on out, no contact. I SAID NO CONTACT. Block her on Gchat. Hide her Facebook timeline from your feed. No email, no texting, no anything. Pretend she’s dead. So sad she died, right? Oh well, better get a move on with your life.
3. Begin self-improvement.
Don’t worry about dating or rebound sex. (If you’re comfortable with it, go right ahead, but understand that re-entering the dating world can be a depressing experience after the emotional/sexual cocoon of a relationship.) Take your sadness and anger and your newfound free time and funnel it towards self-improvement. Start a new workout regimen. Sign up for cooking or bartending or wine-tasting classes. Throw yourself into your job. Volunteer for a children’s program or animal shelter. Out of the pyre of your failed relationship will emerge a stronger, more knowledgeable, and more caring person with new circles of friends from your new activities. YOU ARE A MAGNIFICENT PHOENIX.
In time, the more fit and more interesting person you become will also be naturally more confident, and you’ll end up dating women who are better looking and smarter than the stupid bitch who broke up with you in the first place.
Not only is living well the best revenge, it’s also living well, which, y’now, is kinda the whole point of life. And almost as nice as REVENGE!
So that’s it for the FAQ. Now go out there and have responsible sex and communicate with your significant others! WOOOOO!!!!