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Stifler’s mom syndrome

Masturbate to your fist’s content but when it comes to real life MILFs and DILFs, keep your Tang and crackers inside your pants, says Dan.



Q I'm 16 and I like my friend's mom who is 35. She's married and has two kids. But I really like her. What should I do? --Help One Really Needy Youth

A Here's what you shouldn't do: You shouldn't say anything---not to your friend, not to your friend's mother---and you certainly shouldn't try anything.

Here's what you should do: You should masturbate about your friend's mom just as much as you like---and you should take the advice I gave another horny 16-year-old boy a couple of months back (this one happened to be gay, but the advice still applies):

"Worry less about getting your 16-year-old self laid and more about getting your 20-year-old self laid. Get out of the house and do shit, get books and read shit, volunteer for a political organization and change shit. You'll have more boys to choose from in a few years and be a more interesting, informed and attractive guy thanks to all that doing, reading and volunteering. Beat off in the interim, of course, but remember to vary your masturbatory routine (left hand, right hand; firm grip, soft touch; with toys, without; lots of lube, just a drop; et cetera), and try to cultivate your own erotic imagination. (Translation: Don't jerk off to internet porn exclusively; use your imagination once in awhile.)"

Lots of straight boys your age have crushes on their friends' mothers, and lots of men had the same kind of crush at your age. It's a great fantasy, one that fuels entire porn genres. But the potential benefits---a few orgasms for you and maybe one for your friend's mom (if you're any good at this sex stuff, and, at 16, you most certainly are not)---aren't worth the potential costs. A destroyed friendship, a broken family and, depending on age-of-consent laws where you live, a long prison term for your friend's mom---those are high prices to pay for a few lousy orgasms. And that's assuming your friend's mom is even interested, which she almost certainly is not.

Q I have a boyfriend of two years. At the beginning of our relationship, I caught him cheating on me. Not physically cheating, but he was talking to girls and they would send him pics. We worked everything out and now we trust each other. But a few weeks ago, I caught him watching porn. He doesn't know. It doesn't bother me that much, but I was wondering if it could lead to him cheating on me again? --Sent From The Savage Love App For iPhone

A All men watch porn. Some lie and claim they don't, some are so stealthy they never get caught, but all men watch porn. If watching porn led to cheating, then all men would cheat. But not all men cheat. So we can safely say that porn viewing doesn't cause men to cheat. Because all men watch porn. But not all men cheat. (OK, OK: A handful of men don't watch porn. But their numbers are so small that we don't need to factor them into our equation.)

Q My girlfriend and I are loyal listeners/readers. Our kinks fit together beautifully, she's accepting of being monogamish, and we have an amazing time in bed and out. The only catch is her best friend and roommate, who she used to date.

Before they moved in together, the best friend demanded that every Sunday night be reserved for the two of them to hang out. Okay, fine, everyone deserves a night without their SO. But after they moved in together and saw each other every day, the practice continued. The ex complains when I spend the night with my girlfriend at her new digs. After the move, I was taking my girlfriend out on a date when she got a text from the ex asking where she was and why she wasn't home yet. My girlfriend got so upset, we had to call off the date and I took her home to the roommate.

I'm trying to be patient with what looks like controlling behaviour, but it's incredibly frustrating to think I could lose this amazing girl if/when her ex decides to issue an ultimatum. I'm head over heels for this girl, and I don't want to come between her and her best friend. But it's really hard to bite back observations about her roommate's hypocrisy (her lovers practically move in). I don't want to turn into a resentful jerk who makes my girlfriend stressed and unhappy, but the conflicts with her roommate (that I tend to bring on) are already causing her stress.

Am I just being overly sensitive to the roommate's behaviour and should I chill the fuck out, or is it a red flag that this otherwise perfectly awesome relationship isn't likely to have legs? --Frustrated Lady

A Your girlfriend is gonna have to decide who's more important to her: her current girlfriend or her ex-girlfriend. And she's gonna have to decide which feelings are more important to her: her current girlfriend's feelings or her ex-girlfriend's feelings. But those might not be decisions she has to make right now.

You don't say how long you two have been together, and that's an important detail. You can't expect to come first if you've been dating this girl for only a few weeks or months. It's generally a bad sign---a sign of emotional immaturity---when a person puts a brand-new girlfriend/boyfriend first; it's an even worse sign when a new/newish girlfriend/boyfriend demands to be put first. Dating is about discovery: You spend time with a person to determine if they're the one you want to put first "for the rest of your life." (In theory.) During this trial period---the time that falls between a first meeting and a joint decision to make a more serious commitment---your girlfriend's close friends, family members and even her manipulative ex may have a stronger and more legitimate claim on her time and attention than you do.

So if it's been less than 12 weeks, FL, then I would say your girlfriend's willingness to prioritize her creepily controlling ex could be excused. But if you've been dating for longer than three months, if you two are very serious about each other, and your girlfriend still abandons you whenever her ex snaps her fingers...well, that's a very bad sign. Your girlfriend may have a serious and seriously dysfunctional emotional entanglement with an ex. If that's the case, I see confrontations, ultimatums, tears, broken leases and other dramas coming your way over the next three to six months. Decide if she is worth the grief.

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