Dating, Relationships, & Sex, Lists, Theory & Essay

10 Things I’d Tell My Teenage Son About Women, Dating, Relationships, And Sex

"Son, I just wanted to show you first hand that there are, in fact, other fish in the sea. Hopefully my ridiculous jeans don't distract you from that point.."

The last couple days of VSB — writing a “fatherly advice” piece for my teenager daughter, and following it up with something for a son the next day — was a plan I’ve had in mind for a while. I thought they’d be pretty well-received and relatively easy to write, and it’s a topic everyone — parent or not — could relate to in some way.

Anyway, with this in mind, I sat down yesterday afternoon ready to write the post about the son, expecting it to be as “easy” as the daughter piece was, but something unexpected happened: It dawned on me that there were actually two completely different sets of dating and relationship tips I could give him:

A) 10 Things I’d Tell My Teenage Son About Women, Dating, Relationships, And Sex If I Want Him To Be Thought Of As A “Nice” Guy, and…

B) 10 Things I’d Tell My Teenage Son About Women, Dating, Relationships, And Sex…If I Want Him To Actually Be Happy

Now, I don’t mean to suggest that you can’t be a nice guy and completely happy at the same time. It’s possible and shit. And, for the sake of the entire community, it’s probably the best way to go. I imagine that cities like Portland and Charlotte are full of happy nice guys, and, if I had a G-IV, I’d definitely fly there whenever I wanted to hit an organic farmer’s market

But, giving my son the same type of “look out for your own self-interests first” type of advice I gave my daughter yesterday — which is what I’m about to do — creates a guy that, while he can still very well be a “good” guy, fathers would probably advise their daughters to avoid. “Woman dating with her best interests in mind” seems to = “empowered” while “man dating with his best interests in mind” seems to = “asshole.

Oh well.

1. Do not even entertain the thought of being married or having children until you’re (at least) 34 years old. 

Now, I realize this doesn’t seem like ground-breaking advice. You’ve probably heard the same thing from your mother. But, what makes what I’m saying different is that while your mom wants you to wait until you’re fully mature and ready to be a husband and father and blah, blah, blah, I’m advising you to wait for one reason: Options.

Why 34? If you take advantage of the great genes your mother and I passed on to you and live the life you’re supposed to, by the time you reach that age, you’ll be successful enough to have some sort of social and/or financial status. And, if you take care of your body, you’ll still be youthful enough to really enjoy it. If you accomplish these things, you will have a better and more attractive range of romantic options than you will at any other point in your life. Asking you to wait until then to choose a life partner is me just wanting you to make the most informed choice possible. You don’t want to be the guy who puts all his chips in too early and then gets all unsettled and unhappy when realizing he could have gotten a better deal if he just waited.

I know you like sneakers, so think of it this way. Why shop at Foot Locker when you can drive a few more miles and hit the Nike Outlet instead?

2. The best, and most consistent way to get women to want to sleep and/or be with you? Act like you don’t really care about whether you’re able to sleep and/or be with them.

This may be the most difficult thing on the list to grasp. Even grown men aware of this truth have trouble pulling it off, as doing this is the equivalent of taking a starving man to the Cheesecake Factory and asking him to act like he’s not hungry.

But, as history has proven time and time again, your success with women is usually directly correlated to how unfazed you are by them. Also, the more beautiful the woman, the more you should probably act as if you barely even notice her beauty.

3. During high school or college, there’s a chance you might be attracted to a woman who attempts to coerce you into doing “boyfriend” duties (hanging out, being a confidant, eating salads with her and shit, etc) without any actual boyfriend pluses (sex). Do not fall for this trick.

You may be tempted to think that just hanging around and being the friend will assist you in finally getting some. It will not. The longer you stay around and continue to volunteer to take her panties to the laundromat, the less likely she’ll consider you to be a romantic option.

If you’re not careful, it may even get to the point to where she’ll complain to you about her man problems — in graphic detail, no less — despite the fact that she knows you’ve been pining away like a…pining-ass motherf*cker. If this happens, dead all contact with her, and  also make sure to steal all of her remote controls.

4. First dates should always be fun. And cheap.

This is your opportunity to set the tempo for the entire relationship. It’s also your chance to vet and see if she’s the type of asshole who needs a $90 steak in front of her to have “fun.”

5. There are thousands of reasons why you should always practice safe sex, and I’m sure you’ve heard each of them before. Here’s one I’m pretty sure you haven’t: Playing the pull out game always makes you feel like an idiot.

I’m not going to lie to you. Unprotected sex does feel indescribably better than wearing a condom. No sense in bullshitting you about that. But, the jump in feeling pales in comparison to the prolonged awkwardness you’ll feel when going raw, pulling out at the last moment, wondering if you pulled out in time, wondering how the hell you managed to cum on her knee, pausing this intimate moment to perform post-coital clean up, wondering if you pulled out in time (again), getting back in bed after the clean up and finding out the hard way that you didn’t do a very thorough clean up job, and feeling bad because you’ll start asking yourself if you’re too damn old to playing the gotdamn pull-out game.

6. Only sleep with women who have something to lose.

Hoodrats and hoochies can (definitely) be sexy, but 5 to 25 minutes of pleasure isn’t worth the considerable potential downside if things go down hill. Basically, never, ever, ever, ever, ever, ever have casual sex with a woman who’d consider it the best day of her life (and the lives of everyone in her family, including her son) if you happened to get her pregnant.

7. The grass is never greener.

Although all women have their own personal quirks and idiosyncrasies to go along with some physical differences, there isn’t much variance about what makes them them. Seriously, if you took 100 random men from Jakarta and 100 random guys from Jacksonville and asked them to list the 10 things that most annoy them about their wives, the lists would look exactly the same.

I’m bringing this up because there may be a point in one of your relationships where you experience a bit of malaise and start fantasizing about how things would be with someone else. When this happens, remember that a relationship with whoever you’re fantasizing about will eventually reach the malaise stage too.

This leaves you with two options

A) End relationships as soon as they leave the honeymoon stage (not the best option)

B) Make sure you commit to the right person so that your love for and attraction to her will help you deal with the inevitable “meh” period (the best option)

8. Smell good.

I didn’t pay much attention in the anatomy and physiology course I took my freshman year in high school, and the way women respond to a guy who smells good definitely makes me think that I must have fallen asleep on the day they explained that a woman’s nose is directly connected to her vagina.

9. It may not seem this way when it happens, but breaking up with a woman can be one of the kindest things you can do as an adult

Look, while we can dick around until we’re in our 40’s and still end up finding a wife and building a family, (generally speaking) women just don’t have that same luxury. If you’re in a situation where you know things probably aren’t going any further and she’s at an age where she’s expecting them to, end it. Shit, even if it’s a good relationship, end it.

You’ll both feel like shit for a while, but you both will eventually get over it and realize it was in both of your best interests.

10. From now until the day you die, your penis will be fighting a never-ending battle with your brain to see who will lord over your body, your decision making, your choices, and your future. You cannot let your penis win, but you also cannot let anyone shame you into feeling bad for being a man. 

This will not be an easy task. Your penis is tricky, dastardly, diabolical, deceiving, deceptive, and indefatigable. Basically, you know how Dick Cheney kind of looks like a penis? Well, imagine that your dick is Dick.

Thing is — and this is very important to note — I’m not asking you to suppress or ignore your sexual urges. They are not bad. In fact, they are very good. Just don’t be the guy who allows those urges to completely dominate everything he does.

That’s enough for me today. Did I forget anything? Also, people of, what advice would you give to your teenage sons?

—Damon Young (aka “The Champ”)

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Damon Young

Damon Young is the editor-in-chief of VSB. He is also a columnist for and EBONY Magazine. And a founding editor for 1839. And he's working on a book of essays to be published by Ecco (HarperCollins). Damon is busy. He lives in Pittsburgh, and he really likes pancakes. Reach him at Or don't. Whatever.

  • Desmond

    Hahahaha. I’m still laughing at #3. I thought I was the only one who absconded with remote controls in spite.

  • #6 just screams AZZ HOLE! What kind of advice is this?!

    Teenage advice to a son————-> I am not going to have a son! I just want a daughter that is it. If it happens that I have a son,I am auctioning him on e-bay!

  • Andre

    …wish I had a pops around to school me on #3. Took me all through HS and two years of college to learn that lesson.

  • dd

    ”Woman dating with her best interests in mind” seems to = “empowered” while “man dating with his best interests in mind” seems to = “asshole” because women have more to lose

  • Eric McD

    I had to copy and paste this to my email so that when my son’s come of age I will be able to refer to this list as “The basics of being a happy man.”

  • “Your penis is tricky, dastardly, diabolical, deceiving, deceptive, and indefatigable.”

    Indefatigable??? LIES!!!! lol

    And Why are you taking her remote controls?

    Anywho, I digress. I suppose this is an okay list. As I have no sons, teenage or otherwise, I she perhaps someday modify and share portions of this list with my nephews.

  • DG

    Good a$$ list, folk…I agree w/ just about everything you said.
    Moreover, you’re right about #1….age 34 is a bit of a sweet spot as far as dating goes right now…at least for guys: lots of beautiful options to choose from, (hopefully) enough resources to make it interesting; enough confidence to know what you’re doing; and, if so inclined, enough experience to be able to recognize a special one when you meet her.

    *I may have to print this list out for my own (future) lil’ knucklehead.

  • That Ugly Kid

    11. Be yourself. Seriously. If you’re the nerd in high school, be the nerd. Don’t compromise your identity for a female. It’s better for you to date a woman who likes you for you, and not the illusion of a man she thinks you are.

    12. Arrogance is okay. Just don’t over do it. Women like confident men, men who can take charge, exude power. Beautiful women love powerful men. I mean, have you seen how sexually attractive your mom is? Well, actually, no you shouldn’t of your mom in that manner. And if you do, we need to have a totally different convo, joe. This be Chicago, not Arkansas.

    13. Being that you are my son, you’ve probably inherited my naturally Zeus/Jupiter/God/Allah/Spiderman-like stamina. This is a gift and a curse. A gift because women love that sh*t. A curse because, well, women love that sh*t. While you’ll most likely want nothing to do with her after Rounds 1 & 2, she’ll want more. And while you won’t be fatigued, you’ll definitely be annoyed that you can’t watch my vintage Dragon Ball Z DVDs.

  • nillalatte

    “2. The best, and most consistent way to get women to want to sleep and/or be with you? Act like you don’t really care about whether you’re able to sleep and/or be with them.”

    Funny, this works on men as well. Funny thing is this might work for some women, but I find this behavior a complete turn off. Ain’t nobody up in this mug trying to get an Oscar. Be real.

  • Royale W. Cheese

    “as doing this is the equivalent of taking a starving man to the Cheesecake Factory and asking him to act like he’s not hungry.”


    I agree with waiting until the mid-thirties to get married. Heck, I’d argue 40.

    1. Just have fun trying to court women and don’t get depressed after being shot down. Why? See the teenage girls rules list. Accept it. Respect it.

    2. I am not your girlfriend’s friend. No she cannot sleep over. No I am not her second mother.

    3. Do not just let a woman declare that you are together. If you are not sure about moving from “kinda sorta” into a full on relationship, dump her.

    4. Learn how to just say hello to women like you are a normal person.

    5. If a girl giggles in response to you, that is not the equivalent of one of your boys pointing his finger in your face and BOLing at you. Do not misinterpret the giggle.

    6. That 5 minute long surround-sound full-color fantasy you have about girl X every 10 minutes is not real. Let it play out, then forget about it.

    7. The strippers hate you. They are here to rob you.

    8. Do not feel jealous about the relative ease at which girls can get chex. Tht “ability” is not all it’s cracked up to be. Let it go and you’ll prevent decades of resentment against girls and women.

    9. Get an education and build your empire and all that because you love to learn and you are passionate about changing the world, not so that you can get more poon. When you let poon drive your actions, you will be perpetually frustrated.

    10. Never rely on a woman to supply the birth control. Just because the baby is hers to gestate doesn’t mean you get off Scott free.

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