An urgent dispatch to my 12-year-old self about dating and masculinity

Dear younger self: Popular culture will provide you with a distorted sense of masculinity. Exhibit No. 1: Grease.
Dear younger self: Popular culture will provide you with a distorted sense of masculinity. Exhibit No. 1: Grease. Observer file photo

Dear 12-year-old Matt,

You’re gonna want to sit down for this. It’s me … that is, you. I’m 44 years old now, writing you from the year 2018, and there are important things you need to know.

Some men here in the future are facing a day of reckoning. Others, a day of awakening. Women are bravely calling out seemingly countless men who have sexually assaulted, harassed or manipulated them. The good news is, #TimesUp for such atrocious behavior (more on “hashtags” in coming letters). That said, I think it’s important that you have a #HeadsUp on something.

Matt Olin

There’s a major malfunction of expectations and communications occurring between dating adults, as evidenced by a recent exposé of happenings on a date between a young woman and a popular comedic actor, Aziz Ansari. I’ll spare you the gory details, but many assert Ansari was intentionally manipulative, while others feel he’s just super-awkward in sexually charged situations (or some combination of the two). So at risk of altering the course of history, as I look back on our dating career, I feel I must intervene with some retrospective insights for you. I just hope this letter reaches you in time.

First off, in modern dating, things can progress at an unpredictable pace, making clear communication vital. Unfortunately, long-engrained male/female messaging causes cues to be misdelivered and misread with alarming frequency.

Let’s see if we can head some of this off at the pass, my boy.

As you grow up, be prepared for an onslaught of societal suggestions of what “real masculinity” looks like. You’ll contend with a slew of masculine standards set by Men’s Health covers, Hollister models at the mall and varied popular culture artifacts. Be especially wary of Grease, Grease 2, Bill Clinton, Maxim magazine headlines (e.g., “Lower Her Inhibitions”), Roadhouse, and that episode of Saved By The Bell when Slater ultimately wins Jessie’s heart. Beware, too, a forthcoming brand of entertainment called “reality TV” teeming with abysmal male role models (including a show called The Apprentice … I have some really bad news about that host, but we’ll hit that next time).

You’ll also be subjected to a variety of entrenched notions about relationships. You’ll be fed a steady diet of absurdities like “men always make the first move,” “good girls prefer bad boys,” and the classic carte-blanche permission slip, “boys will be boys.” You’ll be introduced to the supposed benefits of cat/mouse dynamics, the insinuations of hard-to-get, and the asserted sins of being “whipped.” These notions can maliciously infiltrate your developing mind and create a perverse disconnect between male/female expectations. Don’t take the bait.

Good news/bad news: Pretty soon, you’re also going to find yourself enjoying easy and immediate access to pornography via something called the World Wide Web. Your instinct will be to see this content as a requisite source of information about sex and sexuality. Be warned, however, that it will simultaneously introduce contaminants, bugs and bad information to your system.

Matt, as you get older, you’ll realize that you’re not 100 percent certain of the meaning of the phrase “good sex” and – unless unforeseen developments occur – you’ll likely end up having relatively limited experience in actual human-on-human sexual interaction. As a result, you’ll incur a sexual knowledge gap in critical areas such as: general understanding; confidence; language; adeptness; suaveness; what women want; prophylactics.

Listen up, buddy. Sex is supposed to be exhilarating, not scary. So get out there, ask girls out, make mistakes and have fun – but remember to always be respectful.

And look, Matt, you’re also going to have a few “killer ideas” regarding women that you think are really solid. Let me clear one of these up for you here and now. Don’t stand at the end of a girl’s driveway in a trench coat holding a boom box. Might seem like a good idea. Two words: Restraining Order.

Good luck,


P.S. – Spoiler Alert – we’ve somehow married an amazing woman and created a beautiful daughter. Learning how to listen and understand is really important. Start practicing. And don’t screw it up.

Actress Alyssa Milano got an idea from a friend of a friend on Facebook to elevate the Harvey Weinstein conversation. She took the idea to Twitter, posting: "If you've been sexually harassed or assaulted write 'me too' as a reply to this tweet." T

Email: mattolincreative@gmail.com