The Inside Man

Tackling modern dating, raising good men and how parents piss us off

Man and woman illustration Man and woman illustration


Tackling modern dating, raising good men and how parents piss us off

Sean Hotchkiss

When I sat down with Valet.’s editor to discuss doing The Inside Man, I was adamant: “I want it to be an advice column,” I said. “I want to answer people's questions.” In truth, though, both of us had doubts if anyone would actually write in. We had the stats that said advice columns for men didn't work. That guys rarely asked for help. That all dudes were islands. All the usual B.S. Which is why I couldn't be more excited that all summer we have been getting real, reader-submitted responses—lots of them! So many, that I got to sift through and pick out some truly fantastic queries that I think can really help a lot of men.

Thank you for proving us wrong, and answering the call. Thank you for your questions. And please, keep writing in (details below). Every other month, we'll pick a few questions to tackle here.



I'm 30, and dating has been a relatively new occurrence for me. However, most of my relationships end the same way. There's a lot of interest and intensity in the first few months, but then I lose interest and begin to crave alone time. Have I just not found someone I want to be with long-term? Am I not interested in a long-term relationship? Maybe there are too many options out there with dating apps?

- Shelby

Hi Shelby,
Oof. This one hits close to home. My initial feeling is this loss of interest goes deeper than the things you listed. Did you experience any heartbreak in your teens or twenties? Any relationships that ended that were particularly difficult? Usually, when we bail out of relationships, or have a lot of casual relationships, we're protecting our heart from being hurt again. We are equating commitment with pain, and so we don't go too deep with another person. Once the unicorns and rainbows are over, we're on to the next partner. This cycle can be rationalized easily by It's just not the right person, or There are just too many options. Many of us are pros at finding reasons not to stay.

I'd encourage you to let yourself really lean into the feelings that come up around month three or four when you want to run. But—and here's the key—don't leave. (At least, not immediately.) When the discomfort and the desire to run arises, work with the underlying feelings with a therapist or coach. Some examples could be: I feel like running right now. I feel like this person is going to leave, trying to smother me, whatever you feel. By going into the feelings you can identify misbeliefs you might be holding onto such as: Every time I commit to someone, it's painful and I get hurt. Then you can work with self-forgiveness to relieve yourself for buying into these beliefs that keep you locked in the loop. This is the kind of work we do in coaching sessions. Oh, and familiarize yourself with attachment styles—from one Avoidant to another, it'll help shed some light on your relationship patterns. Remember, no man is an island. Thanks so much for writing in!


I want to raise good men. How do I instill openness to intimacy and feeling in my pre-teen sons?

- Donnie

Hi Donnie,
Earlier this year, I had the privilege of interviewing a Boys' Psychosocial Development expert at Stanford by the name of Judy Y. Chu. She told me something that stuck with me: “Watch a four-year-old boy walk into a room,” she says. “He isn't concerned what anyone thinks, he's totally exuberant, totally in his feelings. But watch that same boy several years later, once he's entered school. Usually he hangs back, reserved, careful not to reveal too much.”

This is the predicament we find ourselves in thanks to the patriarchal structure of our culture—boys learn to deny parts of their humanity in an effort to be “a man”. The voice that tells your sons to shut down will be loud, but my encouragement is, at home, make your voice of acceptance even louder. Provide a safe space for your boys to express whatever they're feeling, even if it's totally inconvenient for you as a parent. Celebrate their vulnerability. When you don't, own it and make amends. The container is key. When we do work in my Thursday Night Men's group, what we're doing is providing the safe space that our guys never had at home—a place where they're encouraged to bring forward their most vulnerable, open and least “cool” selves. As Peggy Orenstein wrote about in her fantastic book Boys and Sex, the average young man's world is hyper-repressed—he feels he has to be tough at school, tough at home, tough with friends. So your willingness to create a space where your sons can drop their guard is the work at hand.

Of course, providing a safe, compassionate space for your kids requires doing the work of getting to a compassionate place inside yourself. In other words: making your own self-care (this can include: therapy, exercise, a stillness practice like meditation) a priority will have a positive effect on your family. Every man I know who does his own inner work becomes a better father, partner, colleague and community member. When we start to fill up our own loving cup, the good vibes tend to overflow onto those around us. Your email here is a good start!


My parents are posting racially insensitive material on social media. It's not so much their views that scare me, but the fact that their views turn into action online and thus taint the way I'm perceived to others who might see this. Should I just ignore it? Hide their posts and not discuss the news with them? Just deflect any feelings I may have about what's right and wrong? Any other alternative opens the door for more resentment.

- Zhenya

Hi Zhenya,
Very timely with this one. Wish I could have gotten to it sooner. The fact is, a lot of us are seeing the generational divide very clearly these days. My parents have been glued to CNN since March, and there was a time during early quarantine where if my mother said Anthony Fauci's name one more time, I was considering cutting her out altogether. (Mostly kidding.)

The predicament with your parents seems hard. It's understandable that you'd feel angry and frustrated if they're online posting about things you don't believe in, and furthermore, could actually reflect poorly on you by association. But similar to Shelby's question above, I would encourage you to look beyond the situation itself to the feelings you're having. As boys, we learn to use anger to cover up our vulnerability or hurt. It's a more acceptable emotion, because it's tough. So usually, when we get pissed as adults, there's a lot of hurt underneath. My friend Elliot likes to use the Rage Against the Machine line: Anger is a gift when he's talking about the men's work we do, because anger points us in the direction of where our pain is—and when we know where the pain is, we can use that to our advantage.

All of us feel misunderstood by our parents. (It's practically cliché!) But what isn't cliché are the very real feelings we have about it. Feelings that can carry into adulthood and come out anytime our parents do something that doesn't seem to take us or our needs into account. My guess is your parents posting things you deem offensive on social media taps into a younger version of you who felt really pissed with your parents back in the day. And though it's totally counterintuitive, the way to work with this isn't to deflect it, but dive in! Give that little boy some airtime by writing in a journal, talking openly with a trusted friend or facilitator, or my favorite: driving around in your car and screaming at the top of your lungs. (Man it feels good!) Those inward processes you can do for yourself are the key to cooling off the tensions with your parents. Ultimately, you're never going to be able to force them to grow. But you can always grow yourself.


You’ve now got a life coach at your disposal. Hit Sean up with any concern you’re currently struggling with: Trouble at work? Relationship worries, family struggles or general mental health concern? Let him help you tackle it each month in this column.

Drop us a DM, tweet
or email

More of
The Inside Man