Jamie Shupak is the Emmy-nominated traffic reporter for NY1, the Big Apple cable network that’s the end-all and be-all on all things Gotham for New Yorkers. She’s also a beautiful, single woman navigating New York’s treacherous dating scene after the painful breakup of a 10-year relationship. In her weekly column she’ll share her war stories and offer her advice and admonitions.

About a month ago I was catching up with a friend on G Chat and I asked her about her ex-boyfriend, whom she’d hung out with that weekend:

Even though this particular case involved an ex, the same goes for when you’re actually in a relationship.

We want to learn from you, but we don’t want you to teach us. We want your opinions, but we don’t want you to advise us.

Don’t be the coach; play on our team.  

We have teachers, bosses, and dads for constructive criticism, guidance, and lectures on how best to do things.

By being Mister Critical, you are just being Mister Critical Error.

But what if you truly don’t like something the woman you’re dating is doing? Or you really think that she could put more effort into something, or make a change she often talks about?

It’s easy. You wait for her to bring it up first, then with compassion — compassion — you tell her how you feel in the most proactive way possible.

If the topic is her weight, do not engage. I repeat: Do not engage. You tell her she looks beautiful the way she is, and change the subject.

If, however, she’s trying to decide on what to wear and she asks your opinion, give it to her, but again, in a positive way. So you hate the green dress she has on, fine, but don’t say that. Instead, you tell her that the green one is nice, but she looks really hot in that other black one she wore to that party a few weeks ago.

While I would never encourage lying or suppressing your opinions, this is one instance where I’ll give you a free pass because it’s in the name of being delicate with, and sensitive to, your woman’s emotions.

When it comes to work, make it a group effort. If she hates her job or is dying for a raise and you’d really just love to tell her that maybe if she got to the office on time, wasn’t on Facebook all day, or stayed past 6 o’clock, she might have a shot, don't. Instead, suggest that the two of you make a list together of all the reasons why she deserves the promotion, or help her figure out what she can do to get where she wants to be in her career.

By lecturing in a situation where she already feels helpless, as my friend’s ex-boyfriend did to her, you are making it worse, not better.

Being critical is condescending and not nice. It sucks the life and confidence right out of our stride and also — not to be taken for granted — pushes us away physically. No woman wants to make out with a man who criticizes her.

Trust me on this: Flirting, playing, and being sensitive draws us in. Being Mister Critical has the opposite effect.

You become the social assassin, a la Larry David, but of your own relationship. While Curb Your Enthusiasm is hilarious, look at how well it turns out for him with the ladies.

There are always going to be things that bother you about the woman you’re with — things that drive you nuts and things you wish you could change. Try your best to turn the volume down on those traits or behaviors and instead focus on the good in her, the reasons why you liked her in the first place.

By doing so I think you’ll feel luckier than you thought — in more ways than one.


So, what did you think of the column? It was smart? It was well-written? Aw, gee, thanks.

See…? Not that hard.

Next Week: Jamie’s theory on dating inertia.