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I’ve always considered myself a great “wing woman.”

Last week I pitched my single friend of sixteen years to a room full of single women for a live show called Pitch And Pair. It went smashingly.

And by smashingly I mean it was lovingly hilarious, and he should be smashing plenty…

I am still handling DMs from these women on his behalf — literally sending him screenshots of their numbers and telling him which ones to give a shot at a date to.

I love being a connector. In my twenties my favorite nights out were when I was winging for a friend, especially a guy friend. Lord knows men struggle with being smooth.

I remember when the movie Hitch came out I was like, “It me!” — minus the insane level of income Will Smith’s character in that movie seemingly derived off his efforts.

But that’s just the dating wing woman version… 

The week before that show, I connected that same friend to potential investors for his real estate expansion (he owns bars and restaurants throughout Chicagoland).

Not because I'm in real estate or finance, but because I just “got a guy.” I always know someone who can solve a mutually beneficial need for someone else, I have a big network, and fuck it — people trust me.

That's the business wing woman version.

(Also, wouldn’t it be cool to get your friend both a multi-million dollar deal AND a wife??)

And then there's the family version, where I'm somehow the connective tissue holding everyone together. I'm the one my grandmas call when they need to coordinate with my mom. I'm the one my mom calls when she needs to understand what my grandmas need. I'm the one everyone calls when someone else in the family is acting weird and they need intel.

I’m the one who always listened to dad’s feelings in a chaotic house full of women.

I've always been the glue. The one who reads the room, senses what people need, and figures out how to make connections that shouldn't logically work but somehow do.

Whether it's setting up my friend with potential dates, potential business partners, or potential solutions to problems they didn't even know they had — I see the patterns. I trust my gut about people. I wing it based on what feels right, not what looks perfect on paper.

Being everyone's wing woman can be exhausting, but it has actually made me really good at winging it in general.

The same instincts that help me read a room full of strangers? Those same instincts help me navigate comedy clubs and bookers, business meetings, and family dynamics.

Turns out, the art of winging it isn't about being unprepared. It's about trusting your ability to read situations and adapt in real time.

It’s a skill I’m damn proud to have.

The Hustle

I've learned that the wing woman advantage is actually a superpower in disguise.

While everyone else is networking with business cards and LinkedIn strategies, I can walk into a room and find the right person to talk to based on vibes.

I can walk into any event and within fifteen minutes know who should be talking to who, who's looking for what, and who's full of shit.

And I don’t care if anyone is someone “worth knowing” if I can smell shit on ‘em.

The same instincts that tell me my friend should definitely swipe right on the woman once divorced but avoid the one with self gratifying charity photos? Those instincts tell me which business partnerships will work and which will implode. Which comedy bookers actually give a shit about great comics and which ones just like to feel important as a gate keeper. Which investors are serious and which ones are just collecting pitch decks for their ego.

Being a wing woman teaches you to think three moves ahead.

You're not just making introductions — you're reading personalities, anticipating compatibility, and setting people up for success. You learn to spot red flags faster than an arena bull. You develop an almost psychic ability to sense when someone's about to make a terrible decision. (Myself included).

In business, this translates to everything. I can walk into a room of strangers and know who the real decision-makers are within minutes. But that doesn’t mean I gravitate towards them. If their energy is off, I don’t care if they’d hand me a million dollar check.

Dirty money from dirty people makes dirty deals.

I trust my gut about people because my gut has a pretty impressive track record. When I connect my restaurant-owning friend to investors, it's not random. I can sense that their personalities will mesh, that their business styles align, that they'll actually like each other as people beyond the deal, even if the deal doesn’t pan out.

That's the wing woman advantage.

Friendly Reminder!

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The Chill

The flip side of being everyone's wing woman is sometimes you forget you need wings too.

I assume whoever was behind the marketing for Redbull felt this big time.

When you’re the connector, the glue, the person everyone calls when they need something figured out — it can be exhausting. Not the good kind of exhausting where you feel accomplished. The kind where you realize you've spent so much energy reading everyone else's room that you've forgotten what you need in your own.

I love being the family translator. I love knowing exactly which friend to call for which crisis. I love that my gut instincts about people are basically a superpower. But somewhere along the way, I became the default solution to everyone else's problems.

Family drama? Call Natasha, she'll mediate. Friend needs a business connection? Natasha knows a guy. Someone needs dating advice? Natasha will wing woman the hell out of this situation. Need to fill up tour dates? Natasha will refer you to bookers.

Don't get me wrong — I love helping people and I'm good at it. I genuinely enjoy helping people connect and succeed. But being everyone's wing woman can sometimes mean you're flying solo more than you'd like.

The art of reading the room includes reading your own energy levels. Knowing when you've given enough. Recognizing when someone is asking for your help because they trust your judgment versus when they're asking because they don't want to do the work themselves.

Not every introduction you could make is one you should make. Not every problem you could solve is one you need to solve. Not every room you could read is one where you need to be the designated interpreter.

Sometimes the most generous thing you can do is let people figure things out themselves. Sometimes the best wing woman move is knowing when to fold your wings and focus on a nice stroll for a little bit.

I mean, if you're always everyone else's wing woman, who's yours? 🦅

Upcoming Shows

Saturday May 2 — Laugh Factory Chicago, 7pm

Thursday May 7 — Headlining Comedy at the Cabaret in Madison WI

Friday May 8 — Laugh Factory Chicago, 7pm

**If you ever want to come to shows at Laugh Factory, reply or message me for comp code! I have endless comps for that club for the rest of my life until I die and I’ve earned them and love to give them to you.

Love you all and cheers to the hustle + chill. We appreciate our wings.

xx NPH