How NYC Dating Culture Saved My Business in 2025

Recently, there was a moment in my business journey when I feared we’d have to close our doors. Our typical sales methods yielded 0 results after years of success. We had no clue where to turn next. Ironically, what pulled me out of that slump wasn’t a more complex or expensive marketing strategy—it was a messaging campaign inspired by what I learned dating in New York in my 30s.

Here’s how I booked several new clients and ended up saving my business: 

1. I was nice to everybody.

Whether it’s someone I’m chatting with at an event or someone I DM on Instagram, kindness goes a long way. You never know who might open a door for you—or who’s watching silently from the sidelines, rooting for you. When you’re nice to everyone, it makes it easy when you want to reach out to the person that’s going to move the needle because you’re well practiced. Plus you get to make people’s day better in the process! 

2. I spent time with people I like, doing what I like.

This one’s major. When I genuinely like the people I’m around, being kind and collaborative becomes effortless. The work feels lighter, the conversations flow easier, and the connection feels natural. This is why my calendar is filled with people I’m excited to meet up with. 

3. I used personal (or at least semi-personal) messages.

Email blasts might save time, but a little personalization goes so much further. A “Hey, I thought of you when I was working on this” message makes people feel seen—and more likely to respond. Plus having true human connection makes everyone involved feel good. Rebecca and I sent out over 100 personal messages and I got to chat with people I haven’t connected with in a long time. 

4. I sent out as many messages as possible at once.

This sounds counter intuitive, but hear me out. When you send one message and sit around waiting for a response, your brain starts playing games. You second-guess yourself. You spiral. But when you send 10, 20, or 30 at once, you take the pressure off. You stop obsessing over the outcome and start building momentum.

5. I do it in community.

There’s something powerful about reaching out together. Whether it’s a co-working session, a group challenge, or just texting an accountability buddy that you’re about to hit “send,” sharing the experience keeps me from feeling isolated—and makes it more fun.

6. Ask yourself: how would I feel if someone reached out to me like this?

We often think we’re bothering people. But when someone you admire or genuinely like reaches out to you with a thoughtful message, how do you feel? Probably flattered. Maybe even excited. At worst? Indifferent. And that’s okay. The truth is: people rarely get annoyed by a kind, respectful message. Unless they already don’t like you—which is exactly why you should be reaching out to people you already love and respect.

Bonus: Give yourself permission to be sh*t.

Seriously. Your first message doesn’t have to be perfect. Your reach-out strategy doesn’t have to be flawless. Just do it. Take messy action. It’s better than standing still and it’s what saved my business.

The truth is, business isn’t always a straight line. Sometimes it looks like going back to basics. Sometimes it looks like taking lessons from your dating life and applying them to your professional one. And sometimes? It looks like leaning into your network, showing up as your full (imperfect) self, and asking for help.

That’s not weakness—it’s power.