What Online Dating Taught Me About Sales Outreach

I went looking for love in online spaces.* Instead, I inadvertently found a sales philosophy.

In 2020, freshly out of my second marriage (and with VERY limited dating experience) I started online dating.

Tinder. Match. eharmony. Plenty of Fish.

There were a few others, I forget. I was, as the song has it (see below) “looking for love.”

What I didn’t expect was that it would eventually fix my head around sales outreach. That connection didn’t hit me until over a year ago — and it’s only really starting to click now. But it’s clicking. And it’s sticking.

I’m an introvert. Shy, especially around women I’m attracted to. I can talk to a stump when I’m in the right mood, but walking up to someone and starting something? Not my natural habitat.

Online is. I feel comfortable there. Online dating apps are, I think, a genuine gift to shy guys like me — a place where the opening move is built into the structure and I could just be myself in writing, which is where I often express myself best anyway.

And it’s worked. I’ve had good relationships come out of it. The most recent one lasted a year and felt like — well. It felt like possibly the one for the rest of my life.

She ended it.

So. You figure out pretty quickly that it’s a numbers game, and you only need one yes, and sometimes you get the yes and it still ends, and then you’re back at it.

Which, as it turns out, is also a pretty accurate description of selling.

Selling IS Personal

Making a pitch as a company of one is intensely personal in a way that selling for a bigger brand isn’t. When I reach out to a potential client, I’m not just presenting a service. I’m presenting myself. My judgment. My track record. My taste.

Which means rejection can sting beyond the professional surface.

Do enough outreach and the spiral is easily started. You second-guess your approach, your offer, your copy writing, your entire reason for existing as a human on this planet. (OK, maybe not that last part. But the self-doubt is real.)

I’ve never much cared what people think of me. There’s a small list — maybe a dozen people, if that — whose opinions actually matter to me. But I’d still let the mechanics of outreach — the silence, the non-responses, the ignored follow-ups — get into my head anyway.

Here’s what I’ve carried over from online dating pitches to online sales pitches:

The no’s don’t matter — you were never going to meet them anyway. The person who doesn’t respond to your outreach was not going to become a client. The silence is information, not a verdict. Move on.

Cast a wider net than feels comfortable. Some of my more interesting dates came from “I’m not sure, but maybe” swipes. You don’t know what a good fit looks like until you actually talk to someone. Don’t per-reject people on their behalf. Say an enthusiastic “yes” to at least a conversation.

Online interest doesn’t always equal in-person chemistry. Some conversations that start great go nowhere. A promising discovery call can fizzle. That’s not failure — it’s fit. Move on without drama.

There’s no perfect. There is perfect for you. You’re not looking for a universally acclaimed client. You’re looking for someone whose problem you can actually solve and who values what you do. Smaller target. More useful.

Rudeness is a gift. I was once called an “Amazon-chaser” on a dating app because I’m 5’6” and had the nerve to message a tall woman. My reaction, in order: LOL, then — whew, dodged that bitch bullet.

Someone who leads with cruelty tells you exactly who they’d be to work with. Take the information and move on.

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And then there’s honesty, which I’ve come to think is the most important filter of all.

I met someone for breakfast once who had a significantly different relationship with her profile photos than with reality. I wasn’t expecting perfection — real people have bellies and jiggle and I’ve got my own situation going on — but the gap between the photos and the actual person was, well, large.

We had a nice conversation (and Captain Crunch waffles!). That was it.

Here’s the thing: if someone is willing to misrepresent themselves in a situation where you’re going to find out the truth the moment you show up — that’s not just vanity. It’s a tell. Someone who fudges the easy stuff will fudge the harder stuff.

Same goes for clients. Early dishonesty — about budget, about timeline, about who actually makes decisions — is a preview of the engagement. Pay attention to it.

Honesty is gold. In dating and in business.

A newsletter does the same thing a good dating profile does — it lets people decide if they like how you think before either of you commits to a conversation. If you've been avoiding outreach because pitching cold makes your skin crawl, a newsletter is the warm version. That's what Newsletter-in-a-Box builds. Reply or email me at bryant@simplyusefulmarketing.co if you want to know what the lightest version looks like for your business.

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None of this makes outreach fun. It’s still a grind. It doesn’t make the silence after a pitch feel great, or the end of something that mattered feel like anything other than what it is.

But “a grind I can do” beats “a thing I dread and avoid.”

Most people who don’t respond aren’t rejecting you. They’re busy, or distracted, or the timing is off. It’s not personal.

It rarely is.

What do you do? You get back up on that horse and keep on riding until you get where you want to go.

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P.S. — If you're the kind of person who read this whole thing and thought "yeah, but I still don't know what I'd write about" — that's the first thing we figure out together. It's usually easier than you think. bryant@simplyusefulmarketing.co

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Musical Coda

The sub-heading is a nod to one of my favorite love songs, Looking for Love. Enjoy! I always forget that it’s in Urban Cowboy, also a great movie.