How To Look For Love Like An Entrepreneur

Lacey Artemis
7 min readMar 14, 2022


Approaching love like a business? So unromantic! Hear me out.

I’m a diehard romantic. It’s true.

Over the years i’ve shifted the way I approach many things — not just love! But as someone in several niche groups that tend to have smaller dating pools, I’ve had to get more resourceful. And if there’s one thing an entrepreneur knows how to do, it’s be resourceful!

There are (at least) two ways to look at it.

There is the common (and frustrating) advice I’ve often heard. That you will find love when you aren’t looking or when you least expect it. It will just happen. Which to my frustrated mind, reads like ‘so don’t even try to date, it will only work against you!’

The other idea is — If you’re going to looking for something long term and committed (whether it’s monogamy or a polyamorous ‘anchor’ partner), you want to make sure right? You don’t want to waste your time or their money, right? That’s another thing entrepreneurs tend to know a lot about.

An entrepreneur would look at this similarly to say, buying a car. Cars are expensive and you want them to last you a long time. You want a lot of ‘bang for your buck’ (no, that’s not meant as a double-entendre). So you do research, and you test drive a few cars — ideally from different makers. You gather data, and you make a decision. What car has the features you desire? What feels like the best fit?

Here is the way I’ve come to look at it. The different car companies in the analogy are are not just like the different dating apps. They are also different approaches to dating.

There’s apps, blind dates, meeting at a friend’s birthday part, speed dating events, matchmaking services… And of course ‘the old fashioned way’ — meeting at a bar (though as someone who doesn’t drink, this was never an option for me).

For the longest time I relied just on the apps, but I wasn’t getting a lot of results. At one point I decided to ‘lease the fancy car’ and I signed up with a matchmaking service.

In retrospect, when I was an active client I was still too underdeveloped of a person and had more growing to do, so the service was less effective for me. There’s another lesson — know your product, and in dating your product is yourself!

Entrepreneurs have to learn to market their product or service, and by extension, themselves! No one will want to buy from you if you seem sketchy. But also if you don’t know what your true offering is, you’re not going to be able to sell as much of it either.

Since ‘leasing the fancy car’ didn’t ultimately pan out for me when I tried it, I had to go back to doing the leg work for myself (and working on myself). And of course, you have to be persistent if you want to grow and to find what you’re looking for.

Better In Real Life

I discovered more recently that I do much better in person. This definitely didn’t used to be the case.

I discovered this just before the pandemic happened. When in person, in real time, it’s much more often that someone I’ve just met enjoys talking to me and wants to do it again. Text-only communication limits my appeal, even for people who might think I’m outwardly attractive.

I used to be very socially awkward and shy. It was easier for me to write a 10,000 word email than to have a 10 minute conversation. I reached a point where I was not satisfied with this and began pushing myself to get better at talking. To be more dynamic.

This was also part of my process of becoming an entrepreneur. In a sense, I wanted people to pay me to be myself, to do the things I enjoyed and was good at. Of course in my early days I still wasn’t 100% clear on what I was offering, so it was a clumsy process.

Me from ten years ago would be stunned at where she ended up today. Now when I think back to doing my first real public speaking gig 8 years ago, it feels quaint.

When it comes to dating in a pandemic, a lot more of the process has been forced (back) online. More initial communication has to go through an app, or through texting (if you both agree to switch to that quickly). So text, text, text you go. A lot gets lost in text-only but I do my best.

I can think of several times in the year or two prior to the pandemic where I felt effortless and glowing at an in-person hang. I felt like I could read the room a lot better and adjust my metaphorical ‘pitch’. Over text that can be harder to tell.

Some people are more comfortable meeting quickly, while others aren’t. Both are valid.

Since I am more comfortable meeting quickly, it appeals when the other person is too. It shows greater interest and greater comfort, which means they’re on a similar wavelength. In business, you want your customers to be like you. In dating, you also need the other person to share a certain amount in common. Values, beliefs, future plans.

Since I got better and more comfortable at talking to new people and strangers, I tend to do well meeting new people in person or on facilitated zoom calls. The tone and vibe is a lot more discernable. It feels more natural to me, and I can play off the energy and mood. I can get a better sense of who is on my wavelength.

Whenever I see old videos of myself I tend to see my best self in them. It reminds me of what I have to offer, of what just can’t quite be fully expressed though static text alone. Effective advertising these days often needs to be more dynamic, less static.

So my advice is try to (safely) get back out there as soon as you can, unless you actually prefer the apps.

The Swiping Game

I’ve been waiting patiently for this Omicron wave to pass so I can get back to being my best self out in the world more often. But yes the pandemic has forced me to change my approach. When in person isn’t an option, I’ve had to be resourceful. There’s that word again!

I’ve test driven pretty much all of the apps. OKCupid, Tinder, Bumble, Hinge, HER, Lex, Taimi, Feeld, BiCupid… In test driving these apps I got a better sense for which were better for what demographics, or you could say target markets. That’s another thing entrepreneurs need and like to know about.

Tinder for example is probably the app of choice for straight cisgender people. HER started as an app for lesbians only but eventually opened up to a broader userbase. Lex is specifically meant for queer folks. Hinge and OKCupid are both good all around choices.

Find Your Community

Another route I took that has shown some promise, is connecting to communities. When you connect to a new community that has dozens or hundreds of members, you increase your chances of connecting with one or more of them. So if you can find a community centered around something you’re really passionate about, that is a great place to start!

There are communities for lots of things. Crafting, music, board and video games, sports, mental health, even for being single! You name it there is probably a community online somewhere. They aren’t all big communities but they all still increase your chances.

Funny enough the matchmaking service I used before led me to a community of entrepreneur women. One of the members led me to a community around sexuality. That led me to another community around queerness and relationships.

In non-pandemic times and times of year when indoor events are safer, I go to what events I can that are relevant for me. This is also a good way to network and connect in an organic, less-schmoozey way.

Because once again I’m trying to make the most of things, like an entrepreneur.

I’m used to being efficient and resourceful in my small business which I spend a lot of time on. So that type of thinking tends to naturally apply to other things as well. It’s the standard way I think about and approach most things.

Even when not in pandemic times, my life still largely revolves around the computer. Between writing, graphic design, video editing, and my day job, it’s a lot. As such, it had been helpful to be able to rely on the apps temporarily. But I’m glad that restrictions are finally lifting and people are starting to feel more comfortable meeting in person again.

Let’s Review Shall We?

Here’s a recap of the concepts that apply to both being an entrepreneur and looking for love.

You want to know your options and do your research so you find a good quality version of what you’re looking for. You don’t want to end up with a lemon!

Your customers and/or would-be lovers will likely be on a very similar wavelength to you, so know what you offer and how to best present it over a variety of mediums.

Find your community! It’s like the least schmoozey way of connecting with the right kind of people.

Make use of the tools at your disposal when you have to improvise in a changing situation (such as going on dating apps more when a pandemic makes in person dates less safe).

Be dynamic, and of course authentic!

What is the most resourceful way you’ve met or connected with someone new for a romantic connection?

Lacey Artemis is an author, artist, musician, podcaster, and more. You can find all of her work online at

Hat Collecting (YouTube, Spotify, Apple Podcasts, Google Podcasts)
My book! My Music! Twitter |Instagram |TikTok | Patreon



Lacey Artemis

Perpetually curious, creatively inclined ambivert. Ponder, write, repeat. she/her.