Investing in dating startups is a lot like dating itself.

Despite the likelihood that most won’t go anywhere, investors still back a lot of these companies. This is because they still believe that, once in a while, something transformative will come from it.

As is typical in the startup world, the biggest, best-known dating platforms and apps started as modest efforts. Tinder’s creators cobbled together their prototype in days over a hackathon. Grindr’s founder paid a software developer $2,000 to build the initial app in 2009.

Looking at more recent funding rounds to startups focused on dating and romance, the general ethos still emphasizes starting small. Among those who do raise capital, rounds are commonly a few hundred thousand to a few million. Anything above $10 million is a rarity.

For a more nuanced sense of the trends, we put together a sample set of 28 dating- and romance-centric companies funded in the past couple years. Out of the full list below, which covers everything from gamified dating to AI companionship, the median last round size was just $1.5 million.

Beyond the swipe

The largest funding rounds have gone to companies looking to make the dating experience more fun and engaging. Offerings seem particularly geared toward a generation of singles weary of the shallowness and tedium of endless swiping.

One example is Smitten, an Icelandic startup that has raised $13 million to date for a Generation Z-focused platform it says “operates at the intersection of dating, gaming, social and entertainment.” The app prompts matched users to engage over yes-and-no questions and a lie-guessing game.

Meanwhile, Cleveland-based Datefit, which raised a $9 million venture round in July, aims to get users away from their screens. The startup matches people looking for friendship or relationships based on fitness activities they enjoy.

And just in time for Valentine’s day, newcomer Blush raised $7 million earlier this month for an invite-only dating app that seeks to connect people at events and favorite local gathering spots.

Love in a time of AI

Of course, no list of funding recipients would be complete these days without at least some touting their artificial intelligence capabilities.

In the case of dating, one taking this route is Couple, a startup offering online singles parties with AI matching. The company also recently launched DateABot.ai, a platform where users can “date” a selection of bot characters it claims are specially designed to be “empathetic, engaging, and incredibly attuned to our needs and responses.”

On the romance front, San Francisco-based Digi is also experimenting with how much humans will enjoy relationships with AI partners. Its initial app allows users to interact with a customized avatar with the hope they’ll become “a companion that truly understands and evolves with you.”

Others working on AI romantic partners didn’t make our recently funded company list. This includes Replika, known for its AI companions. While we’ve yet to see if AI romantic companions catch on at a mass level, early pioneers in the space are largely offering the same basic pitch — that these bots can at least seem more empathetic and compatible than the humans we meet.

Failures and successes

Not all apps make it, even with sizable funding. A recent case in point is Toronto-based Clover, a dating app developer that announced plans to go public through a SPAC merger in late 2022. A few months later, Clover and SPAC sponsor FoxWayne Enterprises Acquisition Corp. disclosed they were breaking up and terminating the agreement. The Clover app is no longer accessible.

Still, longstanding success stories are out there. Grindr, for instance, is a $1.5 billion publicly traded company today.

Another standout is Match Group, parent company of Tinder, Match and other dating apps. True, it has shed roughly three-fourths its share price value since the late 2021 peak. However, Match is still a $10 billion market cap company and profitable, with more than $3 billion in annual revenue.

Among more recent startups, we’ve yet to see who, if anyone, will deliver a big outcome. From the spectators’ seats, I’m rooting for those companies that still aim to help us find actual people for love and companionship. But given trends in AI, it wouldn’t be entirely surprising to see some of the more chatbot-oriented apps also getting more affection from investors.

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Illustration: Li-Anne Dias