Should You Try (or Re-Try) Online Dating?

Online Dating
Written By Sandy Tran

🕒 Estimated reading time: 4 minutes

Ever stood outside a party wondering if it’s even worth walking in?

That’s how a lot of people — especially those who are newly single in their 40s, 50s, or 60s — feel when it comes to dating apps. They’ve heard horror stories. They don’t use social media. The idea of flirting through a screen feels awkward at best, disheartening at worst. And yet… dating apps are everywhere. So the question lingers:

Should you try one?

Let’s break it down.

Why Dating Apps Feel So Strange (Especially If You Didn’t Grow Up With Them)

Black-and-white spiral pattern creating a hypnotic visual effect, symbolizing confusion or disorientation.

For many people, online dating feels disorienting — like being pulled into something strange, repetitive, or hard to make sense of.

For many people, especially those re-entering the dating pool after a long time away, the whole experience of online dating feels… off. The way people interact can come across as transactional. Matches vanish mid-conversation. Messaging feels more like marketing than connection.

There’s also a perception that apps are full of bots, scammers, or people who aren’t serious — and that perception isn’t totally unfounded. Reports estimate that Tinder’s user base is roughly 75% male, with a relatively small percentage of those users actually looking for a relationship. Many are swiping casually, out of boredom, or using the app sporadically — all of which can lead to lower match rates and communication drop-offs .

Apps can also feel like they weren’t built for you if you’re over 45. While some platforms like OurTime or SilverSingles exist, reviews often cite clunky design, poor user experience, and steep subscription fees. In general, most dating apps cater heavily to users under 44, with usage dropping significantly among older demographics .

What Most People Don’t Realize About Dating Apps (From a Product Perspective)

Dating apps are built by product teams optimizing for metrics like engagement and revenue — not necessarily your dating success.

Here’s something you won’t see in the app store: dating apps are businesses. And like most consumer tech products, their design choices are influenced by business goals like:

  • DAU (Daily Active Users)

  • Retention and re-engagement

  • Revenue from subscriptions, boosts, and premium tiers

In short: the longer you stay on the app, the more money they make.

Tinder, for example, earned over $1.8 billion in 2023, mostly from paid features like Super Likes, Boosts, and Tinder Gold subscriptions (Statista). Even Hinge — with its feel-good slogan “Designed to be deleted” — is owned by Match Group, a company that also owns Tinder, OkCupid, and Plenty of Fish. While these platforms differ in tone and branding, their core business model is similar: monetized swiping and premium access.

This doesn’t mean they’re evil. It just means their incentive isn’t necessarily to help you find love quickly — it’s to keep you engaged.

So… Should You Bother?

A hallway with seven identical white doors against patterned wallpaper, evoking a sense of choice or uncertainty.

Trying a dating app is like walking into a room full of closed doors — there’s no guarantee what’s behind them, but it might be worth exploring.

Honestly? Maybe.

Here’s the thing: a dating app is just one way to meet people. It’s like going to a party, a conference, a networking event. There’s no guarantee you’ll meet someone — but it’s a room worth walking into if you’re curious.

About 12% of U.S. adults who’ve used dating apps say they’ve found a long-term relationship or marriage from them (Pew, 2023). That’s not nothing. But it also means most people don’t find lasting success through apps alone — especially if they expect it to be easy, instant, or "just like meeting someone in real life."

If you decide to try, treat it like an experiment. Here’s how:

5 Ways to Make Dating Apps Work for You — Without Losing Your Mind

Treat online dating like an experiment — set goals, take notes, and learn what works for you.

  1. Time-box your effort.
    Give yourself 4–6 weeks. Spend no more than 15–30 minutes a day. Set boundaries upfront so it doesn’t become a draining time sink.

  2. Optimize your profile.
    Use clear, recent photos. Write a bio that reflects your personality and what kind of connection you’re looking for.

  3. Learn the etiquette.
    Messaging can feel like a foreign language if you haven’t dated in years. Keep it light, curious, and don’t be afraid to move things along.

  4. Move off the app quickly.
    Suggest a quick video call before a first date — it’s a great way to screen for red flags, confirm chemistry, and save time.

  5. Observe, don’t judge.
    Instead of trying to “win” at online dating, treat it as a place to observe human behavior — including your own. What feels good? What doesn’t? What do you learn?

The Bottom Line

Dating apps are imperfect. The incentives are messy. The experience can be confusing. But if you go in with low expectations, clear boundaries, and a spirit of curiosity, you might find they’re one more place — not the only place — to meet someone interesting.

And if you try it and hate it? That’s data too. You’ll learn what works for you and where to look next.

If dating always seems to follow the same frustrating pattern, it might not be the app — it might be a loop you haven’t spotted yet. Here’s how to break the cycle.

—

Want Help Getting Started or Refreshing Your Profile?

I offer 1:1 coaching and run regular workshops to help people navigate dating — online and offline — with more clarity and confidence. Check out DateLabHQ.com to learn more or join an upcoming event.

📚 Recommended Reads from the Blog

If you're thinking about trying online dating — or want to make it less frustrating — these might help:

Sandy Tran
Next

Breaking the Cycle: When Dating Feels Like Déjà Vu