Back in the Game: A Modern Guide to Dating Again (Without the Weirdness)

Written By Bo Turner

A no-pressure playbook for 24-35 year olds re-entering the dating world, one step at a time.

So you're thinking about dating again... but maybe it feels weird, awkward, or like too much effort. You're not alone. Whether it's been a few months or a few years, this guide is your gentle re-entry plan—real advice, no fluff, no pressure.

This isn’t about "finding the one" overnight. It’s about finding your pace, your people, and (most importantly) your confidence.

1. FIGURE OUT WHAT YOU’RE REALLY LOOKING FOR

Before diving in, get clear on your intentions. Are you:

  • Just curious?

  • Open to meeting new people?

  • Looking for a long-term partner?

Quick Journal Prompt:

"What do I hope dating brings into my life right now?"

Your answer can change—and that’s okay.

2. RESET YOUR MINDSET

Forget what dating "used to be." It's okay to feel nervous or even skeptical. What matters is showing up as your current self.

Reframe It:

  • You’re not "behind" or "starting over."

  • You’re building forward.

  • You don’t need to be perfect—just present.

Reminder: Everyone feels a little awkward. That’s normal.

3. UPDATE YOUR PROFILE (AND PERSPECTIVE)

If you're using apps, keep it simple. You don’t have to be the most clever, just genuine.

Tips for bios:

  • Start with: "These days, I'm into..."

  • Avoid long lists; use one or two specifics

  • Use recent photos (yes, that means from the last year)

Good Opener Examples:

  • "What's a small joy in your week?"

  • "First round: coffee or cocktails?"

4. HOW TO MEET PEOPLE IRL (YES, STILL POSSIBLE)

Apps aren't the only way. Try this instead:

  • Attend small group events (like FIND socials or workshops)

  • Trivia nights, group workouts, or creative classes

  • Ask friends to invite you out to mixed group settings

Pro Tip: Don’t treat every outing like a date. Think of it as re-learning social muscle memory.

5. COMMON MISTAKES TO AVOID

We all do this when we’re rusty. Here are some things to watch for:

  • Overplanning: Just meet up, don’t build a fantasy.

  • Overtexting: Save the getting-to-know-you for in person.

  • Dating out of boredom: Pause if you're not in a healthy space.

Mantra: "I date because I want connection, not because I feel incomplete."

6. PRACTICE DATING WITHOUT PRESSURE

It’s okay to just try. You don’t need chemistry right away. You’re learning.

Try:

  • Low-stakes coffee walks

  • Event-based meetups (less pressure to "perform")

  • Practice flirting in non-romantic situations (servers, cashiers, etc.)

7. BONUS: THE "BACK IN IT" CHECKLIST

Use this quick checklist to see if you’re ready to dip your toes back in:

✅ I can name at least one thing I’m excited about outside of dating

✅ I know what I’m looking for (even if it's casual)

✅ I have at least one recent photo I feel good about

✅ I can laugh at awkward moments

✅ I’m curious about people, not just outcomes

If you checked 3 or more: You’re more ready than you think!

WHAT'S NEXT?

You don’t have to jump in all at once. Start with small steps. When you're ready, check out FIND events near you—low-key, social, and designed to help people connect naturally.

Bo Turner
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