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13 Ways Men Can Make Dating Fun Again

Updated on May 19, 2025 by TMM Staff · Dating & Confidence

A man and a woman laughing and lying on a blanket in the grass.
©Leah Newhouse/Pexels.com

Dating isn’t a job interview. Instead of obsessing over impressing someone, focus on enjoying the experience. The less pressure you put on yourself, the more relaxed and fun, and the interaction becomes stronger. A real connection is easier when you’re not trying to “win” every date.

Table of Contents

Toggle
  • Ask Questions Because You’re Curious
  • Pick Playful Date Ideas
  • Stop Trying To Perform
  • Laugh on Purpose
  • Embrace Imperfection
  • Turn the First Move Into a Game
  • Don’t Let Swiping Drain You
  • Bring Dating Back Offline
  • Shake Off Ghosting Gracefully
  • Celebrate the Small Wins
  • Add Social Vibes to the Mix
  • Keep a Healthy Life Outside Dating
  • Challenge Yourself Creatively
  • Remember the Real Goal

Ask Questions Because You’re Curious

A man and a woman talking to each other outdoors with a mountainous landscape in the background.
©Vanessa Garcia/Pexels.com

Drop the checklist mentality and bring genuine curiosity. Ask questions because you want to understand the person, not because you’re measuring them. This shift creates better conversations and more memorable dates. When you’re present and curious, dating becomes a lot more rewarding.

Pick Playful Date Ideas

A man and a woman walking and holding coffee cups in a city.
©Katerina Holmes/Pexels.com


Switch things up from the usual dinner and drinks routine. Go for an outdoor walk, play mini golf, or hit up a night market. Activities ease tension and spark laughter naturally. Dates that feel like experiences, not obligations, tend to lead to better connections.

Stop Trying To Perform

A man and a woman walking arm-in-arm with a city skyline in the background. The woman is holding a rose.
©Budgeron Bach/Pexels.com

You don’t have to act like someone you’re not. Being genuine is more attractive than trying to be perfect. When you stop performing, the pressure fades and real chemistry has a chance to grow. Authenticity always makes dating feel more natural.

Laugh on Purpose

 A man and a woman laughing outdoors, with the woman holding a book and a flower.Image Title: Couple laughing
©RDNE Stock Project/Pexels.com

Don’t underestimate the power of humor. Playful banter and light jokes make dates feel easy and fun. You don’t need to be a comedian, just be open to finding the humor in the moment. Laughter breaks the ice and creates an instant connection.

Embrace Imperfection

A man and a woman eating ice cream and talking.
©SHVETS Production/Pexels.com

Not every date will be magical, and that’s perfectly fine. Even awkward moments can be fun if you don’t take them too seriously. Stop aiming for flawless and start embracing what’s real. Imperfect dates often make the best memories.

Turn the First Move Into a Game

A man and a woman playing frisbee in a field.
©Anastasia Shuraeva/Pexels.com

Approaching someone doesn’t have to feel like a risk. Frame it as a playful challenge: can you spark a genuine moment? Whether online or in person, focus on curiosity over conquest. This mindset shift makes the process more relaxed and fun.

Don’t Let Swiping Drain You

A man hugging a woman from behind, both are smiling and looking at the camera.
©J carter/Pexels.com

Dating apps are useful, but they can also lead to burnout. Limit your time scrolling and prioritize real conversations. It’s better to connect deeply with one match than chat half heartedly with ten. Quality over quantity keeps dating enjoyable.

Bring Dating Back Offline

A man and a woman sitting at a table in a cafe, talking and smiling.
©Jonathan Borba/Pexels.com

Not all connections have to start on an app. Strike up a conversation at a café, bookstore, or fitness class. In person moments are more spontaneous and often more memorable. Dating in the real world adds authenticity and excitement.

Shake Off Ghosting Gracefully

Silhouette of a person standing alone looking out at a body of water with a cloudy sky.
©Lukas Rychvalsky/Pexels.com

Getting ghosted is frustrating, but it doesn’t have to ruin your vibe. Don’t take it personally or spiral into self doubt. See it as redirection, not rejection. The more you bounce back, the more fun you keep in the process.

Celebrate the Small Wins

A man and a woman playing pool.
©Ketut Subiyanto/Pexels.com

Did you have a great conversation or try a new opening line? That’s a win. Not every date needs to lead to a relationship to be worthwhile. Viewing dating as a practice helps you stay positive and makes each step more satisfying.

Add Social Vibes to the Mix

A group of four young people sitting together outside, smiling.
©Анастасия Быкова/Pexels.com

Group meetups or casual double dates can be less intimidating than one on one plans. Shared energy brings comfort and fun to the table. When the environment is relaxed, connection feels easier. It’s dating with a built in support system.

Keep a Healthy Life Outside Dating

A group of people sitting around a campfire at night, some are playing musical instruments.
©Kindel Media/Pexels.com

When dating takes over your calendar, it can start to feel like work. Make sure your social life, hobbies, and downtime stay balanced. You’ll show up with better energy and clearer intentions. Fun comes easier when you’re not burnt out.

Challenge Yourself Creatively

A man and a woman having a picnic in a field, with the woman resting her head on the man's thigh.
©Vlada Karpovich/Pexels.com

Make dating a game for your own personal growth. Try a new date spot, experiment with your style, or initiate a bold opener. These small experiments keep things exciting. The more playful you are with the process, the more fun it becomes.

Remember the Real Goal

 A man and a woman sitting on a ledge near a fountain, looking at a book together.
©RDNE Stock project/Pexels.com

You’re dating to connect, not to perform, compete, or checkboxes. When you focus on enjoyment and presence, better outcomes follow. The most attractive quality in 2025? A man who actually enjoys getting to know people. Make dating fun again, and it’ll start working for you.

Dating & Confidence ethical clothing, sustainability, Tentree

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About TMM Staff

The Modest Man staff writers are experts in men's lifestyle who love teaching guys how to live their best lives.

If an article is published under TMM Staff, that means multiple writers worked on it. For example, sometimes several of us have experience with a certain brand, so we collaborate to publish a more thorough review.

Or, if an article was originally written by one person, but then it was updated by someone else, we'll re-publish it under TMM Staff.

Remember: all of our articles (including those below) are written by real people with decades of combined experience in men's fashion and lifestyle topics.

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