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First Date Didn’t Go as Planned? 17 Hacks to Get That Follow-Up Message

Updated on December 12, 2025 by TMM Staff · Dating & Confidence

A couple hugging on a sidewalk in an urban street.
©Natalia Sobolivska/Unsplash.com

So the date didn’t exactly blow Hollywood away. Maybe you got nervous, maybe the food took forever, maybe you both sat there thinking, “Sooo… now what?” It happens more than people admit. What makes the real difference comes afterward. Those little moments can say, “Hey, I’m actually pretty fun once the awkward stage passes.”

Here are clever (and totally normal) ways to turn that meh first encounter into something way better next time.

Table of Contents

Toggle
  • 1. Don’t Try To Force Things
  • 2. Leave Them A Bit Curious About Your Life
  • 3. Ask About Something They Told You To Show You Were Listening
  • 4. Slow Down With The Emojis
  • 5. Show You Liked The Date By Mentioning A Moment From It
  • 6. Text At A Time That Feels Random And Fun
  • 7. Send A Quick Voice Note
  • 8. Add A Little Flirty Energy To Keep Things Exciting
  • 9. Drop Their Name Like You Actually Enjoy Saying It
  • 10. Let The Conversation Breathe If They Go Quiet
  • 11. Suggest A Hangout That Sounds Fun
  • 12. Joke About The Awkward Stuff So It Feels Lighter
  • 13. Point Out Something Cool You Noticed About Them
  • 14. Post Something That Shows You’re Out There Having A Good Time
  • 15. Bring Up The Moment That Made You Both Crack Up
  • 16. Give Them A Little Space Before Popping Back In
  • 17. Shoot Them A Chill Message That Sounds Like You

1. Don’t Try To Force Things

A person holding a smartphone and a white mug while sitting at a desk.
©Getty Images/Unsplash.com

When you reach out afterward, keep it super casual. No pressure-filled paragraphs or essay-length explanations of your intentions. A short “had a good time” shows confidence without the pushiness.

Let the conversation flow instead of shoving it forward. Think of it like tossing a ball lightly instead of hurling it straight at their face. You want them to want to toss it back.

2. Leave Them A Bit Curious About Your Life

A person using a smartphone outdoors at a wooden table.
©Paulina Herpel/Unsplash.com

You don’t need to spill every detail of your childhood, goals, and tax bracket all in one message. Share a playful hint about what you’re up to, like “about to do something legendary in the kitchen. Fingers crossed the smoke detector stays silent.” Now they’re picturing you doing something fun.

Leave a few stories “to be continued,” and it opens the door for future chats (and future dates).

3. Ask About Something They Told You To Show You Were Listening

A person wearing earphones and a gray hoodie using a smartphone outdoors.
©Getty Images/Unsplash.com

Pick up a thread from the date and tug on it: the book they mentioned, the sibling they joked about, the weird hobby that made you laugh. Say something like, “How did that meeting with your boss go?” or “Did you ever finish that show you were bingeing?”

It proves you weren’t drifting off while staring at the dessert menu. Following up on their life makes you feel thoughtful, and people notice when someone remembers the small things.

4. Slow Down With The Emojis

A person sitting on a chair outdoors while looking at their phone.
©Nathan Dumlao/Unsplash.com

Sure, emojis are fun, but overusing them can make your message look like a fruit salad exploded on screen. One or two can bring personality. Forty of them look like you’re trying to win an emoji Olympics.

Let your words do the heavy lifting. It keeps your texts playful without overwhelming their eyeballs.

5. Show You Liked The Date By Mentioning A Moment From It

A person sitting at a desk using a smartphone beside an open laptop.
©Getty Images/Unsplash.com

Instead of the classic “Had fun”, try something like, “I’m still laughing about that menu with two pages of potatoes.” When you call out a shared moment, you bring back something you both lived through, even if it was slightly awkward.

That tiny callback sends a message. You noticed them. You actually enjoyed something together. It reminds them that the whole evening wasn’t a flop. There were sparks of fun worth exploring.

6. Text At A Time That Feels Random And Fun

A person sitting indoors using a smartphone near a sunlit window.
©Getty Images/Unsplash.com

Skip the “wait 48 hours” nonsense. But there’s also no need to hammer their phone the second you reach your car. Send a message later in the day or the next morning at a time that feels natural. Do it while you’re grabbing coffee or walking out of the gym.

When it pops up at an unexpected moment, it can feel more spontaneous. It feels less “scheduled” and more “hey, I thought of you and wanted to say hi.” That hits different.

7. Send A Quick Voice Note

A person speaking into a smartphone while sitting at a table.
©Andrej Lišakov/Unsplash.com

A short voice note (we’re talking quick) adds flavor that text messages can’t. They get to hear your tone, your laugh, that slight smile sneaking into your words. It’s more real, more alive.

Plus, it shows you’re comfortable enough to show up as your genuine self. No rehearsed lines. No overthinking. Just you, saying hi out loud like a normal person.

8. Add A Little Flirty Energy To Keep Things Exciting

A person wearing a suit holding a coffee cup and a smartphone outdoors.
©Getty Images/Unsplash.com

If the first date felt stiff, now’s your moment to loosen the mood. A playful tease, a “I’m convinced your dog already likes me”, or “Next time, I’m picking the restaurant. I promise zero chair disasters” can make them grin.

Mastering the art of flirting gives off that spark of fun that reminds them you’re attracted to them. Sprinkle it in lightly so things stay lively without going overboard.

9. Drop Their Name Like You Actually Enjoy Saying It

A smiling person sitting on a train talking on a smartphone.
©Getty Images/Unsplash.com

There’s something electric about hearing your own name. Using theirs in a text, like “Hey Maya, hope your morning’s treating you well”, creates a little warmth right away. It’s familiar but respectful.

It shows you’re talking to them, not firing off a copy-paste script you send everyone. (Please don’t be that person.)

10. Let The Conversation Breathe If They Go Quiet

A smiling man standing next to a car while talking over the phone.
©Getty Images/Unsplash.com

If they take a while to reply, stay cool. People have lives, laundry, pets, and random chaos. One slow reply doesn’t mean the story ends. Take a breather instead of double-texting like you’re defusing a bomb.

Give them room to respond on their own time. When they do text back, match their pace, not a rapid-fire interrogation.

11. Suggest A Hangout That Sounds Fun

A person sitting indoors by a window holding a smartphone and looking outside.
©A. C./Unsplash.com

Skip the interview-style dinners for round two. Offer something more playful: “There’s a taco truck with legendary reviews. I need a witness,” or “Let’s try that mini-golf place and pretend we’re pro athletes.”

Fun plans give you both something to look forward to, without the stiff energy of staring across a table under harsh restaurant lighting.

12. Joke About The Awkward Stuff So It Feels Lighter

A person sitting in a car and talking on a smartphone while driving.
©Getty Images/Unsplash.com

Trip over your words? Drop your fork? Accidentally wave at a stranger? Make it part of the joke. “I swear I’m usually 20% less clumsy” can turn an “oh no” into an “ok that’s actually funny.”

Laughing about what happened shows confidence. If you can poke fun at the weird parts, it turns the date from a flop into a quirky memory.

13. Point Out Something Cool You Noticed About Them

A smiling person sitting on a couch while talking on a smartphone.
©Getty Images/Unsplash.com

Pick one detail that stuck with you and send it back to them: their laugh, their style, the way they talked about something they love. Keep it specific so it feels real.

People love being seen in a good way. It’s a compliment that actually has meaning behind it, not something they’ve heard a hundred times.

14. Post Something That Shows You’re Out There Having A Good Time

A group of friends raising glasses of beer for a toast at a bar.
©Getty Images/Unsplash.com

No need for a full highlight reel. A story of your coffee, your walk, your attempt at making pasta can show that your life keeps moving. (Extra points if it’s a little funny.)

It sends a silent message. You have things going on. You’re not sitting in a dark room refreshing your messages like your phone is oxygen.

15. Bring Up The Moment That Made You Both Crack Up

A person looking at their phone while sitting with a skateboard beside them.
©Getty Images/Unsplash.com

Every date has some moment that made both of you laugh, even if it lasted half a second. Mention it again: “Still giggling about the part where the salt shaker tried to escape.”

It puts the spotlight back on the best part of the night. You’re reminding them that you both had fun, which makes another meetup feel like a great idea.

16. Give Them A Little Space Before Popping Back In

A person sitting indoors wearing a plaid shirt and holding a smartphone.
©Getty Images/Unsplash.com

Sometimes a quick pause makes people realize they want more. Step back for a bit, live your life, and later drop a message like “Survived Monday. How’s your day going?”

Space helps interest grow instead of burning out fast. Think of it as a beat in the song, not the end of it.

17. Shoot Them A Chill Message That Sounds Like You

A person walking on a sidewalk while looking at their phone.
©Jayson Hinrichsen/Unsplash.com

No pretending to be someone else. No stiff lines you found online. Text the way you actually talk: “Hey, hope your day isn’t total chaos” hits way better than “Good afternoon, how are you this fine day?”

Be real. Be warm. Be a little playful. Let your personality show up in every word so they think, “Ok, now this is someone I want to see again.”

Dating & Confidence

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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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