How to Entertain Your Boyfriend over Text

Written by Cher Gopman | Edited by Aly Rusciano

Last Updated: March 10, 2023 References

You want to spend every second with your boyfriend, but there will come a time when you have to be apart. Texting is a great way to keep in touch with him when you can’t be side-by-side, but how can you keep him engaged? What do you do if you don’t know what to type next? Keep reading to learn how you can keep your boyfriend entertained with fun texting games and ice breakers.

This article is based on an interview with our professional dating coach, John Keegan, founder of The Awakened Lifestyle. Check out the full interview here.

1

20 Questions

This classic game will help you learn more about each other in an entertaining way.^{[1]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 19 August 2021.} You can either play the game by thinking of something your boyfriend has to guess in 20 yes or no questions, or ask each other 20 personal questions. Keep the questions light-hearted, playful, and flirty so he doesn’t get bored.^{[2]
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Expert Source

Cher Gopman
Dating Coach
Expert Interview. 17 May 2019.} Try asking your boyfriend these questions to get to know him better:^{[3]
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- “How do you feel about pineapple on pizza?”
- “If you could go anywhere in the world, where would you go?”
- “Who was your first celebrity crush?”

2

Kiss, Marry, Kill

Play a game of hypotheticals with your boyfriend to keep him entertained. If you were standing in front of your three celebrity crushes, what would you do? Text your boyfriend the names of three celebrities and ask him who he would kiss, marry, and kill. Have fun and play along, seeing if you would both choose the same fates for each celebrity.
- Ask your boyfriend why he chose what he did. This is a great way to start a new conversation and have a good laugh!

3

Trivia

Challenge your boyfriend with entertaining questions. A one-on-one game of trivia is not only a great way to have some fun, but can also give you a chance to show off your smarts. Pick a category you both like and find a list of questions online by searching the category with “trivia questions.” Take turns sending each other questions to see who is the trivia master—and no cheating!^{[4]
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- “What was Madonna’s first UK top single?”
- “What singer appeared in the feature film Battleship?”
- “What are the first and last names of all the Friends characters?”

4

Never Have I Ever

This classic sleepover game is a great way to entertain over text. All you have to do is ask your boyfriend a question and set some ground rules. If he has done it, he has to like the message. If he hasn’t done it, he dislikes the message. Now, the questions can be relatively tame, or you can get a little frisky and ask him some sexy questions that’ll make his mind wander. Here are some statements to get you started:^{[5]
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- “Never have I ever had a one night stand.”
- “Never have I ever kissed someone I didn’t know.”
- “Never have I ever crushed on a sibling’s friend.”
- “Never have I ever skinny dipped.”
- “Never have I ever cheated on a test.”

5

Hangman

Keep things entertaining with a favorite spelling game. We’ve all played hangman at some point in our lives. It’s a great way to pass the time and have fun together! Start by thinking of a word your boyfriend will have to guess. Write out a text using underscores to show how many letters are in the word. Let him text you a letter, filling in a blank whenever he gets one right and slowly building an emoji man for each wrong guess. Your text can look something like this:
- 😵
- 👉👈
- 🦶🦶
- _i_iH_w

6

Emoji Decoding

Bring a little mystery to your text convo to keep it entertaining. Send your boyfriend a long line of emojis that play out a famous movie, song, or line—bonus points if you pick his favorite!^{[6]
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Expert Source

Cher Gopman
Dating Coach
Expert Interview. 17 May 2019.} Then sit back and see if he can guess correctly. Here are some movie examples to get you started:
- Ratatouille: 🐀🥘👨‍🍳
- Space Jam: 🪐⛹️‍♂️🐰🐷🐥
- Titanic: 👩‍❤️‍👨🚢🥶

7

Storyteller

Build a story from the ground up to entertain your boyfriend. Text him the opening line of a story. It can be anything you can think of—just keep it one sentence. After you send the opening sentence, your boyfriend sends the next sentence. Feed off each other’s sentences and keep going until you’ve reached the end of your story. Try one of these openings to get things going:
- “Once upon a time, in a land where the people only ate cinnamon rolls, there lived a princess with bright purple hair.”
- “In a galaxy far far away, there was an alien who believed all could be righted with candy bars.”
- “There once was a boy who lived in a tree who wanted nothing more than to live in the sea.”

8

Text Strip Game

A saucy, entertaining game of stripping might be what you both need. When you’re apart from him, you may both be craving physical touch. This is normal in long distance relationships.^{[7]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 29 June 2021.} So, why not play a game that’ll make you both excited to be in each other’s arms again? Ask your boyfriend a question about yourself. If he gets it wrong, he has to strip a piece of his clothing and send a picture.
- Ask him trivia questions to heighten the competitive stacks.
- Be careful when doing anything online. Even if you trust your boyfriend wholeheartedly, you never know if your pictures can fall into the wrong hands.
- Exclude taking pictures all together if you’re uncomfortable or underage. The smartest move to avoid consequences would be to strip and send him a flirty text instead of a photo.

9

Check-In Questions

A simple “How are you?” text can brighten your boyfriend’s day. It seems simple and rather obvious, but your interest in his life can start an entertaining conversation. You may be physically apart, but that doesn’t mean you can’t learn all about his day! Taking the time to talk to each about your days will ultimately bring you closer together. And who knows? Maybe he has a wild story to share!^{[8]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 10 June 2021.}
- “Hey! How was your day?”
- “I missed you today! Did you do anything exciting without me?”
- “How did that test go?”

10

Flirty Messages

Toss a cheeky compliment into your text convo every now and then.^{[9]
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John Keegan
Dating Coach
Expert Interview. 29 June 2021.} This will keep him entertained and have him missing you even more. A playful and flirtatious compliment here and there can take the boring out of long distance relationships.^{[10]
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Expert Source

Cher Gopman
Dating Coach
Expert Interview. 17 May 2019.}
- Tap into your imagination and experiment with roleplaying and sexting. This is a great way to flirt and fulfill both of your sexual needs.
- “Not gonna lie, you’re always on my mind.”
- “Why are you so cute? 😉”

11

Fun Photos

Snap a pic of what you’re doing and send it to him. Your boyfriend will appreciate you thinking of him and is bound to be entertained by whatever you send him. You can keep it friendly, snapping a selfie of you cooking dinner, or you can get a little spicy and send a pic of you posing in a sexy outfit.^{[11]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 19 August 2021.}
- “Thinking of you!”
- “Wishing you were here to devour this cake with me 😜”
- “Like my new outfit? 😏”

12

Common Interests

Connect with something that entertains you both. Does he have a favorite movie, book, or band? Find one of his interests you're interested in and dive headfirst into it. Say you’re watching a movie he loves. Text him your live reactions to plot twists and scenes that blew your mind. He’s sure to be entertained by your frantic messages!^{[12]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 19 August 2021.}
- “So I just watched WandaVision, and I can’t believe you put me through that.”
- “HE DID WHAT??”
- “This book has killed me and it’s all your fault.”

Expert Q&A

Question

How do you flirt through text?

Cher Gopman
Dating Coach
Cher Gopman is the Founder of NYC Wingwoman LLC, a date coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Cher is a Certified Life Coach, a former psychiatric nurse, and her work has been featured on Inside Edition, Fox, ABC, VH1, and The New York Post.

Cher Gopman

Dating Coach

Expert Answer

If you are trying to flirt through text messages, use emojis to keep the chat lighthearted and fun. However, you don't want to overuse them, because that'll come off as too eager. Make sure to keep the questions not boring. Make sure the conversation is always moving forward, ask questions, you don't want to stick on one topic for too long, it can become boring for the other person. Don't be afraid to send a photo of somewhere that you're located, something around you that's interesting, or something that reminds you of the person.