101 Text Conversation Starters With A Guy (Flirty, Clever & Cute Ideas)

Struggled with what to text the guy you like? You're not alone. It can be difficult to know where to begin with so many thoughts in mind. But don't worry, we've got you covered. Use these text conversation starter ideas to help you get unstuck or to spark your own creative text messages.


I was impressed by the pants you wore during our last encounter. They would complement my floor nicely.

Share with me something about yourself that you feel is important for me to understand.

Inquire about anything you would like to know.

Hi there beautiful. What's occupying your time at the moment?

Would you rather spend the day exchanging text messages or join me for some fun activities?

Would you mind if I held your hand while we watch a scary film?

What prompted your interest in getting to know me better?

Please send a few pictures of enticing lingerie and seek his assistance in making a selection.

Have you ever been given an unconventional compliment? Can you share what it was?

Squirrels are engaging in mating on my balcony at the moment, and it brought you to mind.

Can you send me a tune that reminds you of me?

Can you send me a tune that reminds you of me?

You appear fantastic today. Rest assured, I am not following you, you simply always look gorgeous.

What would be your chosen pseudonym for adult entertainment?

Do you possess any tattoos? I prefer to discover their location on my own, so please don't reveal their placement.

Can you guess what I have on at the moment?

What do you enjoy having for breakfast the most? Just so I am prepared in advance...

Are you proficient in cooking? Or would you like me to provide a list of my preferred restaurants on UberEats?

Please send an image of an alluring/intimate artwork, accompanied by the caption "thinking of you."

What would be your preferred selection for a Netflix and relax evening?

Can you deduce that I am sending this message while unclothed?


Two truths and a falsehood: I have tried dog food once; I have a fear of moths; I drool while asleep. Can you identify the false statement?

What's the least effective pick-up line that you are aware of?

Which legendary creature embodies your spirit or personality the most?

What is the most peculiar food item that you have consumed?

What is the most unfunny joke you know?

Have you sustained an injury in a nonsensical manner? Can you share the story with me?

What do you consider to be the worst name for a child?

If you could be a type of cheese, which one would you be?

Who would you choose to play you in a movie about your life?

What's the most terrible joke you know using word play? Mine is ______.

Is there anything you enjoy that others dislike or find strange or unpleasant?

What is the most mortifying beverage you have ever requested?

Please describe the most unusual date you have ever been on.

Have you ever been given a terrible gift during a holiday season? Can you share what it was?

What's the most unusual item you've discovered upon moving into a new place?

Do you enjoy singing in the shower? If yes, what's your preferred song to sing?

If you were in a band, what name would you choose for it?

Do you have a preferred word? Mine is _______.

Are there any foods you strongly dislike? I can't tolerate _______.

for deep conversation

rewrite I wonder what the other versions of ourselves in alternate universes are like.

I ponder about the alternate versions of ourselves in other universes.

If you had the opportunity to travel back in time and offer advice to your 12-year-old self, what would it be?

What podcast are you currently interested in and why?

Do you have a preferred book? What is it called?

If a zombie apocalypse were to occur, what role do you think you would play?

What would you consider one of your most indulgent guilty pleasures?

Is there a specific food or beverage that you would deeply mourn if you could never have it again?

Which supernatural entity or concept do you wish was actually real?

What's an uncommon or outdated ability that you possess (or would like to acquire)?

Is there a specific aim or aspiration that you are striving to attain?

Are you content with your current job/career? If you could choose, what would your ideal job be?

If you had the opportunity to spend some time with any historical figure, who would you choose to meet?

What's one aspect of your cultural heritage that you love and cherish the most?

Is there anything related to your cultural background or religious beliefs that you dislike or have differing opinions on?

What's the most unfavorable advice someone has ever given you?

Do you have any remorseful feelings? Would you like to share any of them?

If you could have any superpower, what would it be and why?

If you had the choice to live anywhere in the world, where would you choose to reside?

Do you have a list of things you want to do before you die? If so, what are the top five experiences or goals on it?

Have there been any writers or philosophers who have significantly impacted you over time?

Are you religious or spiritual, if at all?

What type of relationship brings you the greatest happiness and fulfillment?

Are there any unacceptable qualities or behaviors in a partner for you?


Apparently, I have a tendency to talk in my sleep and it's often strange, like saying things like "that cloud really does resemble a bunny".

What brought a smile to your face today?

Here's a photo of my cat/dog/ferret. They want you to know that you're missed.

It's said that a person's preferred ice cream flavor can reveal something about their personality. I like _____. What does that say about me, do you think?

Do you have a go-to comfort food? If so, what is it?

Search for a super cute meme and send it to them, observe their reaction.

FYI, I'm currently checking out your Instagram/Facebook photos avidly.

Which pair of socks do you consider the most thrilling to own?

Send a photo of yourself enjoying some fun with the caption "wishing you were here to join in!"

When I was young, my favorite cartoon was ____. What was your favorite cartoon when you were a child?

Do you like pineapple as a topping on pizza? Yes or no?

Just to let you know, what I appreciate the most about you is ______.

What items would you pack for a picnic if we were to have one?

I wish you could witness the wide grin that spreads across my face every time I receive a message from you.

What would you like me to call you as a pet name?

Do you enjoy dressing up for Halloween?

What is your favorite costume that you've worn so far?

How about we play a game together, like an online version of Scrabble or a similar app?

What are three things that you feel thankful for today?

How much have you changed since you were a child?

to keep him interested

What would you like to do together the next time we meet?

If I offered you the choice of skydiving, scuba diving, or tornado chasing, which one would you go for?

I don't want to boost your ego too much, but I just can't stop thinking about how amazing you smell.

Once upon a time, two incredible individuals crossed paths. Your turn to continue the story...

I'm ticklish. Care to discover where?

You have such a fantastic back. Can't wait to wrap my legs around it.

Is there a type of food that you've always wanted to taste? Would you like to cook it together?

Can you guess what I'm thinking about at the moment?

What would you like to share and teach me?

I miss you. Can we do something to change that?

Confession time: I have a fondness for (unusual food that you enjoy). Are you still interested in continuing our conversation even after knowing that?

If you don't share something negative about yourself, I may continue to constantly think about you.

Which do you prefer, baths or showers? I'm making preparations.

Is there something you've always wanted to do? Let's make it a reality.

I have ordered an excessive amount of food for dinner. Would you like to come over and join me for a meal?

Which Netflix series would you like to watch with me for a binge session?

Do you enjoy adventure? If so, what type of adventure would you like to embark on together?

I'm curious to know what you taste like.

Send me a text tomorrow morning to share what your dreams were like.

As observed, the text conversation starters with a guy can vary from being deep and interesting to light-hearted, enjoyable, and appetizing. Experiment with different types of starters as you get to know your new partner, and see where your conversations lead.