30 Flirty Ways to Ask “How Was Your Day?” 😉

Sophie Harris

Ever wondered how to make asking about someone’s day a bit more exciting? Sometimes a simple “How was your day?” just doesn’t cut it.

Imagine texting your crush after a long day and making them smile with a flirty twist on that routine question.

It’s a great way to show you care and add a dash of charm to your conversation. Whether you’re looking to impress someone new or keep the spark alive in a budding romance, these flirty ways to ask “How was your day?” will make your interactions more engaging and memorable.

Dive in and find the perfect line to make their day a little brighter!


1. “Hey, I’ve been thinking about you all day. How was it?”

  • Story: After a long day at work, I texted someone I was interested in, “Hey, I’ve been thinking about you all day. How was it?” It made them smile and opened up a fun conversation.
  • When to use: When you want to express genuine interest and start a flirty conversation.
  • When not to use: If you’re still in the early stages of getting to know someone and want to keep things more casual.

Example:
You: “Hey, I’ve been thinking about you all day. How was it?”


2. “So, did you have a good day, or was it missing something—like me?”

  • Story: I used this line with someone I had just started dating. It was a playful way to suggest I was thinking about them.
  • When to use: When you’re comfortable with each other and want to add a touch of humor.
  • When not to use: If you’re unsure about their sense of humor or if it’s too early in your relationship.

Example:
You: “So, did you have a good day, or was it missing something—like me?”


3. “Tell me all about your day. I’m all ears (and maybe a little bit of jealousy)!”

  • Story: I sent this to a crush after they mentioned having a busy day. It was a fun way to show interest while keeping things light.
  • When to use: When you want to be playful and engaging, and there’s already a good rapport.
  • When not to use: If you’re trying to be more serious or if the person is having a tough day.

Example:
You: “Tell me all about your day. I’m all ears (and maybe a little bit of jealousy)!”


4. “Did you miss me today, or was it just me who missed you?”

  • Story: After an entire day apart, I texted this to a person I was seeing. It was a cheeky way to let them know they were on my mind.
  • When to use: When you’ve been apart for a while and want to add a flirty touch.
  • When not to use: If the person is feeling down or if it’s not appropriate to show vulnerability.

Example:
You: “Did you miss me today, or was it just me who missed you?”


5. “I bet your day was good, but I bet it would have been better if we were together!”

  • Story: I sent this to someone I was dating, suggesting that their day could have been improved with my company. It was playful and engaging.
  • When to use: When you want to suggest your presence could enhance their day.
  • When not to use: If the person is dealing with something serious or if the timing isn’t right.

Example:
You: “I bet your day was good, but I bet it would have been better if we were together!”


6. “How was your day? Did it include any thoughts about me?”

  • Story: I texted this to a person I was flirting with, adding a hint of curiosity and flirtation.
  • When to use: When you’re comfortable with each other and want to be a bit playful.
  • When not to use: If you’re unsure how the other person feels about your flirtation.

Example:
You: “How was your day? Did it include any thoughts about me?”


7. “So, what was the highlight of your day? I’m guessing it was thinking about me!”

  • Story: I used this line to make a light-hearted guess about what made their day special.
  • When to use: When you want to be fun and cheeky, and you know they’ll appreciate the humor.
  • When not to use: If the person is having a rough day or if it’s too early in your relationship.
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Example:
You: “So, what was the highlight of your day? I’m guessing it was thinking about me!”


8. “Was your day as amazing as you are?”

  • Story: I sent this to someone I was interested in, combining a compliment with a casual question about their day.
  • When to use: When you want to give a compliment while asking about their day.
  • When not to use: If the compliment might come off as too much too soon.

Example:
You: “Was your day as amazing as you are?”


9. “How did your day go? I’m eager to hear about it—especially if it involves me!”

  • Story: I sent this text to keep the conversation engaging and flirty, hinting that I wanted to be part of their day.
  • When to use: When you want to express interest and make the conversation more engaging.
  • When not to use: If the person is busy or if you need to keep things more casual.

Example:
You: “How did your day go? I’m eager to hear about it—especially if it involves me!”


10. “Tell me everything about your day. I need to know if you were as adorable as usual!”

  • Story: I used this line to combine curiosity with a compliment, making it playful and flirty.
  • When to use: When you’re already comfortable with each other and want to add a touch of charm.
  • When not to use: If the person is not yet used to your flirtatious style.

Example:
You: “Tell me everything about your day. I need to know if you were as adorable as usual!”


11. “I’m betting your day was great, but I’m still missing you!”

  • Story: I sent this message to someone I was dating to show I was thinking about them and missed their company.
  • When to use: When you want to convey that you miss them and are thinking about them.
  • When not to use: If the person is feeling down or if it’s not appropriate to show vulnerability.

Example:
You: “I’m betting your day was great, but I’m still missing you!”


12. “How was your day? Any exciting stories you want to share with me?”

  • Story: I asked this to encourage a fun conversation and show that I was genuinely interested in their experiences.
  • When to use: When you want to keep the conversation engaging and interesting.
  • When not to use: If you’re in a rush and need a quicker response.

Example:
You: “How was your day? Any exciting stories you want to share with me?”


13. “I bet you made the day shine a little brighter. How was it?”

  • Story: I texted this to someone I was seeing, combining a compliment with a question about their day.
  • When to use: When you want to compliment them while asking about their day.
  • When not to use: If you don’t want to seem overly flattering or if you’re unsure of their reaction to compliments.

Example:
You: “I bet you made the day shine a little brighter. How was it?”


14. “How did your day treat you? I’m sure it was better because of you!”

  • Story: I sent this to add a flirty compliment while inquiring about their day.
  • When to use: When you want to combine a friendly question with a compliment.
  • When not to use: If you want to keep the conversation more straightforward or if they might find it too much.

Example:
You: “How did your day treat you? I’m sure it was better because of you!”


15. “I’m dying to know—how was your day without me?”

  • Story: I used this line to add a playful twist to asking about their day, suggesting that they missed my presence.
  • When to use: When you want to be playful and tease them a bit.
  • When not to use: If you’re still getting to know each other or if the person prefers straightforward communication.
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Example:
You: “I’m dying to know—how was your day without me?”


16. “I hope your day was as great as the smile I’ve been imagining on your face!”

  • Story: I texted this to someone I was seeing, combining a compliment with a question about their day.
  • When to use: When you want to make them smile and show that you’re thinking about them.
  • When not to use: If you’re trying to keep things more casual or if they prefer less overt flirtation.

Example:
You: “I hope your day was as great as the smile I’ve been imagining on your face!”


17. “What was the best part of your day? I have a feeling it was thinking about me!”

  • Story: I sent this to tease a bit while showing genuine interest in their day.
  • When to use: When you want to be playful and show that you’re thinking about them.
  • When not to use: If they’re not in the mood for teasing or if you don’t want to seem too forward.

Example:
You: “What was the best part of your day? I have a feeling it was thinking about me!”


18. “How was your day? Did you manage to miss me as much as I missed you?”

  • Story: After a day apart, I texted this to let them know I was thinking about them and missed them.
  • When to use: When you want to express that you’ve been missing them and make them feel special.
  • When not to use: If the person might not be in the mood for a sentimental message.

Example:
You: “How was your day? Did you manage to miss me as much as I missed you?”


19. “Was your day as fantastic as the thought of seeing you soon?”

  • Story: I used this line to show that I was looking forward to seeing them and to add a flirty touch.
  • When to use: When you’re excited about seeing them and want to convey that through your question.
  • When not to use: If you’re still building a relationship and want to keep things more casual.

Example:
You: “Was your day as fantastic as the thought of seeing you soon?”


20. “How was your day? Did you have any moments that made you wish I was there?”

  • Story: I texted this to someone I was dating to show that I was thinking about how they spent their day.
  • When to use: When you want to be playful and suggest you’d have enjoyed being with them.
  • When not to use: If the person is busy or if you’re unsure how they feel about this kind of flirtation.

Example:
You: “How was your day? Did you have any moments that made you wish I was there?”


21. “So, tell me, did you have a day as charming as you are?”

  • Story: I sent this to someone I was interested in, mixing a compliment with a question about their day.
  • When to use: When you want to compliment them and ask about their day in a flirty manner.
  • When not to use: If you’re still in the early stages of dating and prefer to keep things simpler.

Example:
You: “So, tell me, did you have a day as charming as you are?”


22. “How did your day go? I’m hoping it was filled with thoughts of me!”

  • Story: I used this line to combine curiosity about their day with a playful hint that I was on their mind.
  • When to use: When you want to be a bit cheeky and show that you’re thinking about them.
  • When not to use: If the person prefers a more straightforward approach.

Example:
You: “How did your day go? I’m hoping it was filled with thoughts of me!”


23. “Was your day busy, or did you have time to think about how amazing I am?”

  • Story: I sent this message to add a flirty twist while asking about their day’s busyness.
  • When to use: When you want to tease them and keep the conversation light-hearted.
  • When not to use: If you’re looking for a more serious conversation or if they’re stressed.
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Example:
You: “Was your day busy, or did you have time to think about how amazing I am?”


24. “How was your day? I bet it was great, but not as great as my day imagining you!”

  • Story: I used this line to show that I was thinking about them and to add a touch of flirtation.
  • When to use: When you want to let them know they were on your mind and add a playful element.
  • When not to use: If you want to keep the conversation more neutral.

Example:
You: “How was your day? I bet it was great, but not as great as my day imagining you!”


25. “I’m dying to know—how did your day measure up to the excitement of hearing from me?”

  • Story: I texted this to make them smile and hint that I was excited to hear from them.
  • When to use: When you want to convey enthusiasm and keep the conversation engaging.
  • When not to use: If you’re trying to keep things more laid-back or if the person prefers simplicity.

Example:
You: “I’m dying to know—how did your day measure up to the excitement of hearing from me?”


26. “How was your day? Any fun stories that involve me?”

  • Story: I used this to keep the conversation fun and engaging, suggesting that I’d love to be part of their stories.
  • When to use: When you want to be playful and invite them to share their experiences.
  • When not to use: If you’re looking for a more serious conversation or if they’re not in the mood for flirting.

Example:
You: “How was your day? Any fun stories that involve me?”


27. “I hope your day was as wonderful as the thought of our next meeting!”

  • Story: I sent this text to combine a compliment with anticipation for the next time we’d see each other.
  • When to use: When you’re looking forward to seeing them and want to convey that excitement.
  • When not to use: If the person might find it too forward or if you’re not yet at that level of intimacy.

Example:
You: “I hope your day was as wonderful as the thought of our next meeting!”


28. “How was your day, and did you find time to miss me a little?”

  • Story: I used this line to suggest that I was on their mind and to add a touch of flirtation.
  • When to use: When you want to express that you missed them and see if they felt the same.
  • When not to use: If you’re unsure how they feel about such direct expressions of affection.

Example:
You: “How was your day, and did you find time to miss me a little?”


29. “So, how was your day? I’m hoping it was full of moments that made you smile—like thinking about me!”

  • Story: I texted this to add a flirty touch to asking about their day, suggesting that I hoped they had moments that involved me.
  • When to use: When you want to be charming and hint that you were on their mind.
  • When not to use: If the person prefers more straightforward or less flirtatious conversation.

Example:
You: “So, how was your day? I’m hoping it was full of moments that made you smile—like thinking about me!”


30. “How was your day? Did it bring any thoughts of how amazing it would be to be with me?”

  • Story: I used this line to playfully suggest that my presence would have made their day better.
  • When to use: When you want to be flirty and suggest that you’d enhance their day.
  • When not to use: If you’re still establishing the relationship or if you’re unsure how they’ll receive the flirtation.

Example:
You: “How was your day? Did it bring any thoughts of how amazing it would be to be with me?”

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