The Best Flirty Ways to Ask “How Was Your Day”

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Sarah Koch


Wondering how to ask your crush or partner “How was your day?” in a fun, flirty way? Tired of the same old boring small talk? I’ve got you covered.

After a dull conversation with my new dating interest that went nowhere, I decided there must be better, more engaging ways to show interest and learn about someone’s day.

Below I’m sharing 30+ flirty, witty options to spice up this common question and take your bonding to the next level. If you want a fun, lively discussion that creates sparks, try out some of these playful alternatives. Read on for plenty of inspiration!

How Was Your Day

30 Flirty & Fun Ways to Ask About Someone’s Day

Before jumping straight into the list, here’s the key to making these work: say them with a wink, smile or raise of the eyebrows. A little humor and double meaning goes a long way. Now let’s get creative!

  • Tell me something naughty you did today
  • What was the highlight of your day?
  • Anything fun or exciting happen since we last talked?
  • Were you a good girl/boy today?
  • Did you accomplish anything awesome?
  • What adventures did you get up to today?
  • Did you have any mischief planned for today?
  • What was the most interesting part of your day?
  • Did anyone give you trouble today?
  • Did you spread any happiness around today?
  • Were people nice to you or did you have to set them straight?
  • Did you get to do anything you love today?
  • Have any secrets to share about your activities today?
  • What was your favorite part of the day?
  • Did you take a chance on anything exciting?
  • Were you a rebel today or did you play by the rules?
  • Any drama happen that you need to vent about?
  • Tell me one awesome, amazing thing that happened.
  • Were people nice to you today or just annoying?
  • Did anyone make you laugh a lot today?
  • Have any juicy stories to tell me about today?
  • What put the biggest smile on your face today?
  • Did you spread any kindness or joy to others today?
  • Were you productive today or just relaxed?
  • Did you learn anything new or have a fresh experience?
  • What surprised you the most about today?
  • Did you feel appreciated today?
  • Tell me something sweet you did or saw.
  • Anything frustrating or challenging happen?
  • What made you proud about how you showed up today?
  • Did you feel totally in the zone or just out of it?

I hope those give you plenty of fun new ideas to try out next time you want to connect with someone special and learn about their day! Remember to say them playfully and not take yourself too seriously. A lighthearted, inquisitive approach is the key to keeping things positive.

Funny Ways to Ask About Their Day

Here are some humorous ways to inquire about their daily activities that are sure to get a smile:

Also Read: Witty Comebacks for “Is it Raining Today?”

Flirty Ways to Find Out About Their Day

These responses take a more romantic angle:

Also Read: Best Ways to Respond When a Guy Says He Wants to Spoil You

Understanding Their Responses

Now that you have some ideas for spicing up the simple “How was your day?” question, let’s explore how to interpret the answers you receive.

If their response is vague like “It was fine” or “Nothing special happened,” try asking for one highlight even if it was something small that made them smile. Getting specifics helps move the conversation forward in a more meaningful way.

Flirty responses indicating they wished you were there are very positive signs. Play off of whatever romantic notions they bring up to continue building intimacy through imagination and shared daydreams.

Following Up Based on Their Reaction

After your creative icebreaker leads to them opening up about their day, you’ll want to actively listen and respond in an engaged way.

If they sound stressed, empathize and offer encouragement. If they’re venting frustrations, validate their feelings. When they share accomplishments big or small, congratulate and compliment them.

Essentially tailor your follow up questions and reactions based on the tone set by how they respond. Show genuine interest, validate any expressed emotions, and sprinkle in supportive or impressed comments.

This attentive listening strengthens your connection and the comfortability to confide in one another. It also demonstrates your care for their well being.

Turning the Conversation Flirty

Once you’ve actively listened and shown support after your playful opener, you can steer things in a more romantic direction with comments like:

Flirty invitations demonstrate your desire to be physically present for them. If said casually and lightheartedly, they can open the door to planning a fun date while learning more about each other.

In addition to using the sentences above to ask “How Was Your Day,” there are other ways we can make the conversation more interesting: use die-cut stickers.

You can print the sentences you use to ask about their day or the words you want to say to them on the stickers. Give them these stickers as a gift, or use these stickers to decorate the gift you are giving them, which will allow you to make a deep impression on them and strengthen your connection.

Don’t be shy and ask your crush “How Was Your Day” bravely!

Also Read: Flirty Replies to Where Are You

How to Ask “How Was Your Day” to a Guy in Flirty Way?

If you want to spice up your conversation with a guy, you can try asking him “How was your day” in a flirty way. Here are some tips on how to do that:

Use emojis. Emojis can add some fun and personality to your text, and show him that you’re feeling playful. For example,

you can send him a wink , a smile , or a kiss to make him feel special.

Add a compliment. A compliment can boost his confidence and make him more interested in you. For example,

you can say “How was your day, handsome?” or “How was your day, you amazing human being?” to show him that you admire him.

Be suggestive. If you want to turn up the heat, you can be more suggestive with your text. For example,

you can say “How was your day, babe? I can’t stop thinking about you” or “How was your day, hottie? I wish I was there with you” to make him think of you in a more intimate way.

Be curious. A good way to keep the conversation going is to be curious about his day and show him that you care. For example,

you can say “How was your day, sweetie? Tell me everything” or “How was your day, cutie? I want to hear all about it” to encourage him to open up to you.

Also Read: Flirty Responses When Someone Asks “How Was Your Day”

How to Ask “How Was Your Day” to a Girl in Flirty Way?

If you want to spice up your conversations with a girl, you might want to ask her how her day was in a flirty way. Here are some tips on how to do that:

Use emojis and gifs to express your emotions and reactions. For example, you can send a wink or a heart to show your interest and appreciation.

Compliment her on something she did or wore that day. For example, you can say “You looked amazing in that dress today” or “You rocked that presentation today”.

Ask open-ended questions that invite her to share more details and feelings. For example,

you can say “What was the best part of your day?” or “How did you feel when you did that?”

Tease her playfully about something she said or did. For example,

you can say “You’re such a nerd for liking that movie” or “You’re so brave for trying that food”.

Use humor and sarcasm to make her laugh and challenge her. For example,

you can say “Wow, you’re so lucky to have such a boring day” or “I bet you had a lot of fun doing that”.

In Closing

Spicing up the simple “How was your day?” question can bring some creativity and humor to everyday conversations. Paying close attention to your crush or partner’s response, then following up thoughtfully and supportively, strengthens your connection. From there, injecting flirtatious remarks can help move things to the next level.

I hope these tips and examples helped provide ideas for making this common inquiry more playful and engaging. Don’t be afraid to put your own spin on things too! A little effort and attention to detail can go a long way when looking to turn basic small talk into deeper flirty banter.

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