100 Secret Santa Questions to Make Gift Swaps Fun and Personal

Secret Santa questions add a twist of curiosity and connection to any holiday exchange. It’s easy to get caught up in the pressure of finding the “perfect” gift—especially for someone you might not know that well. But that’s exactly where the right questions can help. Secret Santa isn’t just about presents; it’s about presence. These questions are designed to break the ice, give subtle (or obvious) hints, and add a little joy to every part of the process. Whether you’re organizing a swap with friends, coworkers, or family, these questions turn guesswork into gift-worth.

Fun & Lighthearted Icebreakers

These questions are designed to warm people up. Whether you’re organizing a workplace gift swap or a festive gathering with friends, this section makes it easy to break the ice. The questions are silly, easy to answer, and reveal just enough personality to spark conversation or laughter—without getting too personal or serious. Think of them as wrapping paper for deeper connections.

1. What’s your guilty-pleasure snack?

2. Do you believe in re-gifting?

3. If you were a holiday drink, what would you be?

4. What’s your go-to comfort food?

5. Are you more of a scarf person or fuzzy socks person?

6. What’s your favorite holiday movie quote?

7. What’s your “I’ll never say no to this” treat?

8. What cartoon character would you want as a roommate?

9. What’s a hobby you’ve always wanted to try but haven’t?

10. Do you own anything with glitter on it?

11. What song gets stuck in your head way too easily?

12. What’s your favorite way to spend a lazy Sunday?

13. What was your favorite childhood toy?

14. What holiday candy do you avoid at all costs?

15. What’s your snack of choice for a movie night?

16. Would you rather receive something edible or wearable?

17. Are you a scented candle person or a room spray fan?

18. What’s the weirdest item currently in your bag or desk?

19. If you had a signature scent, what would it smell like?

20. Would you rather get something practical or totally pointless?

This or That: Holiday Edition

Quick and festive, this-or-that questions make it easy for participants to choose between two holiday-themed options—no overthinking required. They’re perfect for groups where people may not know each other well or just want a fast, fun way to get into the spirit. Plus, the answers often offer subtle gift clues (like whether to buy them cocoa or cookies).

1. Hot cocoa or eggnog?
2. Gingerbread or sugar cookies?
3. Snowball fight or sitting by the fire?
4. Wrapping paper or gift bags?
5. Elf or Home Alone?
6. Ugly sweater or matching pajamas?
7. Real tree or artificial tree?
8. Christmas Eve or Christmas morning?
9. Silent Night or Jingle Bell Rock?
10. Candy canes or peppermint bark?
11. Ice skating or sledding?
12. Secret Santa or White Elephant?
13. Classic carols or modern remixes?
14. Holiday baking or holiday crafting?
15. Online shopping or in-store chaos?
16. Lights everywhere or minimalist decor?
17. Red and green or blue and silver?
18. Snowy cabin or beach vacation?
19. Giving gifts or receiving them?
20. Santa hat or elf ears?

Gift Guide Hints in Disguise

This section is ideal if you’re trying to buy a gift but don’t want to directly ask someone what they want. These questions are sneakily specific—designed to give just enough insight into someone’s tastes, habits, and preferences without ruining the surprise. They’re especially useful for Secret Santa setups where anonymity is still part of the fun.

1. What’s one small thing that would make your day better?
2. What’s your go-to self-care ritual?
3. What’s something you never buy for yourself but love getting?
4. What’s your favorite scent in winter?
5. What’s something you always keep at your desk or in your bag?
6. What kind of gift makes you feel the most seen?
7. What’s your favorite type of mug or glass?
8. What color do you naturally gravitate toward?
9. What’s one thing you wish you had more of this time of year?
10. If you could only receive one type of gift forever, what would it be?
11. What’s your favorite kind of cozy accessory?
12. What’s your idea of the perfect 10-minute break?
13. What’s something you secretly collect (even if it’s just mentally)?
14. Do you prefer experiences or objects as gifts?
15. What’s a kitchen gadget you’ve always wanted?
16. What’s one thing on your wish list that costs under $20?
17. What’s something you wish people knew you liked?
18. What do you always appreciate but never expect?
19. What’s your preferred kind of indulgence: sweet, salty, or sensory?
20. What’s a book, game, or item you’d love to be surprised with?

Unexpected and Quirky

Sometimes the best answers are the weird ones. These questions are for the oddballs, the inside jokers, and the people who love a little chaos in their Christmas cheer. Use this section to make people laugh, raise eyebrows, or share the kinds of answers that lead to unexpectedly perfect gifts—like a novelty spatula or a cat-themed coloring book.

1. What’s the weirdest item on your dream wishlist?
2. If your pet had to pick your gift, what would it be?
3. What fictional world would you want your gift to come from?
4. If you were a gift, how would you be wrapped?
5. What’s a totally useless item you’d be delighted to receive?
6. What would your villain alter ego want for the holidays?
7. What’s one thing you own that would confuse someone from the past?
8. What’s a novelty item you secretly love?
9. What object feels like “you” but no one would guess it?
10. What’s something festive you’d never admit to liking?
11. What’s your unofficial holiday motto?
12. What’s your inner eight-year-old begging for this year?
13. If your holiday spirit was an object, what would it be?
14. What’s a totally random thing you think everyone should own?
15. What’s a “joke gift” you’d secretly treasure?
16. What kitchen item are you irrationally excited about?
17. What’s something ridiculous that always makes you laugh?
18. What’s a household item you weirdly have opinions about?
19. If your personality could be bottled, what would it smell like?
20. What’s one gift you’d want just for the story?

Heartfelt & Reflective

If your group is close-knit—or you’re ready to take the gift exchange a little deeper—this section is where the real connections happen. These questions help people reflect on the year, on relationships, and on what truly matters to them. They’re perfect for creating moments of genuine emotion, appreciation, or even healing during the holidays.

1. What memory from the holidays always makes you smile?
2. What’s something you’re proud of this year?
3. What tradition do you hope to never let go of?
4. Who taught you how to give thoughtful gifts?
5. What does a “perfect” gift mean to you?
6. What small act of kindness still sticks with you?
7. What makes you feel most cared for?
8. What’s something you’d never ask for but really want?
9. What’s the most meaningful gift you’ve ever received?
10. What’s something simple that makes you feel at peace?
11. What do you secretly hope someone will notice about you?
12. What makes you feel instantly comforted?
13. What’s a sound, smell, or song that makes it feel like the holidays?
14. What’s something you’ve learned about yourself this year?
15. What’s one thing you’re grateful for that money can’t buy?
16. If someone wanted to make you feel understood, what would they give you?
17. What’s a moment from this year that you’ll never forget?
18. What does “thoughtful” mean to you in gift-giving?
19. What’s your love language—and how does it show up around the holidays?
20. What kind of gift tells you someone really knows you?