Fun and Freaky Questions to Ask Your Boyfriend

Written by Jacqueline Hellyer | Edited by Aly Rusciano

Last Updated: September 17, 2022 References

So, you want to spice things up with your boyfriend? You’re in the mood and want to get him feeling it too without it getting awkward. There’s no shame in talking or texting sexy to your boyfriend, especially when you want to have some fun! Maybe you want to up the antics with some flirts or juicy questions that’ll make his mind wander. Either way, we’ve compiled a list of freaky questions you can ask your boyfriend.

This article is based on an interview with our licensed psychosexual therapist, Jacqueline Hellyer, founder of The Love Life Blog and The LoveLife Clinic. Check out the full interview here.

1

“Do you want to know what I’m wearing?”

Text your boyfriend this flirtatious question to make his mind wander. You could be sitting at home in your comfiest pjs or trying on your newest lingerie. Either way, let him know you’re thinking about spending some time with him later.
- Add a “😏” or “😘” to the end of your text to make it extra flirty.
- To make him even more crazy, send him a picture!
- Feeling extra sexy? Text him “Guess what color my lingerie is?”

2

“What is your favorite position?”

Talk to your boyfriend about what makes sex fun for him. Licensed psychosexual therapist Jacqueline Hellyer stresses the importance of "communicating with each other on and off the bed to know what’s working." If you’re comfortable, explore his favorite position with him, and who knows? Maybe you’ll find something new you like too!

3

“What movie scene turns you on?”

This can be a casual or sexy question. Perhaps you’re simply curious as you’re curled up next to your boyfriend on the couch, or you’re looking for a way to spice up the bedroom. His answer to this question can open a playful conversation and ease you both into talking more about your sexualities.^{[1]
X
Research source}

4

“What’s one thing I can do right now that’ll drive you wild?”

See what you can do to get your boyfriend in the mood with this question. Maybe he just got home and you’re ready to take him then and there, or you’re texting him at work and can’t stop thinking about him. Either way, drive him crazy with this freaky question and let your imaginations run wild.^{[2]
X
Research source}

5

“Do you check me out when I walk away?”

This cheeky little question can have your boyfriend thinking about your backside. Let his mind wander to you, which will hopefully get you in the mood. Add a little wink to the question, a sexy pose, or a “😏” if you’re texting him.^{[3]
X
Research source}

6

“What’s your favorite part of my body?”

This is a playful question you can ask your boyfriend in bed or through text. Get a little frisky and have him touch the body part, as long as you're comfortable, or text him back a flirty reply telling him to get ready to see it later.^{[4]
X
Research source}

7

“Have you ever had a dream about me?”

Ask your boyfriend this question when things are calm. Maybe you’re resting your head on his chest after a pleasurable night, or are curled up with him on the couch. Fill any silence with this sweet question to get him blushing.

8

“What’s your sexiest fantasy?”

Explore your boyfriend’s deepest sexual dreams with this freaky question. This is a great way to learn more about him and get an idea of what he may like in the bedroom. Is he into BDSM? Does he have a sex fantasy with food? Not only can this give you ideas on how to up the antics next, but it can help you both feel more comfortable talking about sex.^{[5]
X
Expert Source

Jacqueline Hellyer
Licensed Psychosexual Therapist
Expert Interview. 15 October 2021.}
- Be upfront with your boyfriend and tell him what you are and are not comfortable with. Honesty is, and always will be, the best policy, especially when it comes to relationships.

9

“Do you have any kinks or fetishes?”

Get freaky by putting everything out in the open. There’s no shame in having a few sexual quirks, so why not ask your boyfriend if he has any? It’s important to talk openly with your partner about sex, especially if they like doing things a bit differently than you.^{[6]
X
Expert Source

Jacqueline Hellyer
Licensed Psychosexual Therapist
Expert Interview. 15 October 2021.}
- Embrace your sexuality and be open with your boyfriend about what you like and dislike. Not only will this help you be honest with each other, you’ll know what each other likes, leading to even more fun.^{[7]
  X
  Expert Source
  
  Jacqueline Hellyer
  Licensed Psychosexual Therapist
  Expert Interview. 15 October 2021.}

10

“Where’s the weirdest place you’d want to have sex?”

Start a sexy conversation with your boyfriend with this freaky question. Each time will be different. Sex with your boyfriend is more than itching a scratch, it’s creating an experience of fun and pleasure that you both can enjoy.^{[8]
X
Expert Source

Jacqueline Hellyer
Licensed Psychosexual Therapist
Expert Interview. 15 October 2021.} So, let your imaginations run wild and see if you both have the same fantasies. And who knows? Maybe you’ll find a new favorite spot!
- Sex is natural, so don’t be afraid to talk to your boyfriend about it! You do it together, so why hold back your curiosities?

11

“Would you rather have sex in the shower or in a pool?”

Challenge your boyfriend to a little game that’ll bring out his sexy quirks. A frisky, quick game of “Would You Rather” can put you both in the mood all while learning more about each other’s sexuality. Keep things classy, or dive into wildly sexy scenarios. Have fun and don’t be afraid to ask him anything! Here are some other questions you can ask:^{[9]
X
Research source}
- “Would you rather go to the grocery store in your underwear or go to the beach nude?”
- “Would you rather receive a sexy text message or a sexy nude photo?”
- “Would you rather kiss someone in the dark or make out in a public setting?”
- “Would you rather have sex in a smelly bathroom or on a stain-covered bed?”

12

“What do you like most about when we have sex?”

Honesty is always the best policy, especially when it comes to being intimate. Don’t be afraid to ask your boyfriend what he likes and dislikes about having sex—and make sure to ask yourself the same thing too! The sexual experience will be even better just by talking about what it is you both want. Go through the motions physically and verbally.^{[10]
X
Expert Source

Jacqueline Hellyer
Licensed Psychosexual Therapist
Expert Interview. 15 October 2021.}

13

“How do you feel when we have sex?”

Communication is a key part in any relationship. Being in tune with what you’re feeling before, during, and after sex can help you get the most out of your time together. Ask your boyfriend how he feels about sexy time, and do the same to yourself. Focus on inward feelings rather than what you’re outwardly experiencing. Try asking yourself these questions the next time you’ve had or are thinking about having sex:^{[11]
X
Expert Source

Jacqueline Hellyer
Licensed Psychosexual Therapist
Expert Interview. 15 October 2021.}
- “What am I feeling right now?”
- “What do I want to hear?”
- “What am I expressing?”