50+ Questions to ask your FWB

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By: Naveen B

It’s better to be safe than sorry. Friends with benefits relationship is fun but at the same, it’s risky to involve in such casual encounters.

In order to avoid n#sty surprises and avoid hurting your partner, here are some questions you need to ask your friend before entering into such relationships: 

Questions to ask your FWB


Here is the list of questions to ask a FWB

1. What are your intentions? Ask yourself if you really want a relationship or if you’re using each other as a stepping stone in life.

If your intention is to actually get serious, you should ask them about their intentions as well. Make sure that you’re on track before things become complicated. 

2. Why do you want an FWB? It might seem like it’s all fun and games, but there has to be some reasoning behind why each of you chose one another as an FWB in order for it work out in the long run.

3. What are your boundaries? Talk about what s#xually they are comfortable doing and make sure they know yours too!

4. What if one of us changes their mind? You might not be ready for a full-blown relationship, but you never know what life may throw at you.

If things don’t work out in either way, make sure both of you are aware of how and when to back out of your FWB status gracefully.

It’s best to end things on good terms, as opposed to making a big deal about it later on down the road!

5. What is allowed and not allowed in your relationships? Communication is key! Don’t assume that just because something was okay last week, it will be okay again next week or even next month.

Be honest about what you’re comfortable doing; otherwise, people tend to feel like they can get away with anything which creates serious trust issues.

Also read: 31 Questions to ask yourself before becoming friends with benefits

6. How will we avoid getting attached? Again, communication is key! If either of you starts feeling too much for one another, it’s best to talk about it before things get out of hand.

It’s far better to discuss these feelings beforehand than find out after you start developing serious feelings for one another that they didn’t feel as strongly as you did or have no intention of letting a relationship happen at all.

This can be especially damaging if one person was hoping that their friendship would turn into something more.

While the other had no intentions of pursuing anything further than just being a friend and trying to win them over anyway regardless of how they felt towards that person.

7. What happens if you guys aren’t as compatible as you thought? No one is perfect and it’s unlikely that two people will be on exactly the same page when it comes to what they want out of their relationships or how they feel about certain things.

If either of you isn’t happy in your FWB situation, make sure that you’re able to talk about it without anyone feeling like they are walking on eggshells in order for it work out.

And remember, don’t take them personally; there’s a chance that your personalities just won’t mesh well together no matter how much you love each other. It’s better for both of you if you accept that sooner rather than later.

8. What does our future look like? It’s impossible to know what life has in store for you, but that doesn’t mean that you shouldn’t be able to share your dreams for your lives as well as find out what they want too.

If both of you have different views on where things will go or how it will work out, make sure that all these differences are discussed before moving forward.

You don’t want one person to get hurt and you don’t want anyone getting their hopes up if there’s no chance of either party getting what they want out of it.

For example, I wouldn’t suggest being an FWB with someone who is only in town temporarily versus someone who has no intention of leaving any time soon.

Related: 150+ Friends with benefits questions

9. What is your STD status? Again, it’s probably not something you want to talk about right away, but you do need to have a plan in place in case something happens.

Whether that means getting tested together or at different times (just make sure you can be mature about it if things don’t match up!), having a game plan ensures that neither of you will be caught off guard by what may come.

Having no information on whether one or both of you are free from s#xually transmitted diseases will only cause unnecessary drama.

Chances are that if either one of you is interested in an FWB situation long-term, at least one person has had more than just their fair share of s#xual partners which increases your odds for contracting something n#sty.

10. Is what we’re doing okay? I’ve known plenty of people who did things in secret that were completely different from what they were doing when their partner wasn’t around or vice versa! 

Both partners need to be comfortable with what you are doing and if either one of you is having a hard time, talk about it.

Having an open line of communication helps keep everyone on even grounds so that neither one feels like they’re being sneaky.

An FWB situation shouldn’t be something either person is ashamed of; otherwise, it’s not fair for anyone involved.

If your boyfriend or girlfriend doesn’t approve, take a step back and figure out why that is before diving into anything further.

11. What do you want out of our relationship? This is probably one of the most important questions that you can ask an FWB.

Just because someone wants to be your friend doesn’t mean that they want to engage in a physical relationship, nor does it mean that they want exactly what you are thinking.

Make sure that you’re clear on what everyone’s expectations are so neither of you feels left out or deceived in any way.

To avoid confusion and hurt feelings, use ‘I’ statements, instead of ‘you’ statements as much as possible when voicing your feelings.

This will help make everything much less personal and allow each person to have their own unique set of expectations without there being any unnecessary finger-pointing involved (which can be common when emotions get heated!).

12. What are we going to do if one of us wants more? I know that sometimes we get so caught up in an FWB situation that we forget what is really going on and each person has their own wants and needs outside of what they are doing.

Make sure you have a plan in place because once feelings start coming into play, it can be tricky! If either one of you is getting attached, figure out how you want to handle it so both parties can feel good about what’s happening.

Just because you’re feeling something for someone doesn’t mean that they are necessarily feeling anything for you, so don’t assume anything until all cards are on the table.

Also read: 75 Questions for friends with benefits

13. Do we make a good FWBR couple? Having an open line of communication is so important in any type of relationship, but even more so if you are engaging in an FWB situation.

If something feels off or weird between you and your partner, talk about it right away! Don’t keep something simmering until it becomes a huge problem that you can’t ignore any longer.

Be honest and be direct when speaking your mind—you’re both adults who should be able to handle whatever happens.

Even if things don’t pan out after being FWB for a while, at least you will know where both of you stand and can move on from there without having any negative feelings lingering around because things didn’t work out exactly as expected.

14. What happens if we break up? If you’re currently in a monogamous relationship but engaging in an FWB situation on top of that, then be prepared for how you are going to handle things if one of you decides they want more.

The only way an FWB situation can work is if both parties are comfortable and happy with what is going on.

So make sure that you talk about your expectations as well as what could potentially happen down the road if either party wants something different. It’s always better to be safe than sorry when it comes to relationships.

15. How do you define just s#x? This is something that both parties involved should have a clear idea of before entering into an FWB situation so that way everyone can be on the same page about what is going on between them.

Be specific about what your expectations are and try not to leave anything out because otherwise, things might get awkward or unfulfilling later down the road.

16. Are we both in agreement about our need/desire for discretion? You don’t want anyone knowing about your FWB situation—or at least as few people as possible.

Not only is it just not good to talk about the fling, it’s also not wise because someone may try and make things difficult or awkward for you down the road if they find out.

Just because you’re not exclusive doesn’t mean that others won’t take issue with what you are doing, so do whatever it takes to keep things quiet and discreet before saying anything to other people.

17. What is going on between us emotionally? Don’t jump into an FWB situation just because you have a desire for a casual fling—make sure that there is something more involved than just physical needs being met by being able to engage in a romantic activity together.

18. How will we handle possible rejection by a prospective FWBR partner of either one of us?

Before you get involved in an FWB situation, you should have a clear idea of how you are going to handle being rejected for a physical relationship if that’s what is happening between you and your prospective partner.

Do whatever it takes to keep from having hurt feelings from getting involved, but also don’t be surprised if someone turns down your advances.

It happens all of the time, so just do your best to be prepared and get on with your life because there are plenty more fish in the sea waiting for their chance at some casual fun.

19. Are we ready to engage in a FWB situation? Make sure that you and your prospective FWBR partner are both on board with getting involved in a no-strings-attached intimate arrangement.

You should be completely honest about what you want and need before pursuing an FWB situation because you don’t want to hurt anyone’s feelings or end up getting yourself into something you don’t really care for or want.

If either one of you isn’t interested, then there is no reason why you should pursue an FWB situation—just say no thanks and keep looking for someone who does want what you have to offer.

20. Have we agreed upon who will bring things up first if we wish/need to move our friendship forward into more than just physical intimacy?

You don’t want either party to be caught off guard when wanting or needing something that is different from what they are getting in their current FWB situation.

Do whatever it takes to make sure that you have a plan for whatever happens between you two so that way both of you can be comfortable and happy with what is going on between each other.

21. What are all of my options concerning friends with benefits relationships?

Don’t jump headfirst into having a FWBR situation without considering your other options—after all, being single does mean that there are plenty of men and women out there looking for no-strings-attached s#x partners on a regular basis.

Related: 100+ Questions to ask your friends with benefits

Fun questions to ask your friends with benefits

fun questions to ask your friends with benefits 50+ Questions to ask your FWB

Here is a list of fun questions to ask your FWB

1. If you could put one s#x toy into our bed for us to play with, what would it be? 

2. What is your most erotic fantasy? 

3. Do you have any fetishes that I don’t know about? 

4. How do you feel about dating couples or men and women at once? 

5. Have you ever hooked up with someone from a dating app before or after having a FWB situation? If so, which one(s)? 

6. Would it bother you if your FWBR partner went on a date with someone else if he/she asked for your permission first? Would you say yes or no, and why?

7. What was your most memorable s#xual experience? 

8. What was your first s#xual experience like? 

9. Have you ever engaged in an orgy before? How many people were involved and what made it so memorable for you? 

10. If we were alone on a deserted island and could have s#x whenever we wanted, how would you use me s#xually over the course of a week while on that island?

The world is your oyster my friend! This is a no-holds-barred question that will give you tons of insight into what your FWBR partner likes when it comes to having fun in bed together!

Dirty questions to ask your fwb

dirty questions to ask your friends with benefits 50+ Questions to ask your FWB

Here is a list of dirty questions to ask your friends with benefits:

1. Would you ever p## on me if I begged you to?

2. Would you ever engage in a threesome, foursome, or more?

If so, would you want it with one guy and two girls or two guys and one girl or one guy and two girls? What’s your reasoning behind wanting that kind of group s#x experience? 

3. Do you have any experience being dominant during s#x or in a s#xual relationship before? If so, how did it make you feel while going through it?

4. Have you ever been submissive during s#x or in a s#xual relationship before, and if so what did that involve for your partner(s)?

5. Have you ever had a physical fling in public?

6. Would you make out with me in public?

7. How much do you like sw#ngers party?

8. What is your favorite position/s?

9. Where do you like to make out with me every time?

10. Do you prefer people watching when making out or not being watched at all during your s#xual experiences?

11. Have you ever had a threesome before (with two of more partners)? 

12. How would your ideal threesome go down?

13. Do you want one guy and two girls as part of your threesome or vice versa?

14. Would you rather watch someone else have s#x instead of participating yourself, why or why not?

15. Would you be okay with me participating in a foursome if I asked permission first before doing so?

16. Are there any fetishes that are completely off limits to me if we are into each other s#xually outside of our FWB situation together?

17. Which three fetishes would most turn me on to explore with you s#xually during our FWB situation together without question?

18. Who usually initiates getting kinky s#xually between us both most often during an FWB situation together?

19. When was your last s#xual encounter with someone outside of our FWB situation together and how long ago was it?

20. When was your first s#xual encounter outside of our FWB situation together? 

Related: Your complete guide to friends with benefits


  • Naveen B

    Experienced Psychology and philosophy Writer, self-help and relationship Coach and thought influencer. He has 7 years of experience in Personal development industry. His expertise as a self-help and relationship Coach has been highlighted through his articles in medium and substack to name a few. To be updated with his latest work, connect with him by following his social media accounts.

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Experienced Psychology and philosophy Writer, self-help and relationship Coach and thought influencer. He has 7 years of experience in Personal development industry. His expertise as a self-help and relationship Coach has been highlighted through his articles in medium and substack to name a few. To be updated with his latest work, connect with him by following his social media accounts.

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