Before you hop into bed with a new partner, it’s important to be prepared. Knowing what you’re getting into can help make your friends-with-benefits relationship more successful and less stressful.
Here are some questions worth asking yourself and potential questions to ask your friends with benefits
Do I have time for a fling?
Can I handle a casual s#xual relationship?
Am I emotionally available for a casual fling?
Is there anything that would cause me to end our friendship if things go south in bed?
Think about it — would you want to lose someone over something as silly as s#x, or even just getting along? If so, you might need to reevaluate whether a FWB situation is right for you at all.
But if none of these sound like big issues to you — great! You’ve checked all your boxes and now know whether or not becoming an FWB could work out in your favor.
But take note: This doesn’t mean you should dive right into having s#x with one another. You don’t want to ruin a good thing (and potentially bad friendships) by moving too fast.
100+ Questions to ask your friends with benefits
Here is a list of questions to ask your FWB:
1. Are you comfortable having a no-strings-attached physical relationship?
2. How often do you want to have s#x (how often are you in the mood)?
3. What are your long-term goals for our s#xual relationship?
(ex: Casual s#x is great, but I’d love to see what it would be like in a serious dating/s#xual monogamous type of way or, I really just want something casual where we can enjoy each other’s bodies without any long-term strings attached).
4. Do you want me to be s#xually faithful to only you? Or do you just want me around for your pleasure regardless of how many other people I may or may not be sleeping with outside of our FWB arrangement at that time?
5. How soon would you like us to have s#x?
6. Do you use protection (both s#xually transmitted infections and pregnancy prevention)?
7. If we’ve agreed that we are just s#xual partners, what happens if a romantic connection begins between us?
8. How long do you want our FWB arrangement to last?
9. What do you want to say when people ask how we met (and why are we not a couple)?
10. What if one of us meets someone else, is it over between us?
11. What should I do about having a physical relationship with others?
12. Do you want me there when you sleep with other people (should I just let you be or watch, etc.)?
13. Do you have STIs? If so, how long after your last s#xual encounter did you wait before we slept together again?
14. What kind of birth control will you use if we decide to have s#x?
15. If I have to cancel on you last minute, should I offer an excuse or just say I can’t make it?
16. How do you feel about s#x toys and p#rn?
17. Do you prefer receiving oral or performing oral during s#x?
18. What kinds of positions/positions do you like in bed?
19. Is there anything else that we need to discuss before we sleep together again (use your judgment)?
20. What are some of your turn-offs in a s#xual partner, if any?
21. What do you enjoy doing/talking about/listening to before, during, and after s#x?
22. Would you ever consider taking a break from our FWB arrangement if we found out we had more in common than just s#x (ex: going on dates, hanging out with each other outside of our s#xual encounters)?
23. How often do you masturbate outside of our s#xual encounters?
24. Are there any red flags that should make me immediately stop all communication and contact with you for my own protection (in case I decide to pursue dating/getting into a serious monogamous relationship with you in the future)?
25. If someone else asked me out on a date, would that be ok?
26. Are you willing to wear a condom if we decide to have s#x?
27. Do you ever make any type of self-improvement attempts in your life? (ex: body-building, going on healthy diets, quitting smoking, practicing relaxation techniques, etc.) ?
28. How often do you go on dates and how would you rate your dating skills? (Not everyone has good dating skills; it doesn’t mean they don’t like/love people).
29. Have you ever had an experience where someone lied about their age or career level just so they could impress/attract others? And if so, what happened as a result of that lie being found out later down the road?
30. Have you ever done anything illegal (in your state or out of state) and what was that experience like?
Questions to ask a friend with benefits
Here is a list of questions to ask a friend with benefits
31. Have you ever been s#xually abused in any way (as a child, teenager, adult)?
32. Are there any types of men/women you have previously not gotten along with very well in dating situations?
33. Would it be ok if I told my friends about our FWB arrangement? And do you have any of your own guidelines on who you would feel comfortable letting know about us having physical intimacy outside of an official relationship?
34. What kind of jobs do you have (not including entrepreneurs and/or people who don’t have full-time jobs)?
35. How many ho#kup partners have you had?
Also read: 50+ Questions to ask your FWB
36. How often do you exercise?
37. Do you generally have a positive outlook on life or are you always the negative type of person? And what would be your general reaction if something bad happens in my life that I tell you about?
38. Is there anything I can do for you before, during, or after s#x that could potentially make your experience more enjoyable for you?
39. Have you ever used drugs (prescription, illegal, or anything in between) while engaging in s#xual activity? If so, how did it affect your overall s#xual experience and would you recommend doing it again in a similar situation?
40. What makes a good first date for you (if anything at all)? And what about the first dates that do not work for you? What do you dislike most about first dates?
41. Have you ever had a s#xual experience that made you feel so good that you wish someone would film it and put it online for everyone else to see? How did that make you feel afterward?
42. Have you ever considered, or do consider yourself today, as a feminist? What does that mean to you exactly? Do you have any current feminist views on relationships with men versus relationships with women in general?
43. Are there any reasons why we should not continue having s#x outside of an official monogamous committed relationship and what would those reasons be if they existed?
44. What is your definition of love? And how would you describe your feelings on marriage and/or a committed long-term monogamous relationship?
45. What are your thoughts on PDA (Public Displays of Affection) and S&M (Safe, Sane, & Consensual Spanking/D/s or Domination/submission)?
46. Have you ever been responsible for bringing two people together who became a couple in any way (not just s#x)? If so, what were their names and how did you meet them? How was that experience for you overall?
47. Have you ever had any s#xual experiences involving animals or other non-human objects?
48. What are your thoughts on s#xting and or sending naughty pictures of yourself?
49. How long did it take you to get ready for your last date and what did you do? (Ask them when they had s#x before a date, not after, if that’s important for a reason).
50. Are there any types of foreplay that turn you on and off (e.g., kissing different parts of your body, touching on certain areas vs. Others; no face kissing)?
Also read: 150+ Friends with benefits questions
Friends with benefits questions to ask
51. What types of food do you like most/least? And have you ever had a bad first-date experience because of food allergies or dislikes? What about good first-date experiences based around eating good food together?
52. What have you been up to lately, and what are your plans for (the week or month of) our first date?
53. What would be your ideal place for a first date (if not somewhere we could go right now)?
54. What kind of things/activities do you enjoy doing in your free time? And how often do you get to do those things on a regular basis since work takes up so much of it?
55. If we were somehow able to get away from everyone else on a tropical island somewhere, what activities would we most likely find ourselves doing together and why?
56. What do you consider to be your best physical attribute(s)? How about your most attractive characteristic(s) and why?
57. What qualities do you appreciate most in another person? And what are some of your favorite qualities about yourself?
58. Do you have any pets and if so, what kind and how many do you have (if any)? How long have they been part of your family?
59. Have you ever had a one-night stand or casual s#x partner before and how was that experience for you? Would you repeat it again given another chance knowing what you know now? If not, why not (definitely/probably/maybe not)?
60. What are your thoughts on long-distance relationships?
Also read: 15 Pros and Cons of Friends With Benefits
61. What about jealousy in a relationship and how do you handle it? If you’ve been cheated on, would that break up a relationship?
62. How well do you get along with your parents, if at all? And how often do you talk to them, either by phone or in-person (not including social media updates)?
63. Do people consider you an honest person and if not, why not?
64. Have you ever had any past romantic partners who were in a relationship with someone else, or cheated on them (either prior to or during your time together)? And if so, how did that experience make you feel?
65. What would be your ideal wedding day and location like? Do you have any children? If not, how many would you like to have in total and how far apart should they be from each other in age?
66. Do you believe marriage is forever, until someone cheats/dies, etc., or are you okay with divorce when one spouse no longer feels love for another? Why?
67. How did you decide that you wanted to be an/the (fill in profession)? And why did you choose a career in that field?
68. Are there any professions that disgust you, or which most people are way too obsessed over? If so, what and why?
69. Where do you see yourself living five years from now (or whenever our time together ends)? What would your life look like five years from now if things were exactly as they are today?
70. Have you ever left a long-term job/relationship/marriage or moved away from home just because it wasn’t right for you anymore or it wasn’t working out?
Also read: Can fwb turn into a relationship?
Questions to ask a potential fwb
71. If you’re an introvert or an extrovert, do you prefer spending time alone or being around other people? And how long is your ideal alone time in between doing other things?
72. What are some of your favorite aspects of living in (city/state) and why? If you had to choose a different place to live in, where would it be and why would you move there?
73. What would your ideal weekend be like?
74. What is one thing you’ve always wanted to do but haven’t yet?
75. How often are you on social media (Twitter, Facebook, Instagram), and how much time do you spend online on a typical day? Are there any websites or books/blogs that you regularly check out besides social media?
76. If money was no object, what car would you drive and why?
77. Have you ever done drugs or drunk alcohol before and if so, how often did you use them and why did/do you do it?
78. What is your favorite book, magazine, or website that you go back to reading or visiting on a regular basis?
79. Do you have any pets (dog, cat, fish, etc.), and if so how many and what are their names?
80. Do you like animals in general (pets or wild animals) and if so which are your favorites?
Also read: What to do when friends with benefits ends?
81. How long does it take for you to get ready in the morning/get ready for bed at night?
82. What is one thing that makes you feel most attractive about yourself? And why do others find it attractive too?
83. What is one thing you wish you could change about yourself? Why? And have you tried doing that but failed, or do you plan on trying it again in the future?
84. What do you like least about living in (city/state)?
85. If there was something I could magically change about my appearance for both of us, what would it be and why?
86. What are some things that annoy or frustrate you and why?
87. How many hours of sleep do you get every night and what times do your wake up naturally (without an alarm clock)?
88. What are some of your favorite websites and blogs that you visit on a regular basis?
89. What is one thing you can’t live without for at least a month, or one week if it’s really important? Why do you need it and what would happen if you couldn’t have it anymore?
90. Have you ever been hurt physically or emotionally in a serious relationship (long-term boyfriend/girlfriend, husband/wife, etc.)?
If so, how did that happen and what did it feel like at the time? How long did it take for your heart/body to fully heal and how long were they actually gone from your life (or do they still linger)?
91. What was your last major fight about and why did it happen? What did you do afterward?
92. What’s one thing that makes you really happy right now in your life (even if it’s not directly related to our relationship)? Why is it making you so happy?
93. How often do you read a book or a magazine (regularly/sometimes/rarely) and what kind of books or magazines are they (or what genre are they from memoir, mystery, science fiction, etc.)?
94. If we were in an accident and lost all of our possessions except for two things, what would those two things be and why would we want them with us during such an experience?
95. What is one thing that you want to learn in life and why?
96. If you had enough money, how would you change your career path/job?
97. How often do you volunteer for charities or donate money or time to others in need? Why do you choose those things over other options (for example, more material possessions)?
98. What is one thing that makes you cry easily and why does it happen so quickly (is it an event, a feeling, a memory)?
99. If we were stranded on a deserted island together and only had books available for entertainment for the rest of our lives, what books would you bring along with us and why?
100. Have you ever been in love and what did it feel like?
101. What was your first impression of me when we first met? Why did you think that way?
102. If our children could be anything or do anything in life, what would you want them to be or do?
103. How often do you have nightmares and if so, can you remember any specific ones from when we were apart?
104. Have you ever experienced a moment where something or someone turned your life around forever (positively or negatively)? What happened and how did it affect your outlook on life for better or worse?
105. What is your most embarrassing moment? How did it happen and why were you embarrassed?
106. If we had a house fire, what three things would you save first (you can only choose three, no matter how much money or time you have)? Why would those be your top choices?
107. What is one thing that you wish someone had told you when you were a teenager (no matter how embarrassing or inappropriate it might have been at the time)?
108. What do I mean to you and why do I mean so much. If so?
109. What do you like most about me and why? What makes me special?
110. If we could go anywhere in the world together (as a vacation or for any other reason), where would you take me and why would it be your first choice?
111. Are there any hobbies or activities that you want to explore together and why? What are they and what do they involve (the more detailed, specific information you can give, the better)?
112. How much money would you need to earn a year for it to be enough for us (including food/housing/bills/fun money) so we could live comfortably without having to worry about anything else?
113. If someone asked you in general if life was worth living, what would your answer be? Why would you choose that option over others?
114. How would our kids be different from us when it comes to personality and interests and why would those things happen (in other words, how does nature vs nurture play into their character)?
Questions to ask before becoming friends with benefits
1. Are my needs being met by him/her?
2. Do I genuinely care about him/her as a person?
3. Can we maintain our friendship outside of our s#x life?
4. Is a friends with benefits relationship right for me?
5. What are the steps for starting up Friends With Benefits Relationship?
6. How to know if you are in a FWBR?
7. Is FWBR better than normal relationships?
8. How do you start and end FWBR?
9. Why don’t friends with benefits relationships last?
10. How to know if you are in a friend zone?
11. Do I have a BFFL or FWB?
12. How to choose your FWB partner?
13. How can you make sure that you are safe from STDs?
14. How do I know if I want something serious with my friend-with-benefits partner?
15. What Is Friends With Benefits Relationship?
16. Why do Some People Say FWB Relationship is Not For Them?
17. What are the Pros and Cons of Friends With Benefits Relationship?