175 This or That Questions for Your Boyfriend: Cute, Funny, Flirty, and Deep

You do not need a serious topic to have a memorable conversation with your boyfriend. Sometimes, choosing between two simple options can reveal a funny habit, an unexpected preference, or a side of him you have not seen before.

These this-or-that questions for your boyfriend range from cute and playful to romantic and thoughtful. Ask them during a date night, send a few over text, or use them to pass the time on a road trip.

How to Play This or That With Your Boyfriend

The game is simple: read two options and ask your boyfriend to choose one. There are no points to earn and no correct answers.

• Take turns asking the questions.
• Answer at the same time to see whether your choices match.
• Guess each other’s answers before revealing them.
• Ask why when a choice surprises you.
• Let either person skip a question that feels uncomfortable.

Matching answers can be fun, but different choices often lead to better conversations. Treat the questions as conversation starters rather than a test of how compatible you are.

Cute This or That Questions for Your Boyfriend

Begin with affectionate questions about the small gestures and everyday moments that make a relationship feel special.

1. A good-morning text or a good-night call?
2. Holding hands on a walk or cuddling on the couch?
3. A forehead kiss or a cheek kiss?
4. A silly drawing or a custom phone wallpaper?
5. Sharing a hoodie or sharing a blanket?
6. A cute nickname or a private inside joke?
7. A candid photo together or a carefully posed one?
8. Remembering your usual coffee order or remembering a tiny detail you once mentioned?
9. Celebrating a small win or cheering you up after a rough day?
10. A funny voice note or a sweet selfie?
11. Doing an errand for you or making you a warm drink?
12. Sitting together in comfortable silence or talking until midnight?
13. A lazy Sunday morning or an unplanned coffee break together?
14. Sharing an umbrella or offering you a jacket?
15. Letting you choose the movie or letting you pick the snacks?

Funny This or That Questions for Your Boyfriend

These ridiculous choices are designed to create laughter, playful arguments, and plenty of strange mental images.

16. A dance contest in the kitchen or karaoke in the car?
17. Only being able to whisper or only being able to sing?
18. Getting hiccups on a date or sneezing during a serious conversation?
19. Matching pajamas or matching Halloween costumes?
20. Stealing all the fries or stealing all the blankets?
21. Communicating only through movie quotes or only through memes?
22. Having a robotic laugh or a cartoon-character sneeze?
23. Being chased by one giant duck or ten tiny horses?
24. Always arriving 10 minutes early or always arriving 20 minutes late?
25. Getting matching bad haircuts or wearing matching terrible outfits?
26. Entering a haunted house with no lights or an escape room with no clues?
27. Wearing socks with sandals everywhere or formal clothes to buy groceries?
28. Accidentally sending a flirty text to your mom or a heart emoji to your boss?
29. Eating dessert for breakfast or breakfast for dinner?
30. Having a pet that repeats your arguments or one that narrates your kisses?
31. Tripping in front of a crowd or waving back at someone who was not waving at you?
32. Closing your eyes in every photo or always noticing food in your teeth afterward?
33. Taking a road trip with nonstop off-key singing or with no music at all?
34. Temporarily losing one eyebrow or all your eyelashes?
35. Being known for dramatic sneezes or incredibly loud stomach growls?

Flirty This or That Questions for Your Boyfriend

Use these questions when you want the conversation to feel playful, confident, and a little more romantic.

36. A slow kiss or a quick stolen kiss?
37. Playful teasing or bold compliments?
38. Making the first move or being surprised by it?
39. Flirty eye contact across the room or a secret text from beside you?
40. Dressing up for a date or looking attractive in your coziest clothes?
41. Accidentally-on-purpose touching hands or standing a little too close?
42. A whispered line or a subtle hand squeeze?
43. Building anticipation or following a spontaneous spark?
44. Pulling him closer or letting him pull you closer?
45. A playful wink or a mischievous smile?
46. Butterflies before a date or missing each other immediately afterward?
47. A playful dare or a confident invitation?
48. A private joke during dinner or a flirty challenge during a game?
49. Flirting in person or flirting over text?
50. Ending a date with a kiss or with a hug that lasts too long?

Romantic This or That Questions for Your Boyfriend

Romance can mean heartfelt words, meaningful traditions, or thoughtful gestures. These questions explore what makes each of you feel loved.

51. A handwritten love letter or a heartfelt voice message?
52. A private rooftop moment or a cozy evening by the fireplace?
53. Recreating your first date or planning a completely new one?
54. Flowers or a meaningful keepsake?
55. Slow dancing at home or stargazing outside?
56. A memory box or a scrapbook?
57. One grand romantic surprise or small loving gestures every day?
58. Saying “I love you” often or showing it through actions?
59. A weekend getaway or a cozy staycation?
60. A special song or a special place that belongs to the two of you?
61. Celebrating every small milestone or only the major anniversaries?
62. A romantic toast or a private promise?
63. Reading your earliest messages or watching old videos together?
64. Starting a new couple tradition or continuing an old favorite?
65. Writing down your love story or telling it to each other from memory?

Getting-to-Know-You Questions for Your Boyfriend

Even after spending plenty of time together, you may still be surprised by how your boyfriend approaches decisions, habits, and everyday situations.

66. Being an early bird or a night owl?
67. Following rules exactly or improvising as you go?
68. Recharging alone or recharging around other people?
69. Making decisions with logic or trusting your intuition?
70. Taking the lead or supporting someone else’s plan?
71. Thinking out loud or sorting through thoughts quietly?
72. Multitasking or focusing on one task at a time?
73. Competing for fun or cooperating toward a shared goal?
74. Keeping a perfectly tidy workspace or working within a creative mess?
75. Learning by doing or reading the instructions first?
76. Taking plenty of photos or staying fully in the moment?
77. Trying a new dish or ordering a familiar favorite?
78. Using a detailed calendar or relying on memory?
79. Keeping sentimental objects or clearing out clutter regularly?
80. Asking for directions or figuring out the route alone?
81. Fixing something yourself or calling an expert?
82. Choosing quickly or comparing every option?
83. Working with background noise or needing complete quiet?
84. Spending free time on one favorite hobby or rotating among several?
85. Sharing a story in every detail or getting straight to the point?

Deep This or That Questions for Your Boyfriend

These choices explore values, priorities, and the way your boyfriend sees life. Give each other time to think instead of rushing through them.

86. Being deeply understood or widely admired?
87. Having stability or having freedom?
88. Choosing happiness or choosing success?
89. Remembering every lesson or letting the past go?
90. Knowing your future or changing one part of your past?
91. Hearing a painful truth or living with peaceful uncertainty?
92. Following your passion or choosing financial security?
93. Being remembered for kindness or for achievement?
94. Having more time or having more money?
95. Following firm principles or adapting to the circumstances?
96. Feeling a strong sense of belonging or maintaining complete independence?
97. Taking a meaningful risk or wondering what might have happened?
98. Protecting your time or always making room to help others?
99. Learning through failure or avoiding the mistake entirely?
100. Always speaking your mind or preserving harmony?
101. Giving someone a second chance or making a clean break?
102. Having a few extremely close relationships or a wide social circle?
103. Living with a clear purpose or living for adventure?
104. Seeking justice or extending mercy?
105. Leaving a lasting legacy or being fully present in your lifetime?

Relationship This or That Questions

These questions focus on communication, boundaries, responsibilities, and the ways two people support each other in a relationship.

106. Resolving a disagreement right away or cooling down before talking?
107. Frequent short texts or one long evening call?
108. Talking through stress or distracting yourselves for a while?
109. Sharing most hobbies or maintaining separate interests?
110. Doing everyday tasks together or setting aside dedicated date time?
111. Apologizing with words or making amends through actions?
112. Celebrating an anniversary privately or with friends and family?
113. Dividing chores by preference or rotating them equally?
114. Combining most finances or keeping personal spending money separate?
115. Sharing nearly everything or preserving some personal privacy?
116. Showing affection openly or keeping romantic moments private?
117. Having a simple date every week or a bigger outing once a month?
118. Usually agreeing or enjoying respectful debates?
119. Receiving a surprise gift or being asked exactly what you want?
120. Checking in often or trusting each other to ask for space?
121. Solving problems together or dividing responsibilities?
122. Discussing every decision together or only the major ones?
123. Taking turns planning dates or planning every date together?
124. Receiving verbal reassurance or practical help?
125. Pursuing shared goals or supporting separate individual goals?

Future-Focused This or That Questions

You do not need to make firm plans based on these answers. Use the questions to compare the lifestyles, priorities, and possibilities each of you imagines.

126. Living in a busy city or the quiet countryside?
127. Renting for flexibility or owning for stability?
128. Faster career growth or more personal time?
129. Living near family or moving somewhere completely new?
130. Several short trips or one long vacation each year?
131. A smaller home in a great location or a larger home farther away?
132. Working remotely or going to a regular workplace?
133. Saving aggressively now or spending more on meaningful experiences?
134. Settling in one place early or exploring for several more years?
135. Building one long-term career or reinventing yourself along the way?
136. Building a future with pets or keeping the household pet-free?
137. Retiring early or working longer at something you enjoy?
138. Following a detailed five-year plan or reviewing life one year at a time?
139. Living somewhere warm year-round or somewhere with four distinct seasons?
140. A busy household with frequent guests or a quiet home with fewer visitors?

Date Night and Adventure Questions

These choices can double as date inspiration. Save the answers you both like and turn them into plans for a future weekend.

141. Dinner at a restaurant or a picnic outside?
142. A live concert or a sporting event?
143. A beach day or a mountain hike?
144. A long road trip or a quick flight?
145. Visiting a museum or spending the day at an amusement park?
146. Taking a cooking class or a pottery class?
147. Camping under the stars or staying in a comfortable hotel?
148. A sunrise hike or a late-night drive?
149. Browsing a bookstore or relaxing in a café?
150. A comedy show or a theater performance?
151. Bowling or miniature golf?
152. Exploring a farmers market or attending a food festival?
153. A long bike ride or a relaxing boat ride?
154. Watching a movie at the theater or setting up an outdoor screening?
155. Visiting an arcade or joining a trivia night?
156. Exploring a nearby town by train or touring your own city like visitors?
157. A dance lesson or a paint night?
158. Visiting an aquarium or exploring a zoo?
159. Volunteering at a community event or competing in a game tournament?
160. Choosing the next date with a coin flip or drawing an idea from a jar?

Rapid-Fire This or That Questions to Text Your Boyfriend

These short choices are easy to send one at a time or use in a fast round. Answer immediately, then return to any choices that deserve an explanation.

161. Coffee or tea?
162. Dogs or cats?
163. Music or podcasts?
164. Sweet snacks or salty snacks?
165. Sneakers or boots?
166. Spring or fall?
167. A laptop or a tablet?
168. Super speed or invisibility?
169. Rain or snow?
170. A paperback or an audiobook?
171. A window seat or an aisle seat?
172. Hot sauce or ketchup?
173. Board games or video games?
174. Pizza or tacos?
175. Exploring the ocean or exploring space?

You do not have to ask all 175 questions in one sitting. Choose a section that fits the mood, mix light questions with more thoughtful ones, and pause whenever an answer leads to a conversation of its own. The reasons behind the choices are often more revealing than the choices themselves.