Would You Still Date Them If…? 100 Brutally Honest Dating Questions

Everyone says they have deal-breakers. Then they meet someone extremely attractive and suddenly the constitution is open to amendments.

So here is a better test. Do not ask yourself whether something is theoretically a red flag. Ask whether you would actually keep dating a person you liked if you discovered it tomorrow.

No correct answers. No compatibility score at the end. No internet stranger telling you that preferring separate bank accounts means you have an avoidant attachment style. Just one question, repeated 100 different ways: would you still date them if?

Do this alone, with a date, or with a partner. The disagreements are more interesting than the agreements.

Money

1. Would you still date them if they had $50,000 in debt?
2. If they earned half what you earn?
3. If they earned five times what you earn?
4. If they never saved money?
5. If they tracked every dollar they spent?
6. If they regularly gave money to their parents?
7. If they wanted completely separate finances after marriage?
8. If they expected one person to pay for almost every date?
9. If they loved expensive things but had an average income?
10. If they refused to tell you how much debt they had until the relationship became serious?

Money questions rarely stay about money for long. They turn into fairness, security, ambition, independence and what each person thinks a partnership owes the other.

Exes

11. Would you still date them if their best friend was an ex?
12. If they spoke to an ex every day?
13. If they still had photos with an ex all over Instagram?
14. If they had cheated once in a previous relationship?
15. If they said every one of their exes was "crazy"?
16. If an ex still called them for emotional support?
17. If they wanted to go to an ex's wedding?
18. If they compared you favourably with an ex?
19. If they compared you unfavourably with one?
20. If they refused to discuss previous relationships at all?

There is a difference between having a past and still living inside it. Where you draw that line is the useful part.

Read also: 75 Questions to Ask Before Marriage: Money, Kids, Sex & Deal-Breakers

Phone, privacy and social media

21. Would you still date them if they wanted your phone password?
22. If they would not give you theirs?
23. If their phone was always face-down around you?
24. If they posted almost every detail of the relationship online?
25. If they never posted you at all?
26. If they followed hundreds of attractive strangers?
27. If they regularly liked an ex's photos?
28. If they read your messages without permission once?
29. If they shared screenshots of your arguments with friends?
30. If they expected you to share your location whenever you went out?

A useful distinction here is privacy versus secrecy. Most people want some privacy. Far fewer people are comfortable feeling deliberately kept in the dark.

Sex and attraction

31. Would you still date them if their sex drive was much higher than yours?
32. Much lower?
33. If they almost never initiated sex?
34. If physical affection mattered enormously to them?
35. If they disliked kissing in public?
36. If they watched pornography?
37. If they had a sexual preference you did not share?
38. If they wanted to keep their sexual history private?
39. If your sexual chemistry was good but not extraordinary?
40. If you were deeply compatible everywhere except in bed?

This section tends to expose one of dating's stranger assumptions: that sexual compatibility should somehow arrive fully formed and require no conversation. Sometimes it does. Often it does not.

Marriage and commitment

41. Would you still date them if they never wanted to marry?
42. If they wanted to marry within two years?
43. If they wanted a huge wedding and you hated the idea?
44. If they believed divorce should almost never be an option?
45. If they wanted a prenup?
46. If they refused to sign one?
47. If they wanted to live together before engagement?
48. If they refused to live together before marriage?
49. If they had already been married twice?
50. If they could not tell you whether they saw a future with you after a year?

Some of these are preferences. Some are genuine incompatibilities. A person who wants marriage and a person who absolutely does not are not going to compromise their way into half a marriage.

Children

51. Would you still date them if they definitely wanted children?
52. If they definitely did not?
53. If they already had children?
54. If they wanted four children and you wanted one?
55. If they believed one parent should stay home?
56. If they wanted to raise children in a religion you do not practise?
57. If they would consider adoption but not fertility treatment?
58. If they expected grandparents to be heavily involved?
59. If they disagreed with you about discipline?
60. If they said, "I don't know if I want kids, maybe someday," at 35?

There are relationship disagreements where a middle ground exists. Children are one of the clearest examples where sometimes it simply does not.

Friends and nightlife

61. Would you still date them if they went out drinking every weekend?
62. If they almost never wanted to go out?
63. If most of their closest friends were single?
64. If they disliked your best friend?
65. If your best friend disliked them?
66. If they wanted several nights a week with friends without you?
67. If they regularly stayed out until 3 a.m.?
68. If they had a close friend who openly flirted with them?
69. If they refused to attend social events with you?
70. If they expected to be invited everywhere you went?

The interesting question is usually not "how social are you?" It is "how separate are we allowed to be?"

Read also: 130 Would You Rather Questions for Couples: Funny, Flirty & Deep

Lifestyle

71. Would you still date them if they were extremely messy?
72. If they were obsessively tidy?
73. If they smoked?
74. If they drank no alcohol at all?
75. If they wanted to live in another country?
76. If they never wanted to leave their hometown?
77. If they wanted pets and you did not?
78. If they worked 70 hours a week?
79. If they wanted to retire early and live very simply?
80. If their ideal weekend looked completely different from yours?

People spend a lot of time asking whether someone is interesting. Long relationships eventually ask a less glamorous question: do we actually enjoy living the same kind of Tuesday? That is why compatibility is often easier to see in ordinary routines than in exceptional dates.

Jealousy and trust

81. Would you still date them if they were uncomfortable with you having close friends of another gender?
82. If they got jealous easily but admitted it?
83. If they insisted jealousy meant they cared?
84. If they had previously been unfaithful but told you before you asked?
85. If they had been cheated on and now found trust difficult?
86. If they wanted to know who you were texting?
87. If they became uncomfortable when you travelled without them?
88. If they flirted naturally with everyone?
89. If they accused you of flirting when you thought you were simply being friendly?
90. If they trusted you completely but wanted a lot more independence than you did?

Jealousy questions are useful because people often agree that "trust matters" while defining trust in completely different ways. One person hears trust and thinks freedom. Another hears trust and thinks transparency. Neither definition stays theoretical once you start dating.

The uncomfortable ten

91. Would you still date them if they disagreed strongly with your politics?
92. If they practised a religion you did not believe in?
93. If their family openly disliked you?
94. If they did not get along with your family?
95. If they had a history of addiction but had been in recovery for years?
96. If they had a serious chronic illness that changed the life you imagined together?
97. If they wanted to care for an ageing parent in your home?
98. If their biggest life goal required you to move?
99. If they told you there was one part of their personality they had no intention of changing?
100. If they were exactly the person they are today ten years from now?

Number 100 is the one I would keep. Dating makes it very easy to fall in love with potential. Someone will become more ambitious. Less jealous. Better with money. More affectionate. Ready for children. Interested in travelling. Kinder to your friends. Maybe. But if the relationship only works after three significant personality renovations, you are not really deciding whether you want the person in front of you. You are deciding whether you want their proposed future version.

Now find your actual deal-breakers

Do not count how many times you answered yes. Instead, go back through the list and mark every question where your answer was an immediate "absolutely not." Those are your boundaries.

Now make a second mark beside every question where you suspect the person you are dating would answer differently. That list is more interesting, because compatibility does not mean agreeing about everything. It means knowing which disagreements are negotiable and which ones eventually force one person to live a life they never wanted.

For a more serious version of that exercise, our 75 questions to ask before marriage cover money, children, sex, family, career and deal-breakers in more depth, and our guide to how to know if you are compatible with someone looks at the bigger picture. And if 100 uncomfortable questions are enough for one evening, the would you rather questions for couples are considerably less likely to end with someone reconsidering where they want to raise children.

SoulMatcher's compatibility profile approaches the same problem from another direction: not "do we agree on everything?" but "where are our differences likely to matter?" That is usually a much more useful question.