When chatting with older women on dating apps like Bumble, Tinder, or Hinge, asking flirty funny questions can be a great way to break the ice.
It can also be a good way to create a deeper connection and get to know each other better while having fun.
Today we will share with you a huge list of funny, interesting, and unique flirty questions that are sure to spark some intriguing conversations between the two of you.
Whether it is about her hobbies or past dating experiences, these flirty questions will take your connection up several levels — resulting in more meaningful interactions and deeper levels of attraction.
So if you want to step up your game here are some flirty questions to ask your crush today.
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Examples of Flirty and Funny Questions to Ask an Older Woman
1. When was the last time you felt butterflies around a guy?
2. If I asked to kiss your hand, would you allow it?
3. How do you know when you are truly in love?
4. How do you feel when someone gives you compliments?
5. What’s your favorite thing about yourself?
6. Do you have any secret romantic fantasies I should know about?
7. What type of music puts you in a mood?
8. If money were no issue, what is a fantasy date night that comes up on top of your bucket list?
9. If I were to write a love letter for you, what would be some of the things that I should include?
10. Are there any certain aspects of romance and intimacy that you hate?
11. What are your thoughts on long-distance romance?
12. Have ever had butterflies after meeting someone for the first time?
13. Have you ever been swept off your feet by someone much younger than yourself?
14. If I asked if we could go on a date tonight, would that be too forward of me?
15. What kind of activities do enjoy doing with somebody special?
16. If I had the chance to take you out tomorrow, what would be your ideal date night?
17. How do you think age affects relationships?
18. Are there any activities that make you feel especially romantic inside?
19. Is there anything about me that made you go “wow” at first sight?
20. Is there such a thing as too much romance between two people who are deeply in love with each other?
21. What kind of physical contact is most likely going to get your heart racing faster than usual?
22. Do you like holding hands and gazing into each other’s eyes?
23. If I sent flowers to your work, would that be too cheesy or sweet?
24. Do little romantic gestures like bringing coffee in bed turn you on?
25. If we were out having dinner together, what kind of conversations would we be having?
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26. When was the last time someone tried to surprise you or make you feel special?
27. If I asked to hold your hand, what would be your reaction?
28. What do you think is the most important thing for a successful relationship?
29. If I could take a peek into your heart, what would I find in there?
30. What’s been missing in your previous relationships that you are looking to explore?
31. If I were to kiss you, what would be your reaction?
32. What do you think is the most romantic thing a guy can do for you?
33. Have you ever had a crush on someone much younger?
34. What’s your favorite way to show love?
35. Do you prefer being wined and dined, or something more intimate when it comes to dates?
36. Do long walks along the beach sound like fun to you?
37. How has age changed how you look at dating and men in general?
38. Can love at first sight happen more than once?
39. How important is chemistry in a relationship for you?
40. Are there certain personality traits that make someone especially attractive to you?
41. If I wanted to impress you, what would be the best way for me to do that?
42. What’s something subtle but intimate I can say or do around you to turn you on?
43. Do you have any interesting stories from your past dates that you want to share?
44. Are there any unique qualities that make a guy stand out as an ideal romantic match for you?
45. If I looked into those beautiful eyes of yours, what secrets would they tell me?
46. On a scale of 1-10 how daring are you when it comes to love and romance?
47. Which song instantly brings back romantic memories for you?
48. Do older women have any advantage over younger girls when it comes to seduction?
49. How can I charm my way into your heart?
50. What kind of conversation topics turn you on the most?
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51. Do good looks give someone added advantage in dating or do personality and humor matter more?
52. What was the sweetest thing anyone has done to win over your heart?
53. When was the last time you stayed up all night talking to someone?
54. If I were to send you flowers, what kind of flowers would be your favorite choice?
55. Have you ever gone out with someone half your age before?
56. What do you think a perfect date night should look like?
57. If there were one thing that could instantly make you feel hot and confident, what would it be?
58. Have you ever had an unexpected romantic encounter while on vacation or a business trip?
59. Do you have any boundaries when it comes to intimacy?
60. Are you the type to take things slow or like to dive right into a relationship?
61. Have you ever had a fantasy about a younger guy before?
62. Do age differences matter when it comes to love for you?
63. Would you be open to exploring a passionate relationship with someone much younger than yourself?
64. Do you have a wild side that nobody else knows about?
65. How do you feel about the idea of someone taking care of all your needs and desires?
66. Is there anything that makes you feel especially feminine and hot when it comes to relationships?
67. Do you prefer it slow and passionate or wild and intense?
68. How often do you allow yourself to have fun with no regrets?
69. Are there any special techniques that you use to get a younger man’s attention?
70. How do you feel when a younger guy shows a romantic interest in you?
71. Do subtle touches make your heart rate increase or is it something more direct that gets your attention?
72. Would it surprise you if I said some of my fantasies involve being with an experienced mature woman like yourself?
73. Are you looking for a romantic adventure or would you prefer to take things slow?
74. What do you find most attractive in someone much younger?
75. How long has it been since your last romantic encounter?
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76. Are there any activities that make you feel really alive?
77. Have you ever found yourself daydreaming about an encounter with someone significantly younger than yourself?
78. Do you have any secret desires that make your skin tingle when you think about them?
79. If I asked for just one thing to set the mood, what would it be?
80. What kind of date would really make sparks fly between us?
81. Do you find it harder or easier to flirt with someone much younger?
82. Are there certain words or phrases that send chills down your spine?
83. Can I show up on your doorstep one day with an armful of roses just to surprise you?
84. Have you ever imagined what it might be like to have an intriguing affair with a much younger guy?
85. Do you find it easier to be more adventurous and spontaneous when dating a younger man?
86. Is there anything special about being older that makes dating more enjoyable?
87. When was the last time someone made you blush just by looking at you?
88. What type of conversations make you feel the most connected to someone?
89. If I was to tell you my deepest secrets, do you think it would bring us closer together?
90. Do you prefer getting attention from younger men or older ones?
91. What sets your heart on fire when it comes to romance?
92. Do you have any secret desires that you’ve always wanted to explore but haven’t had the chance to?
93. What do you consider your most attractive physical feature and why?
94. Why do you think younger men find you so attractive?
95. Do you feel comfortable taking risks when it comes to intimacy?
96. What do you think is the best way for someone younger to get your attention?
97. Have you ever been in love with somebody who was much older or more experienced than yourself?
98. Is there anything you’d like to explore romantically that you’ve been too shy or scared to do in the past?
99. How would you feel if I kissed your neck right now?
100. What excites you the most about an intimate connection with someone much younger?
101. Do people tend to underestimate how passionate and flirtatious you are?
102. Is it easier to seduce you with words, looks, or touch?
103. Have any other younger guys ever asked you on a date before?
104. How would you feel about getting away for the weekend and making some fun memories?
105. How does being desired by a much younger person make you feel?
106. Do you enjoy being sensual and intimate, or do you prefer being more adventurous?
107. What sort of compliments can help set the mood for you?
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