A lot of us grow very insecure and are often afraid of talking to the other gender. There are various ice-breakers you can use to calm down the tension. However, once you get to know them a little, you can start asking questions which dig a little deeper, and which can prove quite difficult to answer.
An awkward question is one which seems very innocuous at its surface but can be very tricky when you dig deeper in search for an answer. Every human has issues which bother them. A girl will always have various issues that will bother her like her weight, her age, intimacy, etc. Therefore, any question you ask along these lines will be considered awkward. While we do recommend you these questions, do remember that they are by nature awkward questions. You should always try to maintain a basic level of decency when you ask her these questions because they can backfire very easily.
Given below are a list of some of the best awkward questions we could think of. We tried to keep a plethora of occasions in mind. You can definitely ask these to a girl. It is to be noted that the questions which can be awkward for her can be awkward for you as well, so be prepared to answer if she asks you the same question.
1). Do you have any feelings for me?
2). Do you have any feelings for any friend of yours?
3). Would you trust me with a secret?
4). Have you ever stolen something from a hotel?
5). Have you ever lifted something from a shop?
6). Have you ever tried smoking?
7). Have you ever tried drugs?
8). Do you check your weight regularly?
9). How much do you earn currently?
10). What is the one moment you can never forget?
11). What is the single most embarrassing moment you have experienced in your life?
12). Are you currently single? (Are you currently seeing someone)
13). Do you love me?
14). How crazy would you describe yourself as?
15). What is the craziest thing you have done?
16). Have you ever taken part or done something you would never have thought of doing?
17). How would you feel about spending a night alone in a room with a stranger?
18). How would you feel about spending a night alone in a room with me?
19). Have you ever done something you did not want to do to get promoted? Did you get the promotion then?
20). Have you ever done something you did not want to do to get a job? Did you get the job then?
21). According to you, how long should one stay in a relationship before being intimate?
22). According to you, how long should one stay in a relationship before even thinking of getting married?
23). Do you a secret which you have not revealed to anybody?
24). What is a habit of yours that no one knows about?
25). How many relationships have you been in?
26). How many people have you dated in your life?
27). Do you have any pet peeves?
28). Is there any topic that makes you uncomfortable when it is brought up?
29). How spontaneous are you in your decisions?
30). What would you choose in life: stability in life or love?
31). Have you ever been so drunk you didn’t remember anything the next day?
32). Have you ever drunk texted anyone?
33). Have you ever drunk dialled anyone?
34). Have you ever done something while being drunk that you would not have done when sober?
35). Have you ever tried weed?
36). Have you ever done anything you shouldn’t have done when high on weed?
37). Have you ever done anything illegal?
38). What was the illegal thing you did? Why did you do it?
39). Have you ever had intimate thoughts about someone you shouldn’t have?
40). Have you ever had to reject someone when they made a move on you?
41). Has anyone ever rejected you when you made your move on them?
42). What is the worst breakup experience you have had?
43). What is the weirdest breakup experience you have had?
44). Why do you look so pale?
45). Do you believe in the gender spectrum?
46). What gender and sexuality do you identify yourself with?
47). Have you ever kissed someone for fun?
48). What is the strangest thought that has come to your mind while you were kissing?
49). What is the funniest thought that has come to your mind in a serious moment?
50). Can we hang out more?
Read also: Questions to Ask Your Crush
51). What is the best pickup line you have got?
52). What is the best pickup line that you have used?
53). What is the worst pickup line you have got?
54). What is the worst pickup line you have used?
55). Did you have a crush on any teacher of yours? What was it like? When was the crush? What did you do about it?
56). What is the longest duration of time you have gone without taking a bath?
57). Would you ever do something morally wrong for the money? If so, how much money would you want for it?
58). Have you ever had a bad experience in a club or a bar?
59). Has a girl ever approached you?
60). What was your experience while going through puberty?
61). Have you even been cheated on in a relationship by someone?
62). Have you ever cheated on someone you were in a relationship with?
63). What is the weirdest daily habit you have?
64). Have you ever had to fake your way out of a situation?
65). Have you ever given fake details about yourself to a guy?
66). What do you think about being in an open relationship?
67). What is the worst experience you have had when flirting with someone? Whose fault was it?
68). Do you feel safe with dating online?
69). How fast would you progress in a relationship with someone you met online?
70). What is the dirtiest joke you know?
71). Have you ever taken something which wasn’t yours?
72). Have you ever thought about being intimate with your best friend?
73). What is the naughtiest thing you have bought online?
74). What is the weird or uncommon thing you do to relax?
75). What turns you on the most?
76). What turns you off the quickest?
77). Have you ever used toys in a relationship? Have you ever wanted to? Which ones?
78). How kinky would you describe yourself as?
79). What is the one thing you want to eliminate from your life?
80). If you are asked to go to meet someone without makeup, how offended would you be? Would you actually do it?
81). What experiences would you want to have with your partner before considering getting married?
82). Have you ever left someone when they really needed you?
83). Has anyone ever abandoned you when you really needed them?
84). What is the weirdest thing you have spent your savings on?
85). Have you ever felt suicidal? What prompted you to feel that way? Do you still feel it?
86). What is the guilty pleasure you indulge in the most?
87). Have you ever been reprimanded for something you didn’t even do?
88). Have you ever tried to use your gender to get an advantage over the competition? Would you ever think of doing so?
89). Have you ever tried to seduce someone to get something you wanted? Would you ever think of doing so?
90). Have you ever experimented with your best friend?
91). What would your first reaction be if your parents saw you in a compromising situation with your partner?
92). What would your first reaction be if you saw your parents in a compromising situation?
93). How do you feel about showering with a person?
94). Have you ever regretted breaking up with someone in your life?
95). Have you ever regretted staying in a relationship with someone?
96). Are you willing to be in an open relationship?
97). Have you ever experienced harassment in public? Did you do something about it?
98). Which body part of yours is the most erotic for you?
99). What can your partner do so that you crave them immediately?
100). Have you ever thought of dating your male best friend?
101). Have you ever traveled anywhere without a ticket?
102). What makes you jealous when you see someone in a relationship?
103). Have you ever had a face-to-face experience with a fear of yours? What did you do? Did you get rid of the fear or does it still haunt you?
104). Would you consider being in a relationship with someone younger than you?
105). If you are ever held at gunpoint to kiss a guy who would you want it to be?
106). How do you feel about a threesome? Would you rather have two guys, or another girl?
107). Have you ever had a threesome? What was it like?
108). What is the kinkiest or most liberating thing you have done? Who did you do it with?
Read also: Questions to Ask A Girl
These are some of the best awkward questions you can ask a girl to get to know her better. You got to play the situation according to her answers and make sure you don’t make her uncomfortable. Something which would make all of this way more fun would be if you answered all the questions along with her. This will help reduce her discomfort and you both will form a better connection.