- Who are your closest friends? This is a nice way to begin since it lets your date discuss things in her comfort zone while not getting too personal. Moreover the answer can also tell you a lot about the kind of person she is. For instance if her closest friends are all from high school, it indicates that she values loyalty in relationships and is wary of change.
- How many siblings do you have? This question offers a safe way to know more about her family. If she comes from a supportive family, she will probably tell you a good deal about her parents, siblings and even cousins and grandparents. But if she appears vague and wishes to change the subject, then it would be best not to prod her more since she might have had an unhappy childhood.
- What is the best vacation that you took? People usually love talking about holiday they took in another country or the roaring time they had on the beach over the weekend. Encourage your girlfriend to talk about what she liked most of all on that particular vacation and you might get an insight into her favorite kind of getaway.
- What are your favorite colors and why? Being a fun question, this is bound to leave your date giggling and taking her time over several suitable options. And if color therapists are to be believed, one’s favorite colors could also offer clues to the kind of person she is. That is of course, if the colors your date mentions are actually her favorite and she is not carried away by the spirit of the game.
- Are you an outdoor/indoor person? Ask your date if she prefers to spend her spare time pottering in the kitchen or if she can’t wait to hit the road to the countryside. In fact an insight into this aspect of your girlfriend could even help you plan future dates like a quiet dinner with romantic music for a homebody or a rock-climbing event for the sporty girl.
- What are your ambitions as far as work is concerned? Even though this may sound too much like being interviewed for a job, it will give your date a chance to talk about her professional ambitions and her aspirations for future.
- What about your pet peeves? You may be surprised at the number of unexpected things that may crop on this one – wet bathroom floors, soggy sandwiches, Lindsay Lohan stories in the media, weekend traffic on the way to her family home, lizards… the list could go on.
- What do you like most about living in the present times? While there are no end to complaints like pollution and rising gas prices, coming up with all that is nice about the present might give her something to think about. And best of all, it could act like a feel-good pill for you both.
- Who is your favorite actor/band/celebrity? This is a common conversation starter on most first dates. But apart from knowing what kind of music and personality your girlfriend identifies with, the answers will give you ample date ideas for the future. For instance, you could earn huge brownie points by surprising her with tickets to a concert playing her favorite band or to a movie which has her favorite actor.
- How do you spend your week? Knowing what someone does during non-working hours would give you an insight into her priorities. For instance your date might put in a 40-hour week at work, but if she still has the time and energy to hit the gym thrice a week, you know that health and fitness score high with her.
- That hairstyle/outfit really suits you. Where did you get it? In all probability, you date knows that you are not terribly interested in where she does her shopping. But just the fact that you noticed something nice about her and asked about it would make her really happy. A lot of girls work really hard on appearances and there is nothing like a sincere compliment to brighten their day. However avoid any comments with sexual overtones or you will come across as a jerk.
- If you could play a part in a movie, what would it be? Her answer might be Audrey Hepburn’s role in romantic classic The Roman Holiday or a more spunky character like the eponymous heroine of Erin Brockovich . Whatever it is, the reply would surely allow you a tiny peep into her fantasies.
- What is your happiest memory from the past? Most likely it will be an account of a childhood picnic or an afternoon at the zoo when she was seven. However if she has had an unhappy upbringing, she might talk of the time when her science project was appreciated at school or she bunked class to catch a movie.
- What is your favorite food? This question might get her reminiscing about large hearty family meals or she may rave about the delicate flavors of Japanese cuisine. Either way food makes for a great conversation topic.
- When was the last time you planned a surprise party for a parent/friend? This might make for a hilarious set of memories but don’t get unnerved if she mentions that the she last one she did was for her ex.
- Tell me about one of your most embarrassing moments. It could be the time when she got drunk and threw up at a friend’s bash or got her ex’s mom’s birthday wrong.
- When upset, what do you usually do to feel better? This question might be slightly premature on a first date but on your next outing, you could pose the question to get a glimpse of the person within.
- What are your life goals? Again more appropriate when you are getting to know your date better, this one could make you come across as a sensitive man interested in knowing the real person behind appearances.
- What was the last book you read or movie you watched? Follow it up by asking if she liked it and why.
- Should we do this some other time? The answer to this of course will determine whether you get to put any more questions to her in future.
No matter how witty your questions are, it means nothing unless you are actually listening to her answers. Asking questions for the sake of carrying on a conversation or to make yourself appear smart will quickly turn boring. So let the questions be the first step in getting to know her well but also follow it up with a genuine interest in what she has to say.
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