Top 5 Best and Worst Questions to Ask on a First Date

Congratulations on getting a date with the woman of your dreams! But now that you’ve gotten her to go out with you, where do you go, how do you act, and what the heck do you talk about? For starters, I recommend that you pick a quiet but informal place to get to know her, such as a restaurant or park, and remember to ask as many open-ended questions as possible in order to encourage further discussion. There are a few subjects that you should definitely stay away from, but we’ll get to those later. Here some guidelines for great conversation starters that will get the ball rolling:

1) How was your day today? This may sound like an obvious one, but it’s more important than you might think! Many people forget these common courtesies in the anxiety of a first date. By asking your date what her day was like, you can show in interest in her life as well as gain insight into the kind of activities she does on a daily basis. This will also help to break the ice by allowing her to establish a sense of familiarity with you.

2) Tell me a bit about the relative you feel the closest to. This is a great way to quickly identify your date’s interests and values without having to ask her about them outright. Hearing her describe all of the important people in her life will allow you to learn more about her family and background, as well as put her at ease in your presence. Once she opens up to you about her family, it can also lead the discussion toward other family-related topics and stories, which are always great to talk about on a first date because they imply an interest in long-term commitment.

3) What are your favorite books and movies? This is an easy way to connect with your date, as most everyone has read at least one book and seen at least one movie. If your date doesn’t have any very strong preference for any books or movies, try asking about something else, such as her favorite foods or places. You’re bound to find something that can help you relate to her, and identifying common interests is a great way to bond on a first date.

4) What do you think is the most disgusting food ever? It’s a good idea to bring a funny topic into the conversation to lighten the mood a bit. Asking questions like these are an easy way to get her to laugh if you’re not very good in the humor category. Consider sharing a funny story from your childhood with her in order to get her to open up. You can also tell her about your most embarrassing moment, and ask her to describe hers.

5) What is your dream job? A woman’s dreams and goals really say a lot about her. Since it would obviously be a little awkward to ask her outright about her life goals, frame the question in a more lighthearted way by asking about what job she would choose if she could have any one in the world. The answer will probably be something like a singer or model, and then the conversation will segue naturally into both of your actual dreams and aspirations.

Now, for what not to ask on a first date:

1) What kind of relationship are you looking for? No, no, no! You always want to stay away from questions that are too interview-like or personal. A woman will interpret this question as “What type of relationship do you want with me?”, which is something that she won’t be ready to answer on a first date (and shouldn’t have to). If she wants to bring up what kind of relationship she is looking for, that’s fine, but for your first date just focus on having fun and getting to know one another.

2) Have you ever had your heart broken? Another downer. This is just too invasive to ask on a first date, especially because of the fact that heartbreaks are usually very personal situations. Nobody wants to spill all of the details of their heartbreak story to someone they don’t even know very well, not to mention that it will bring the whole tone of the date down. In general, you want to stick with upbeat topics on a first date and focus on your future together, not your past.

3) What do you think is the biggest mistake that guys make and why? This is just a sneaky way of getting your date to reveal her deal breakers on the first date. This question will likely just launch your date into a long rant about all her crummy past boyfriends. And, as stated in the section above, it will get you guys talking about your dating past instead of your dating future. Why would you want to spend your first date just listening to her complain the whole time?

4) What do you look for in a guy? Excuse me while I throw up. I cease to understand why people stick to boring, cliched questions on first dates. Let’s play this one out, shall we? You ask what qualities she looks for in a partner, she rattles off a bunch of generic traits such as kindness, generosity, and trust, and you say “oh” and don’t learn anything new that you didn’t already know before. What do you think she’s going to say, anyway? That she looks for losers with bad attitudes? This question is just cheesy and unoriginal.

5) Are you usually the dumper or the dumpee? First of all, I never recommend using the word “dump” when referring to a human being, especially on a first date! Most women hate being asked this question because they feel like they’re being judged. And the truth is that they are. If they say that they’re usually the “dumper” you’ll think they’re a heartless bitch, and if they say “dumpee” you’ll think they’re a desperate loser. So just take my advice, and don’t force your date to go into the details of her past relationships. You wouldn’t want her doing it to you, would you?