in: Dating & Relationships

5 Memorable Questions to Ask on a First Date

Do away with boring what’s-your-favorite-color type dialogue and dig deeper with these memorable questions to ask on a first date à la Amy Angelilli.

Sometimes a first date seems more like an interrogation rather than an opportunity to connect. How many times have we met someone for the first time and felts as if our date is carrying a clipboard keeping detailed notes on us? The art of the first date lies with offering engaging, thoughtful questions that encourage conversation to flow. The information from this kind of interaction is so much richer—and a lot more natural.

Here are five fun questions that make for wonderfully revealing and rewarding conversations:

  1. How do you spend your free time?

    This simple question reveals a lot about a person. For example, if your date spends Sundays in the office, that’s an indication that work is a priority. If your date regularly trains for marathons, that’s indicates a big commitment to fitness. The key to mining good information from this question is to ask how your date spends the free time rather than how your date would like to spend free time. If he says he’d like to be studying for the GMATs but in reality he’s spending his free time playing video games, that’s a big reveal. It also helps to see if your free time is compatible. I’m involved with improvisational theater and my husband is in a band. Our rehearsals fall on the same night, so it works out beautifully.

  1. What are your goals, passions and dreams?

    Although this is a huge question, it’s an important one. What if the person has no goals, passions or dreams? Or, what if they don’t complement each other? For example, what if she is working toward a promotion that will entail logging in more hours at the office when her dream is to stay home with a family? This is like the “umbrella of life” question because it’s what drives people. One of my passions is authentic travel. My goal is to make it a larger part of my business, so I can share the benefits of travel with others. My dream is to host retreats where responsible, sustainable travel can complement a mindful and play-based program. These are all in alignment and also fit nicely with my husband’s desire to retire to a coastal community.

  1. What gets you laughing?

    While this seems like a silly question, it’s a useful one especially when “sense of humor” is so prevalent in online dating profiles. We all want a good laugh and we all want to have others appreciate our humor. No big deal, right? Well actually…there are a lot of humor styles and they may—or may not—be compatible. When I first started taking my husband to improv shows, his reaction was always, “I don’t get it.” Whoops! We never actually discussed the humor we appreciate, instead we just let it unfold. Luckily, we both have humor we enjoy individually and we also have some types of humor we enjoy together. (Thank you Portlandia!) Better to find out early what tickles your date’s funny bone.

  1. In what kind of environment did you grow up?

    This is another biggie as it enables you to tap into the family dynamic and the relationships that developed during childhood. It’s also a great way to see how your date started formulating life values. And, the literal environment is an important element of your date’s life and can affect the lenses through which life is viewed. My husband grew up on a farm, so the way in which he appreciates animals is much different than my own. We’ve talked about it enough to see each other’s views—and to appreciate them. However, without the background information it wouldn’t have had any context.

  1. What kind of relationship is important to you?

    While it may seem redundant to ask, as that information is part of the online profile, it’s good to check in on this. Not everyone is authentic with this on dating profiles and it can be a vulnerable piece of information to reveal on the Internet. Plus, it really is a topic that lends itself better to face-to-face dialogue. Sometimes things change, so this is one that is worth revisiting on subsequent dates—should there be any! Neither my husband nor I wanted to re-marry when we met; however, on the one-year anniversary of our first online communication we did just that. You really never can tell where the heart will lead you!

Wherever the questions and answers lead, be fully present when engaging so even if your date doesn’t hit the spot, you’re both human beings sharing a vulnerable situation. Being kind is always the best way to approach, and appreciate, attempts to authentically connect. Plus, you never know what might happen in the future as a result of this experience—sometimes the second date is way better than the first, but that’s another article entirely!


[image: via Joao Paulo de Vasconcelos on Flickr]

About the Author:

Amy Angelilli

Amy Angelilli: Chief Adventure Officer – The Adventure Project Amy Angelilli’s own adventure project began when she turned 40 while on safari in South Africa. Realizing she had veered off the path of her “right life,” she returned determined to make major changes both personally and professionally. In the first half of 2012, she left her relationship, her house and her job. In the second half of 2012, she married the love of her life–one year to the day she unveiled an authentic, heartfelt profile on a dating website. Her latest creation is The Adventure Project, which offers relationship, life and travel adventures to the Every Person via play. When not playing or navigating adventures, she can be found enjoying meaningful travel, restorative yoga or improvisational theater. Her greatest performance is as herself in “It’s All About Amy”–the unscripted story of her life. She also created and produced the theater experience “3 Blind Dates”–Denver’s only unscripted romantic comedy that showcases the phenomenon of modern dating. Follow her authentic adventures on twitter or via her blog and you just might find your own adventure!


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