Eliminate the boring dialogue of your favorite color and dig deeper into these memorable questions to ask on a first date. Sometimes a first date feels more like an interrogation than an opportunity to connect. How many times have we met someone for the first time and felt like our date was carrying a clipboard with detailed notes about us The art of the first date is to come up with engaging, thoughtful questions that encourage the conversation to flow. The information coming from this type of interaction is so much richer and much more natural. Here are five fun questions that make conversations wonderfully revealing and rewarding

What do you do with your free time

This simple question says a lot about a person. For example, if your date is spending Sunday at the office, that’s an indication that work is a priority. If your date regularly trains for marathons, this indicates a high commitment to fitness. The key to extracting good information from this question is to ask how your date spends free time rather than how your date would like to spend free time.

What are your goals, passions and dreams

Although this is a huge question, it is important. 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 towards a promotion that will involve logging in more hours at the office when her dream is to stay home with a family  It’s like the ‘umbrella of life’ question because that’s what drives people. One of my passions is authentic travel . My goal is to make it a bigger part of my business, so that I can share the benefits of the trip with others. My dream is to organize retreats where responsible and sustainable travel can complement a playful and mindful program. All of these elements align and fit perfectly with my husband’s desire to retire to a coastal community.

What are you laughing about

Although this seems like a dumb question, it is helpful, especially when “sense of humor” is so prevalent in online dating profiles. We all want to have a good laugh and we all want others to appreciate our humor. No big deal, right Well actually… there are a lot of styles of humor 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 enjoy, instead we let it flow. Luckily, we both have humor that we enjoy individually, and we also have certain types of humor that we enjoy together. Better find out early what tickles the funny bone on your date.

What kind of environment did you grow up in

This is another reason because it allows you to tap into the family dynamics and relationships that developed during childhood. It’s also a great way to see how your date has begun to formulate life values. And, the literal environment is an important part 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 he appreciates animals is very different from mine. We’ve talked enough about it to see everyone’s points of view – and to appreciate them. However, without the background information, it would have had no context.

What type of relationship is important to you

Although it may seem redundant to ask, as this information is part of the online profile, it is good to check on this. Not everyone is authentic with this on dating profiles and it can be vulnerable information to reveal on the internet. Moreover, it really is a topic that lends itself better to face-to-face dialogue. Sometimes things change, so this one is worth revisiting on later dates – if there are any! Neither my husband nor I wanted to remarry when we met; however, on the first anniversary of our first online communication, we did. You really can never tell where the heart will take you!

Wherever the questions and answers lead, be fully present when you engage, so even if your date doesn’t come on time, you’re both human beings sharing a vulnerable situation. Being kind is always the best way to approach and appreciate attempts at genuine connection. Also, you never know what might happen in the future as a result of this experience – sometimes the second date is much better than the first, but that’s another article entirely!