Dates can be awkward—but, fear not. Equip yourself with these stand-out questions for a first date and you’re ready for some moonlighting magic.

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One of the best ways to prepare for a first date isn’t what clothes you put on or where you make dinner reservations, it’s taking some time to think about what you want to talk to your date about.

As the saying goes, “you never get a second chance to make a first impression.” This especially applies to first dates. Generally speaking, if the first one doesn’t go well, there probably won’t be a second date, so you want to be sure that you show the best side of yourself. Doing this doesn’t mean inventing an untrue version of you, but instead showing your true self so that you can assess whether there is a real connection with the other person.

This can be hard to do on a first date. You’re nervous and you want the other person to like you. Thinking about what kinds of things you want to discuss with your date and getting to know their opinions and interests can help alleviate some of the nervousness and help you to show the real you.

Here are a few ideas for questions to ask your date that will make you stand out from the rest:

1. If you could travel around the world for a year all expenses paid, where would you go, what would you do, and how would you travel?

This will show you a lot about your date. Do they love to travel and experience other cultures? You will be able to assess their level of adventurousness, if they like to live the high life or rough it, and what kinds of activities and experiences get their attention.

2. Do you live to work or work to live?

What someone does for a living is extremely important. Whether we like what we do or not, we dedicate a huge amount of our time to work. This question can spiral into other conversations about feelings on doing what you love, finding out about their interests and hobbies and their life goals. It will also help you assess their values about work, personal life, money and other important issues.

3. What kind of teenager were you?

This is a question that most people aren’t asked on a first date. Who we are are as adults began to really take form in adolescence. This is when we began to see the world beyond ourselves and to form our sense of self and world view. Beyond giving you some insight into your date’s past, stories about adolescence are often a fun, lighthearted conversation where you can laugh and share embarrassing stories.

4. Do you like to read? Do yoga? Go hiking? Meditate?

This is an open question that you should tailor to your own interests. You don’t have to necessarily ask if a person likes to read, but if you have a hobby or activity that is important to you, you can ask your date about their interest in it. Maybe it’s something you can enjoy together on a future date. If not, this will open the door to ask your date about their interests and activities.

5. What is the worst first date you have ever been on?

Better not to ask this one if the date doesn’t seem to be going well, just in case your date answers, “this one!” If things are going well, talking about the worst date they’ve been on can be funny and it will give you some insight into your date’s preferences.

The most important first date advice you can receive is to be true to who you are. You’re not going to make a great connection on every date, and that’s okay. You want a true spark with someone, not something that is forced because you want to be liked. Let your true self shine through.

[image: via Nathan Rupert on flickr]