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Eight Questions to Ask on a First Date, Part Two

First dates don’t have to be filled with awkward silences or polite chit-chat. It’s possible to have a great time learning about a guy (so you can decide whether a second date is in order), while ensuring your date has a blast, even if you’re never going to see each other again.

This week’s Friday Takeaway is part-two of my month-long series What To Ask On A First Date. Last week I told you how to find out if he’s loyal, and if the two of you share the same sense of humor. This week, it’s on to how to suss out his goals in life, and how to determine if he’s as ready for adventure as you are!

3. To Find Out if He’s Adventurous

Years ago,I started a business with zero capitol. I did it on drive alone. Most of my friends (who could easily be considered “adventurous” because of their desire to travel to exotic locations) thought I was nuts to take such a giant leap of faith. So, being “adventurous” can mean many things. Here are a couple of ways to get at what kind of adventure he seeks, if any.

Where was the last place you traveled? You can also ask him if he roughed it or went five-star all the way. But being adventurous doesn’t have to refer to just travel, it can also describe a guy who likes to try new and unique restaurants and food, for example. So you can modify this question to something like: weirdest thing you ever ate, or strangest party you’ve ever been to, most interesting city you’ve visited. The idea is to determine how willing he is to try new things, and whether that compliments you’re own willingness.

An alternate approach is to ask: What was the biggest decision you’ve ever made? He may not be the guy who will climb Mt. Kilimanjaro, but maybe he’s a guy who takes a risk in business or for something he really believes in. You can follow up by asking him more about that decision. Why was it so big? What was challenging about it for him?

4. To Learn About His Goals In Life

What do you love most about your job? You want to use this question to find out if he’s living his dream. If he says “I’ve wanted to be an accountant since I was a little boy” that tells you something about what he’s aiming for. If he says, “Oh no, I’m only in my day job because I’m writing a novel on the side,” then you get a greater insight into what makes him tick.

It’s time to start taking a closer and deeper look at the men you’re meeting. These questions may seem light, but if you ask from a place of genuine sincerity, you’ll start to make more meaningful connections out there. Next week, we’ll cover questions to help you find out if you’re compatible, and if he’s a commitment-phobe.

I want to know how this series is serving you! Leave your comments and questions right here on the blog and feel free to share this with your friends!

Read Part Three of Eight Great Questions Right Here! on the Friday Takeaway.

Wishing you New Beginnings and Lasting Relationships!
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