First dates can be so awkward. The nervous laughs, the desire to impress and the hope of finding “the one” is juxtaposed with the lingering memories of more bad first dates than good ones. And in that awkward and uncomfortable space, we make all sorts of bad decisions to avoid the unknown, like using alcohol to relax or sexual intimacy to connect. Suddenly, we are wrapped up in the idea of a romance with a person we don’t even know yet.

A month later, they are driving us nuts as we get to know them, but now they have a sock drawer at our house and breaking up is so hard and complicated. How did we get into this mess, and how can we avoid it next time?

Setting Boundaries Starts With Good Questions

Imagine having a fence around your garden with a locked gate. Every time you go out on a date, you open up the gate wide and invite someone in to enjoy your fruits before you know they are trustworthy. Unfortunately, instead of caring for your plants, they ravage your garden. You wonder how this could have happened. Did you need to build a bigger fence? No. You needed to be a better gatekeeper.

Boundaries are crucial on a first date, which is why it’s important to use the opportunity to gather information. Once you know more about someone, you can decide if they’ll be allowed to enter your emotional space. This act of gatekeeping protects our hearts and helps us to avoid making quick emotional decisions that cause more relational havoc.

Good questions can save you months of heartache if you listen to the answers and move forward based on reality (rather than an idealization of a Disney/fantasy relationship). So what questions should you ask? Here are four that you should try to cover on any first date.

1. What Type Of Relationship Are You Looking For?

This very direct question might surprise your date. Most people are used to playing games and waiting for months to discover the other person’s agenda. But really, why wait and get emotionally involved only to have your heart broken when could’ve gleaned this information on the first date?

To get an honest answer, ask this question with a big smile and in a non-threatening way: “I’m curious, are you looking for a relationship or something casual? Some people date looking for a spouse and others date to hookup; where are you on the scale?”

2. How Fast Do Your Relationships Progress?

Some people really like to move slowly at first, while others like to dive in when they think they’ve found something good. So ask your date, “How much time do you like to spend with a person when you first start dating them? Are you all in or do you like to take your time?”

After you listen to their answer, share with them how important it is for you to go slow, especially with someone you like. Taking your time and not jumping into a physical relationship will give you the very best shot at a lasting relationship. My husband Tim told me on the first date that if he had sex with me while we were dating, then he wouldn’t marry me. He laid his cards on the table and I liked and respected his honesty and commitment to purity. I appreciated his integrity and I knew exactly what I was getting into from the get-go.

3. Are You An Introvert Or Extrovert?

Find out if the person is a homebody or likes to go out. Are they last one at the party or the first to leave? This information is crucial in a marriage. My husband Tim and I are both extroverts. We close down every party – together. There are many personalities that complement each other in their differences, but extreme opposites in this area cause a great deal of conflict. When one person wants to stay at home and watch TV all weekend and the other wants to go out, someone is always disappointed.

4. How Do You Live Out Your Faith?

As a Christian, this question is crucial. A guy I once dated told me he was a “convenient Christian,” meaning he attended church when it was convenient and when nothing better was going on. His faith didn’t direct his life; it was an add-on type of faith. That wasn’t going to work for someone like me who is a fully devoted follower of Jesus. I was looking for a Godly man whose life was Christ-centered.

Remember, these first date questions aren’t meant to judge. They are simply meant to clarify if this person is a good match for you. Have fun and enjoy meeting a new person on your date, but if they do have the answers you are looking for, sit up and pay attention. It might be the one! I knew my first date with my husband was something special because I didn’t want it to ever end.

You may also be interested in 3 Places To Meet Women & Men With Real Relationship Potential

  1. You forgot the main question a man needs to ask a woman early on. Does she like to cook, and is she good at it! All the Christian psychobabble will be for nothing, if hubby is being neglected in the kitchen. You can live without self improvement books, but you cant live without eating.

  2. How about do you put out on the first date, I mean get right to it no sense in wasting time & money just to go home frustrated.

  3. Quoting you, “…why wait and get emotionally involved only to have your heart broken…” Exactly right! Asking good questions on a date is a great idea; however, there is a way to ask tons of questions before going on a date, thus avoiding a risk of getting emotionally involved with the wrong person. Everyone should use Self-Match before going on a date. It makes SO MUCH sense. What do you have to lose? Just give it a try while it is free.

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