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5 First Date Questions Single Christians Should Ask

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5 First Date Questions Single Christians Should Ask – Plus 5 self-reflection questions you should ask after the first date.

A few years ago, Stacy approached me to help lead a singles’ life group based out of our local church, James River. It had been a while since I had commingled on a deeper level with other single Christians outside of work and general church service.

Life groups eat together, talk about real-life issues, and get involved in each others’ messy lives.  I was excited to venture out again in establishing some great new friendships.  Normally life groups are made up of 5-25 people.  Ours meets Sunday evenings at a host’s house for lite snacks and conversation.  The first night saw less than ten new participants with an uneven ratio of men to women.

Our third meeting was the most interesting thus far.

Being a very casual event we waited for a little after the start time in hopes a few more people would arrive. Ten minutes later we prayed, grabbed some food, and all finally took our seats. That night I would be the only guy to show up.

It’s not abnormal for me to be outnumbered by the women in my life. I have two sisters, two daughters, three nieces, and five great-nieces. And now, a group of incredibility smart single women who all looked like they had a lot on their hearts and mind.

The conversation swung around to dating. And of course, I opened my mouth; it’s a problem, I know. Some of my female friends often ask the same cookie-cutter questions when they have men in front of them that are dating neutral: “Why do guys….?”

Dating 101

As I have mentioned before, in the last decade I have had the opportunity to go on many first dates. It was a good way to settle inside myself what and if I wanted something more substantial with respect to relationships and marriage. I had the opportunity to meet and talk to many different types of women both in personality and beliefs.

When dating, I learned early on that I needed to better prepare and intently listen if I wanted to truly appreciate the conversation and evaluate the potential of the date. To help propel the preparation I developed a list of basic questions. These questions were progressive in nature and were freely integrated into the conversation where appropriate. Today, that list exceeds 200.

That evening I blurted out I had a list. Sure enough, there were tons of questions about the questions.  I explained there were obvious questions that are normally asked on a first date that some answer favorably. My questions were built to uncover what they don’t tell, the lie detector for date one.

Failure to uncover things within the first few dates can get some singles in trouble with establishing boundaries as things progress. The lack of good boundaries allows false trust to enter. Subsequently, bad behavior may be overlooked leaving the heart exposed, crippling the ability to easily walk away. You need to ask good questions in order to discover the person in front of you before your hearts starts to lean toward or fall for them.

Framework for Questions

First, I never announce to a date “hey, I have a list of questions that you have to answer before I can date you.”  Rather, I introduce them strategically in conversation and take mental notes for later. I mention some of these tips in my article Online Dating Tips for Single Christians.

Second, these questions are progressive in nature and are always done in person. There are first date questions and ones after.

Third, sometimes questions can come across as expectations by the way they are phrased. While in reality, some are, the focus should be on non-negotiable responses.

Finally, be prepared to test things. A person’s character can’t be trusted until it’s been tested, and testing means asking great follow up questions and then observing actions. If they seem offended or taken back by your questions, this could also be a sign of how they resolve conflict.

These questions are to be introduced into a common conversation. You don’t have to follow any order; however, the first few are more ice breakers.

5 First Date Questions

1. Who is your best friend? What do you like about him/her? – 5 First Date Questions

This question uncovers the depth of friendships in their life. It’s very common for women to have very deep emotional female friendships. It is uncommon for men to have deep emotional friendships with other men. What you are looking for is the emotional and intellectual depth that aligns with yours. Also, they have people involved in their life.

2. Tell me about your family growing up? – 5 First Date Questions

I am a firm believer that there is no wrong answer to this. What you are looking for here are the things you are comfortable with that coincide with your history. This is a great way to get them talking. Remember to simply listen and respond with kind banter.

3. What do you think is the biggest mistake that men/women tend to make in relationships? – 5 First Date Questions

This will tell you a lot about what turns them off and about their attitude toward the opposite sex in general. You can also determine their position in leadership. Do they like to lead a relationship or are they a follower? This will also reveal their general mindset and expectations. If they speak of things that are unrealistic, and the relationship moves forward, you may have to deal with unrealistic expectations. This is a great place to ask good follow-up questions.

4. Tell me about your beliefs? – 5 First Date Questions

With this question, you can get a sense of where they are in their walk with Christ and their core values. If their beliefs and values don’t align with biblical truth, then this provides great insight to not move forward to a second date.  This is also where you will find out HOW Christian they are. Do you believe in abstinence before marriage? Drinking? Smoking? Dancing? All of these things are revealed with this question. Spiritually speaking, you are always looking for someone who is at the same level or who has greater maturity.

5. Have you ever had your heart broken? – 5 First Date Questions

The broken heart question is by far one of the ones that uncover the most for me. It should be asked at the correct time when past relationships naturally enter the conversation. We have all had our hearts broken one time or another. So the answer, unless you are 16, should be yes. Special attention to words is necessary during this part of the conversation. It’s OK to see a sense of remorse and for them to take personality responsibility for their heart. What should be closely observed is the direction they take and if it turns negative. A person who has worked through their past takes personal responsibility for it; while those who haven’t, haven’t.

If you are observant, this question will reveal if their heart is tied to the past. This is also where you will see them blame someone else for their “single” position.

At the end of the day, if it is raining out and I choose to go outside without an umbrella, I am going to get wet. I can choose to take responsibility for not bringing the umbrella, or blame the rain. Most will blame the rain. Personal responsibility for one’s heart, mind, body, and spirit regardless of external forces is one of the most important qualities I observe in successful relationships and marriages.

Repetitive Broken Hearts

Finally, if you have someone in front of you who has had their heart broken many times, this may be a red flag. As you closely observe you may find that they have an issue with guarding their heart and emotional judgment in dating. These are the people who easily fall in and out of love multiple times. They find themselves the victims rather than victorious in singleness.

Having a simple set of questions allows you to start to get a clearer picture of the person in front of you. They may answer each question to your pleasing, but it doesn’t stop at these five. You will want to continue to ask good questions about who they are and how they do life. This also means that you must ask yourself the same questions. Any date that has answered these questions for me almost always asks for my answer. Be prepared.

If you decide to move forward with a second date, you can start to ask some self-reflection questions to test each interaction.

Here are some self-reflection questions to ask after each interaction, past the first date:

  1. Do they demonstrate Godly character?
  2. Do they honor me?
  3. Have they shown genuine respect for me?
  4. Can I be me around them?
  5. Do we have similar life goals?

Dating isn’t a destination. People can sense if you are more concerned about the destination of relationship and marriage than you are about knowing who they truly are. Asking great questions allows you to do both. They enable you to see things clearly while plotting a course for the future. “Remember when…” is always something that strong couples do when they reflect on their dating and life experiences together. They look at the past with fondness. This is your opportunity to create those great memories with someone.

Happy dating…

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