Thirty Conversation Starters for the First Five Dates

Conversation starters. Sometimes we all need them.

Especially when you finally sit down with that first date, and your mind goes blank because you’re distracted by how cute they are! I put together this list for people who have a hard time knowing how to kick off a good date discussion. You can use this as a reference list, pull just the ones you need, or simply compare with your conversations on your dates so far. 

This list is in a general chronological order, by the way. The further you read down, the more personal and potentially serious these questions get. So along with helpfully titled categories, I have included notes of when it’s appropriate to bring them up to your date! (Obviously, this is a very general timeline, and every relationship is different. Do your best.)

For Breaking the Ice:

These are great to use from messaging, to phone calls, to video chats, to the first couple of dates! Think of them as springboards to shake off jitters and dive into chatting. And you can always reuse them on subsequent dates, if you want a running game…

1. If you had to fight one horse-sized duck or one hundred duck-sized horses, which would you choose?
2. Tell me something weird that happened to you this week! (In my case, my houseplant sprouted a flower in the middle of winter.)
3. Would you rather be completely nocturnal, or never have dessert again?
4. Name one store where you have never been shopping.
5. What was your last order at a restaurant?
6. Guess what color my socks are right now. (Bonus points if each of your socks is a different color!)

For Getting to Know Each Other:

These are safe to bring up on the first couple of dates. If you’re trying to get to know someone over a long distance, these are also okay to bring up on the second or third video chat! Just don’t lead with these on a message board, it’ll come on a little strong…

1. Have you taken the personality test on CatholicMatch? How accurate do you think your results are? (Mine were spot on, I’m absolutely a combination of phlegmatic melancholic!)
2. If you had a whole weekend free, what would you do with the time?
3. Who are your role models at work, in faith, for hobbies, etc.?
4. Describe your family dynamics in just two words! (I would describe mine as a walking musical. Or harmlessly crazy.)
5. How did you meet your best friends? What do you do together?
6. Describe your school/job: is it awesome, or do you want to switch fields in the future?

For Digging Deeper:

Not to be used with still-strangers! Save these questions until at least the third date, when you know each other better and have some mutual attraction going on. Warning: these conversation starters could get you on the path to becoming an official dating couple!

1. What’s one of your most profound memories about prayer?
2. Are you a money saver or a money spender? What do those words mean to you?
3. What’s the most helpful thing you learned from your parents? What’s the least helpful? (Mine taught me the value of hard work, and also that a group of butterflies is called a “flutter.” Who knew?!)
4. How would you handle a career change, if you ever wanted one?
5. When and how did Catholicism become important to you?
6. Name a couple you know who have a great relationship: what are they doing right? (One of my favorite couples always finds something to laugh about together!)

For Romance—Past and Future:

Now we’re getting into territory you should bring up when you’re considering being an exclusive couple. Right around the time you start “going steady,” these questions are easy lead-ins to those important topics!

1. What was your best date? What was the worst?
2. Name three good reasons and three bad reasons to break up with your boyfriend/girlfriend. (This could be your own personal experiences, or a theoretical discussion!)
3. How does your faith influence your dating life? 
4. What’s your perspective on physical boundaries in dating? (E.g., hand-holding, hugs, kisses, signs of affection . . . and yes, sex too!)
5. Tell me about your experiences with children, both positive and negative.
6. What’s an unexpected lesson you learned through dating? (I discovered that “the spark” is a very real thing…)

For Tough Topics:

Please be seriously dating before bringing these up. These touch on vulnerable, serious topics to address with someone you’ve built trust with overtime! For example, this should be territory to explore after date four, AND well before you talk about relocation, engagement rings, or wedding bells.

1. Tell me about your worst mistake in life, and what you learned from it.
2. How do your financial habits affect your life, such as debt repayment?
3. What is your experience with pornography, if any, and how do you deal with it? (Caveat! The question “do you view pornography?” can be asked as early as the first date. This question about experiences and recovery is meant to discuss a history of addiction or exposure, if someone has been through it.)
4. Describe your exes and why the relationships ended.
5. What’s something I should know, but hasn’t come up in conversation yet?
6. When do you think spouses should end a marriage? (This will give you both a good idea of how you view the permanency of marriage, as well as digging into annulments and divorce.)

There you have it, an easy list of ideas to get the ball rolling with your date!

I would like to add: the most important thing when you use these conversation starters is to have your own answers ready. It’s only fair to answer exactly what you ask! And really, that’s the point of conversation starters—so you can mutually learn more about each other. Dates are not interviews, but a chance to connect and communicate with a potential love interest. So go forth and date bravely!