"It pretty much goes without saying that dating can be hard. Putting ourselves out there, opening up, and being vulnerable to something new takes effort and time. Add in being a single parent, and the task goes from nerve-wracking to downright risky. Not only are we putting our own hearts on the line, but at some point, our kids will likely be involved as well. The thing about dating, though, is that it’s supposed to be fun. Connecting with someone new for the chance of having it work out can sometimes be a risk worth taking.
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Once we’ve put ourselves out there and said “yes” to that first date, now comes the time to prepare. It doesn’t hurt to ask ourselves some important questions, like what we’re hoping for the outcome of the date, and what our future relationship goals look like. Once we have those answers nailed down, we can prep ourselves even further. And the best way to curb some of those first-date jitters is to have some topics on hand to discuss so the conversation never lags.
That’s why we’ve put together this list of first date questions for single parents to ask. They range from fun ice breakers, to get to know you inquiries to getting-down-to-business deep dives, so whatever your relationship goals, you’ve got what you need to make the first date a success.
First Date Questions for Single Parents
Fun Icebreakers
When it comes to first dates, what gets our nerves going more than anything is typically the lingering question: What do we talk about? The best way to get the nerves at ease is to have a few fun icebreaker questions on hand. These are meant to spark fun conversation and maybe share some laughs to make the date enjoyable.
Here are some creative first date questions to consider:
1. If you could put together your perfect line-up for a musical festival, who would your top five artists be?
2. You can travel anywhere in the world tomorrow—where would you go?
3. Favorite TV show or movie you’ve watched recently?
4. What’s your dream job? Are you currently doing it?
5. If you could relive one day in your life, what would it be?
6. What’s something about you that might surprise people?
7. What does the perfect date night look like to you?
8. What’s the comfort show/movie you could watch over and over again?
9. What’s your go-to drink order?
10. If you were to host a podcast, who would your dream guest be?
11. If you could be a contestant on any game show, what would it be?
12. What’s your go-to karaoke song?
13. If you were to get a tattoo (or another), what would it be?
14. What’s your favorite holiday and why?
15. What would you do if you won the lottery tomorrow?
16. Would you rather see what’s in outer space or the bottom of the ocean?
17. If the world ended tomorrow, how would you spend your last day?
18. If you could meet one fictional character, who would it be and why?
19. When you were little, what did you want to be when you grew up?
20. What’s one book you think everyone should read?
Get to Know You Questions
Fun stuff aside, the first date is a great time to get to know someone on more than a surface level, especially as busy parents. Use these get-to-know-you questions to get a better picture of who they are, what they value, and what dating them might look like in the future.
1. Where did you grow up? How often do you get back there?
2. Are you a morning person or a night owl?
3. What’s a typical family gathering like for you?
4. How do you like to relax at the end of the day?
5. Are you more introverted or extroverted?
6. What are your favorite hobbies?
7. What are your goals for this year?
8. Do you like to cook/what’s your favorite dish to make?
9. If you could make the world better in one way, what would it be?
10. What’s your love language?
11. What’s something you learned recently?
12. Who are your biggest role models?
13. Do you have or want any pets?
14. What types of places would you like to go on family vacations?
15. Go out on a Friday night or stay in?
16. Are there any outdoor activities you enjoy?
17. Would you consider yourself always on the go or more of a homebody?
18. Would you rather spend a week in New York City or Yellowstone National Park?
19. How do you handle stress?
20. Do you have any phobias?
Getting Down to Business
It’s hard enough to get vulnerable while dating as a single parent. Not to mention the time it takes to get to know someone new. If you’re going into a new relationship to determine early on if you have a future with the person on the other side of the table, pull out some of these eye-opening questions.
1. Do you want (more) kids?
2. What three words would you use to describe each of your kids?
3. Who do you go to when you need advice?
4. Are you close with your family?
5. Do you have a job that requires you to travel a lot or may require you to relocate in the future?
6. What’s your relationship like with your parents?
7. When you feel big emotions like anger, frustration, or sadness, how do you typically deal with those and regulate your emotions?
8. How often would you like us to see each other in any given week?
9. How often would you like for us to communicate with each other when we’re not physically together?
10. Do you have any religious beliefs you feel strongly about?
11. When it comes to politics, is there anything I should know about your beliefs?
12. Here is my situation with my child’s other parent and how involved we are in each others’ lives… How do you feel about this?
13. How’s your relationship with your child’s other parent?
14. Where do you see yourself in five years?
15. Why did your last relationship end, and what did you learn from it?
16. What are you looking for out of dating?
17. Do you have a desire to get married in the future?
18. How do you handle conflict with a romantic partner?
19. When was the last time you said “I love you” to someone you’re not related to?
20. What do you think is the most important lesson to teach children?
21. In a relationship, what are your deal breakers?
22. What qualities do you look for in a significant other?
