Whether you are making conversation with a new Tinder match or trying to converse on a first date, we have all had those awkward, conversational-halting moments. I’ve had my fair share of first dates and matches on dating apps and holding a conversation doesn’t need to be that hard. I get it: sometimes you feel like you have asked all questions possible and the conversation just isn’t flowing.
That is why I am here to try to help! Here are 20 questions to help you ditch the dead-end conversations.
1. What are your top three favorite things to talk about?
I wouldn’t start out with this question, but I would definitely put it at the forefront of the conversation. If you ask, “What is your major or job?” this question would be good for follow-up.
2. What do you like to do in your free time?
If you don’t add in the “free time,” then most people will say work. This allows for the opportunity to get to know possible interests that may be similar between you two.
3. What would you do with $10 right now?
I had a guy ask me this question, and it made me think a lot harder than the typical “What would you do if you won the lottery?” or “What would you do with a million dollars?” questions.
4. What are your top three favorite movies?
This is just another way to get to know someone’s interests. I, personally, love movies about football, cars or cheesy romantic couples, and some of my interests are football and racing.
5. What is your favorite adventure you’ve been on?
This one is pretty self-explanatory. Instead of asking about their traveling experience (which is really broad), you can ask about a specific adventure.
6. Who is the most interesting and/or accomplished person you’ve met?
Sometimes it is really sweet to see the answer to this one. Some people will answer with a famous person, but I had a guy answer his mom, and that just about melted my heart.
7. What are you most known for in your friend group?
This is an interesting one to ask because I have never gotten the same answer. This question also usually leads to funny stories.
8. Is there something you’ve done that you think everyone should try at least once?
I once had a guy tell me that everybody should go to an NFL game at least once in their lifetime. Needless to say, we bonded over football for the next 20 minutes.
9. What is something that you are always down to do?
This one has such a wide range of answers. I’ve gotten completely innocent answers to Rated- R answers. I think this is one of my favorite questions to ask on a first date or even a new Tinder match.
10. Who inspires you and pushes you to do your best in life?
This is a question that can be answered in one word if the other person is bad at conversation. Therefore, if you ask this question with someone who isn’t well-versed in conversation etiquette, then be prepared to ask why or throw out another one of these questions.
11. What country would you never want to travel to?
Most people talk about where they do want to travel, but I think it is interesting to turn the tables every once in a while.
12. What is your favorite family tradition?
This can be hard to answer, especially if the person you’re talking to has had a rough upbringing. If you are willing to possibly get into a sad or heavy discussion, then you’ll be okay asking this one.
13. What is your most embarrassing memory?
I love asking this question as an ice breaker. It always leads to interesting stories and both of us laughing.
14. What is the strangest way you have become friends with someone?
Every once in a while, people don’t have an answer for this one off the top of their head, but I definitely think it is a fun one to ask.
15. Are there any little things that can make your day significantly better?
Okay, so maybe this is my favorite question to answer for myself, but I like asking it to my dates because I can see their eyes light up when they talk about the things they love.
16. Who, other than your parents, have you learned the most from in life?
This one can pull at some heartstrings, so be prepared for a potentially deep conversation. Although, I think deep conversations are the best way to go.
17. Is there a slogan or saying that your friends associate with you?
You could also word this question as “What is something you say a lot?” An example for me would be “No pain, no gain” because I say it all the time.
18. What is your limit on social interaction?
This is a compatibility question. If you are a complete introvert but your date is a complete extrovert, then that may be problematic if you are searching for a relationship. However, if you are both introverts or both extroverts, then it may be a good sign.
19. When do you feel most out of place?
I like this question because it allows me to get a feel for the person’s personality, and it goes deeper than question #18.
20. What is the last new thing you’ve tried?
Once again, I have received a variety of answers to this question, so be prepared in case your date doesn’t have a filter.
In the end, chemistry will determine whether or not there will be a second date. Even if you have an amazing conversation, the chemistry might not be there. My advice is to just have fun and don’t put too much pressure on the situation. If it is the right person, the conversation will flow easily. Good luck on your pursuit of love!