Second-Date Conversations To Hold Their Interest

Updated August 11, 2023by Regain Editorial Team

The first few dates can be the trickiest part of a new relationship. You’re still learning about each other, and a deeper connection is only in its earliest stages for most people. The spark of potential is there for both of you, and all that’s left is to discover whether you’re compatible beyond the surface.

Are You Worried About What To Say On A Second Date?

The best way to do that is through conversation on your first few dates. Read on to learn about topics you can use on your second date to hold their interest and discover more about your potential partner and how therapy can teach you communication skills to make expressing your needs and emotions easier. 

The Importance Of Conversation On The First Few Dates

The first few dates give you a glimpse into who someone is and what it would be like to have them in your life. You’re both learning about each other and deciding whether you want to spend more time together. First dates are usually about first impressions and choosing to pursue a shared interest. The second date generally offers a chance to learn more about each other in a lighthearted way while experimenting if the mutual attraction grows. You can start initiating deeper conversations on the third date to begin building an emotional intimacy connection.

“Cohen's findings indicated that women were more likely than men to use early behavior and verbal communication to gauge the level of perceived attraction from their date. Men, on the other hand, did not view these behaviors as indicating that their date was less attracted to them.” — Research about early dating conversation habits, Psychology Today

Going Beyond A First Impression

Whether you met through a dating app or in person, the second date is your chance to go beyond a first impression and create a pleasant memory with your companion. Focus on back-and-forth conversations that allow both people to feel heard and understood. Show that you're listening by asking relevant questions that help facilitate the conversational flow while allowing you to learn about your date. 

How To Keep The Conversation Flowing On The Second Date

You made enough of an impression on your first encounter to secure a second date, but what do you talk about now? Try some of these topics and strategies to keep a lighthearted conversational flow that helps you learn about your date and makes them feel like the focus of your attention. 

Show An Interest In Their Passions And Personality

The second date is a perfect opportunity to learn more about your companion and discover facts about their personality that draw you in further. Ask them to tell you about something they love passionately, and watch them light up with excitement as they talk. Learn their favorite personality trait or what habits are instant dealbreakers for them. 

Ask About Their Future Hopes And Dreams

Discussing future goals, ambitions, and dreams can be a fun, lighthearted way to learn more about their desires. You can ask what they would do if they could make any life change with no financial concerns or the first thing they would buy after winning the lottery. 

Keep The Conversation Going With Open-Ended Questions

Remember that you’re responsible for half the conversation, and questions that only require yes or no answers don’t give your date much room to respond. Help keep the conversation going by asking open-ended questions that give your date something to respond to and often lead the discussion in new directions. 


Questions To Ask On A Second Date

Remember that the conversation goes both ways, so don’t just interrogate your date. Share your answers, too. 

  • What did you like most about me on our first date? Is there anything that causes concern you’d like to ask about?
  • Who in your personal life do you admire most and why?
  • What’s one mistake you’d never make again?
  • How do you feel about your work? Do you enjoy what you do?
  • What is one of your greatest fears?
  • What is your most relaxing self-care strategy?
  • What are your biggest dreams?
  • What’s your most humorous first-date experience?
  • What is your favorite thing about this city?
  • Do you have any pets, and can I see pictures?
  • What would you grab if your house was on fire and no living creature was in danger?
  • Can you describe your personality in three words?
  • Do you have unique or quirky habits or hobbies?
  • What role would you play in an apocalypse?
  • What traits do you find most attractive in a partner?
  • What did you want to be when you were ten, and how does it compare to what you do now?

Leave Your Phone Put Away And Focus On Them

Unless you're likely to be needed for an emergency or on call for work, keep your phone put away during your date and direct that attention toward your companion. You’re far more likely to get a third date if they feel like you focused your energy and attention on them during your time together. 

Learn About Each Other’s Favorites, But Make It Fun

Bypass the mundane “What’s your favorite…” questions and turn them into a game. The goal is to guess things you may have in common, and the first person to make the other say, "Oh, me too!" five times chooses the next date. You’ll learn fun facts about each other, and it provides the perfect opportunity to negotiate a third outing. 

Getty/Vadym Pastukh
Are You Worried About What To Say On A Second Date?

Discuss Your Childhood Experiences

Childhood experiences can lead to mixed responses, so you may want to save this conversation for when you're more comfortable with each other because everyone didn't have positive early years. Try bringing up a childhood experience and gauging their response to the topic before proceeding. 

Don’t Just Wait for Your Turn To Talk—Actively Listen 

Some dates can feel like your companion only wants to talk about themselves and is just waiting for you to finish speaking so they can talk again. Show your date that you’re actively listening. Respond to how they answer your questions with their words and body language. Steer away from topics that make them uncomfortable and focus on uncomplicated ways to learn more about each other. You may earn bonus points if they mentioned something during the first date that you can ask about when you meet up again. 

Helpful Tips For Your Second Date

Try some of these tips to help your second date go smoothly as you work to build an emotional connection and show them the spark of potential can become something more. 

Get Moving And Do Something Fun…

Doing something physical and fun together, such as hiking, having a picnic, exploring an event side by side, or even taking your pets to the dog park, can provide a way to create exciting memories of your second date. 

…But Leave Space For Conversation

However, you want to ensure you allow opportunities for conversation. If you’re too busy to talk, you may both have fun, but you won’t make much progress getting to know each other. 

Should You Kiss Them?

If you didn't end the first date with a kiss, you might want to consider kissing them goodnight if things seem to be going well and you get the sense that the mutual attraction is continuing to grow. Pay attention to your date’s body language, and if they back away when you lean in for a kiss, respect their wishes. 

How Therapy Can Help You Build Communication Skills

Many people struggle to effectively communicate their needs and emotions to their partners and people close to them. Consider working with a licensed therapist online through a virtual therapy platform focused on relationship issues like Regain. Therapy can help you find healthy ways to set and explain boundaries, manage conflicts, and express feelings to your dates and eventual partners. Parents or guardians seeking online treatment for children ages 12 to 19 can contact TeenCounseling for assistance in supporting their children through the turbulent teen dating years. 

“Sessions with Natalie are very insightful and give practical advice on implementing new habits and changes. Be prepared to engage and be challenged to think in a different way. I know that my partner and I can already see improvements in our relationship and feel more positive about working through our issues together.”

“Austa has been wonderful thus far. She has helped my partner and I during an unimaginably difficult time... She has also guided us in communicating effectively and setting appropriate boundaries in our relationship. I was hesitant to pursue counseling at the beginning, but I truly believe that it is making a difference for our relationship. Austa is easy to talk to and she is a great listener. I would wholeheartedly recommend her as a counselor.”

The past several years have inspired a colossal interest in versatile treatment options. Recent studies show that online therapy is as effective as traditional in-person treatments—often at lower costs with shorter wait times. Teletherapy platforms offer the added benefit of access to a much more comprehensive network of licensed mental healthcare professionals, making it far more likely that you’ll connect with a therapist who makes you feel comfortable and works well with your personality and therapeutic needs. 


The conversation can be one of the most crucial aspects of a second date, and it can help to prepare a few subjects before you get together. This article offers insight into helpful communication methods to help you through the second date and beyond, topics you can use to keep the conversation going, and how therapy can teach you valuable communication skills. 

For Additional Help & Support With Your Concerns

This website is owned and operated by BetterHelp, who receives all fees associated with the platform.
The information on this page is not intended to be a substitution for diagnosis, treatment, or informed professional advice. You should not take any action or avoid taking any action without consulting with a qualified mental health professional. For more information, please read our terms of use.
Get the support you need from one of our therapistsGet Started
This website is owned and operated by BetterHelp, who receives all fees associated with the platform.