Interesting Conversation Starters For Lesbian Singles

Lesbian Dating

15 Fun & Interesting Conversation Starters for Lesbian Singles on a Date

Pamela Gort

Written by: Pamela Gort

Pamela Gort

After two long-term relationships and five years of dating, Pamela Gort, The Lesbian Love Coach, spent years synthesizing the most effective and relevant dating and relationship practices into five easy steps called “Find Her and Keep Her" specifically tailored for lesbians. Using her warm, funny, direct coaching style, Pamela guides single lesbians to fall in love with themselves so they can attract and keep conscious, lasting, and loving relationships.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Conversation starters are crucial for any good date. They help you break the ice and get to know your date better. 

It can be hard to know what to say on the first date especially when you’re not sure how open your date is. We have all been on a first date with someone we really like. You know you need to ask some questions or risk being labeled as a conversational black hole. With these 15 conversation starters for lesbians on a date, you’ll be able to find something to chat about! Listen with strong curiosity, not only to ensure that her interests match yours, but to learn more about her. Find something intriguing about her answers — even if you have a different opinion. 

These questions will help build rapport, decrease your feeling awkward, and increase your chances of having an enjoyable time. Most importantly, they show you have a genuine interest in your date and in getting to know her more than just on a superficial level.

Note: Choose a few of these questions to generate interesting conversation. Mix up the fun questions with a more serious one. They are not in any order.

1. Tell me about where you grew up. Any favorite memories?

This question will provide relevant insights into her childhood, whether it was happy or difficult. She may have had some trauma. Did she work on it or is it still haunting her?  It is critical to learn something about how a person grew up to see whether she is well adjusted or has had some issues to deal with over the course of her life. You will be able to tell if she is proactive, willing to address issues or if she is still living as a victim of childhood circumstances. 

Photo of two women
You can discover things about her by talking about her childhood memories.

You will also learn what was important to her growing up such as family, friends, activities, community, school.  Did she have close friends or was she a loner? Did she have a good relationship with her parents and her siblings? Is she still close with them? Did she enjoy school? Did she spend time playing and having fun?  Did she grow up in the same house and town or did she move frequently? You can learn a lot by simply listening to what she shares with you and asking additional questions to go deeper.

During your conversation about the past, you may find out she had a bad childhood and is still reeling from the traumatic events. That need not be a conversation ender. Let’s be clear, you are not just looking for ways to rule her out, you are also looking for ways to fall in love with her and how she looks at life. Someone with a bad childhood could be a great partner if it is no longer haunting and triggering her.

2. What’s the best part of your job?

This question will evaluate your date’s interest in what she does for work. She will let you know whether she values her career, or it is just a means to live. If you are a professional committed to your career, you may also want someone who places importance on their career. You can ascertain quickly by how she answers this question if work is important to her. If she says the best part of my day is “when I leave work at the end of the day”, then she probably is not in love with her job. If she talks about challenging projects and getting recognized for her work, then she is likely serious about her career.

On the other hand, you may be looking for someone for whom work is not a priority. You’re hoping they have outside interests to keep them excited about life. Their answer will clue you in on whether they value life balance.

3. What have been some of your favorite vacations?

This question will divulge how much your date enjoys travel and what kind of traveler she is. If you love to travel to exotic places, you’ll want to date a woman who does that already or is willing and able to do it with you. How great would it be to find someone who has a similar list of places she wants to travel to? You’ll learn if she’s into adventure, culture, touring, volunteering, or playing it by ear. 

As a follow up, ask her what her favorite part of her experience was or why she enjoyed it so much. The cool part of the follow-up question is that she may learn some things about herself that she might not have realized before. Most people do not ask these deeper questions. They are not difficult, but they do make us think and feel — and that is the best part of meeting a new woman.

4. What were the last three movies you watched, and would you recommend them?

Our taste in the programming we stream can inform our likes and dislikes. Does she primarily enjoy comedy, romance, horror, drama, documentary and so forth.  Why don’t we like a certain genre of film? Do we watch movies to distract, educate or entertain? Are we one- or multidimensional in our interests?  Listen closely to her reasons for recommending them because this clues you in to her values. 

5. Which movie has been the most influential to you in some way (for better or worse) and why?

I love this question because it forces her to think of one movie and that movie shows what turns this girl’s head, what makes her tick, what impacts her. Let her explain why and she will reveal so much about her values and her desires. Ask her to share some favorite scenes from the movie. Imagine how excited and valued she will feel when she gushes about her favorite movies with you. 

6. What’s your favorite way to spend a Saturday morning?

If you want to know what she enjoys in her free time, this question will give you the answer. Often people will write things in their profile that make them look good. Who will admit they are lazy or inactive? No one, I hope. If she tells you she sleeps until noon and then watches hours of TV, you can bet she’s not going to be very active.

Photo of women on a train
It’s important that couples share similar favorite hobbies and activities.

Now, if she’s a nurse or doctor who works 12-hour shifts, then being lazy on her day off is totally understandable. If you are looking for someone who will go hiking or do a 40-mile bike ride, then you can check her off your list. Let her tell you what her days off are like, and you will have a peek into her activity level preference.

7. What is your favorite type of animal and why?

The animals we love and have as pets say a lot about us. Are you a cat or dog person or do you love both? Could you be a cat person and get along with a dog person? Only you know the answer. The way she answers this question will reveal her reasons for why she loves this animal.

8. What’s the best thing about living in your city?

If you live in different cities, this question provides an opportunity for you to discover a new place through someone else’s eyes. Learning about where your date lives can help identify her interests and the activities she likes. Does she frequent the beach, lake, parks, hiking trails, museums, concerts, farmers markets, restaurants, bars? Are these things you like too? 

9. If you could have any superpower what would it be and why?

I love this question because it reveals what sense or skill or talent she finds important and that she would want to supersize. Is it a power that works for good or not so good? Again, this comes down to a question of what she values and how creative she is, and it may even show her sense of humor. 

10. What was the last thing you binge watched on Netflix?

I would want to know what kind of programming captivates her interest so much that she would binge watch it. Is she waiting for another season or did it end the way she thought, the way she wanted? Would she have created another ending instead? Maybe she’d want to watch the series again with you some time!

11. How often do you do yoga or meditate? 

If you are a yoga and meditation devotee, ask this to see if she dabbles or if this is a real practice. You can be a devotee but have a girlfriend who is not. If you really want her to also be a devotee, then the answer to this is quite important to you. If being in your body and being present is important, then these practices will also be important.

12. Do you make a deliberate effort to star gaze or look at the moon or watch sunsets?

The moon, sun, and stars are romantic elements that often reveal a deeper spiritual sense of a person. Most people love sunsets, but have they thought about why? Is it the colors, the uniqueness of each one, the surprise at the end of the day or something else? Ask her what she enjoys about stargazing or sunsets and listen to her answer. 

13. What makes you feel in awe?

This is one of my favorite questions. Not everyone will understand at first. The internet dictionary definition of “awe” is a feeling of reverential respect mixed with fear or wonder.  I choose to use the positive not the fear-based definition. To wonder about the world and to be in awe is a blessing. Are you in awe of nature, people, mothers, the human body, the will to live, your dog or cat, your heartbeat, a gentle breeze? What is it that creates a sense of awe for you? 

14. What is the best thing to you about being a lesbian? When and how did you come out?

This open-ended question will divulge many different responses. There are no wrong or right answers. There are just so many beautiful, insightful stories about lesbian or bisexual women coming out of the closet. Be prepared to hear them and learn about yourself in the process. 

Photo of two women smiling
Lesbian women can bond by talking about their experiences coming out.

Getting to know how she came out is just an extra piece of information. It will reveal how accepting her family is and how secure she is in her own sexuality. She may still have some lingering unease or be powerfully out and proud today. Many lesbians will not date someone who is still in the closet with work or family. Today most lesbians are out but may have gone through a tough time being accepted. 

15. What do you think of the Lesbian U-Haul 2nd Date Joke? Was it ever true for you? 

Lesbians are known for jumping into relationships too fast. Lesbians seem to have that nesting instinct. As soon as they have sex, some of them often think “this is it”, “she’s the one” and for the next three to six months, they are in limerence — or obsessive infatuation as one dictionary definition explains it .  I think many of us are guilty of this especially early on. I know I was! Attraction hormones and neurotransmitters, dopamine, and oxytocin are raging! Let her share her experience and then share yours.

Remember: Being Interested in Others Makes You More Interesting

Meeting new people can be a bit intimidating, but it doesn’t have to be. To make the process less stressful and more enjoyable for everyone involved, I recommend asking questions that build rapport and show you are interested in getting to know your date better. It’s important to ask good questions that won’t turn the date into an interview or interrogation. Help your date relax and be open about herself and feel heard. 

Getting answers to these questions serves two purposes: 1) It will help you decide who she is and if she fits who you are looking for: and 2) more importantly, these questions will make her feel heard and valued. Most people don’t ask these questions so you will create an experience for her as you listen intently with the goal to understand who she is on a deeper level. 

Ask questions that spark deeper conversation rather than ones with pat answers or obvious responses. You may not want to go this deep with all your dates, but if you do, you may very well find yourself making friends quickly and enjoyably. The most important key is to listen and learn about your date. She will tell you what you need to hear to decide if she has the right stuff to take this relationship further. Use these questions as a guideline for what to talk about on a first date but don’t forget to think outside the box!

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