Dating a New Squeeze – Convo Starters

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Alan Schin
Updated on November 13, 2025 | 20 min read
Dating a New Squeeze – Convo Starters

You’ve met a girl, either in person or online, she has sparked an interest, and you’re ready for that first date. You’ve had some initial small talk, but small talk is nowhere near meaningful conversations – interesting conversations that let you both decide if there if there is genuine interest and should be dates beyond that first date.

Now, the next challenge – what to talk about on a date with a girl you have only just met, especially on that first date and onto a second date and beyond in this early stage of a relationship. In fact, the conversations you have on that first date should give both of you an idea whether a second date should even happen.

For those who want to have engaging conversation, avoid awkward silences, and keep the conversation flowing, some planning ahead would be a good idea. And it’s an absolute must for those of you who have a tough time starting conversations or keeping conversation flowing.

Pre-Planning

Pre-planning may seem kinda dry, unromantic, and contrary to the spontaneity that should be a part of dating someone. But stick with us, and you’ll understand why it’s important.

Deciding on Appropriate Conversation Topics for a First Date

Obviously, you’re not going to jump in asking questions about her sex life or other deeper topics like personal challenges and mental health. Religion and politics might also be subjects too deep for a first date unless these could be dealbreakers for you. Then, yes, ask those questions so that if there isn’t some common ground on these, you won’t waste her time or yours on any future dates. She may have dealbreakers too, so if she asks you some of these types of questions, be honest.

What, Where, and When?

People in the LGBTQIA+ community tend to be less trustful of those they have just met, and that includes lesbians of course. They should be especially cautious when meeting up with someone in person for the first date, even more so if they have met in a chat room, on social media, or even dating websites that don’t screen their users well. If you have met through a mutual friend, no problem.

The two of you need to decide on what this first date will be. If it’s a concert or a noisy club, there won’t be an environment for conversation, unless you make plans to go someplace much quieter later on.

If you decide to meet up in a public place during the daytime, say a coffee shop or a quiet restaurant with plenty of space for private conversation, that’s perfect for plenty of talk.

If you date is online, deciding all of this is much easier. For one thing, you date can (and should) happen via video chat, so that you can observe her body language as she talks. And if you want it to be more like a real date, you can both watch the same movie, TV show, or concert, and talking about it afterward will be a comfortable opening for your conversation.

As you are now settled on the what, where, and when, it’s time to speak to topics – which are appropriate conversations starts for a first date, and which are not. And within those topics are sample questions and even follow up questions that are more open-ended and likely to keep both you and your first date genuinely interested.

Appropriate Topics for First Date Conversations

A first date should be used for lighthearted conversation but not superficial stuff. The point of these early conversations is for both of you, even though keeping conversation light, will learn enough about each other to see if there is enough compatibility and common interests to be worth moving forward or, if not, moving on. And there are plenty of things to talk about without deep discussions of hugely intimate and personal topics that should come much further down the road in a relationship.

So, let’s have a look-see at what appropriate conversation topics are and what you can learn from them by posing questions in a creative way that will keep the conversation flowing with a potential partner and provide new insights.

Job/Career

“What do you do for a living?” If you want a conversation to stall, this is just the question to ask. Once she has told you what she does and maybe described it a bit, and you have done the same, what next? Instead, ask more open-ended questions that will bring out what she does for a living and keep the conversation going. Here are some examples of those types of questions:

  • What’s the most favorite and least favorite thing about your job?
  • When did you decide that this line of work was for you?
  • Was there someone in your life who inspired you to go into this line of work?
  • How do you achieve work-life balance?
  • What’s your idea of a dream job?

You’ve now turned what could be a dead-end question into an interesting topic that anyone will feel comfortable talking about. And in the process, you have learned more about her than just her job.

Now, here is something else you should watch for – it’s important. While you have this conversation, or any conversation about any other of these topics, does she show as much interest in what you are saying as you do when she talks? Or does she always manage to bring the conversation back to herself. This can be a cue that she is pretty self-centered. If it becomes a pattern, it’s not a good personality trait.

Travel

Here’s a chance for some good talking points on that first date that can keep the conversation lively.

“Do you like to travel?” Pretty meh. Put some spark into first date conversations with these:

  • What’s the best trip you’ve ever had?
  • If money were no object, what are your three top dream destinations?
  • Do you have any funny or horrible travel stories?
  • If you had a staycation within a 25-mile radius of your home, what would you do?
  • If you were transported to a new city, where would you go first?

Her answers will not only let you see if your travel delights jibe, but you’ll get a feel for her vibe too, like does you prefer outdoors adventures or a nice resort with all of the amenities.

Hobbies, Interests, Spare Time, Talents

There is so much to unpack here, and these first date conversation starters could take up the entire first date and roll into a second date and beyond. So, maybe don’t ask all of these questions on a first date because you want to hit other topics too. Choose from among the following open-ended questions – maybe those that you are most curious about:

  • What do you do in your free time?
  • Do you have one hobby that is your favorite? How did you get into it?
  • Do you have a favorite cause? How do you support it?
  • How do you stay active?
  • Do you have a special or odd talent that not everyone knows about?
  • How do you spend an average weekend?
  • Do you prefer to pursue your hobbies and interests by yourself or with others?
  • What’s a hobby that is not currently one of yours but that you would like to get into?
  • What do you consider to be your strong talents?
  • Do you follow current events? What’s your source for information?

While these are not necessarily exciting conversation starters, they can provide some good insights into this woman, even reveal some of her values. Does she support causes that do good for others? What are her political leanings? Is she more of a “solo” or a “group” person?

Books, Movies, TV, Music

This category too can reveal a lot about your first date’s personality, so pay attention to her responses to see if there is compatibility. But don’t despair if there isn’t any common ground here. Opposites do attract, and maybe you both would be willing to experience each other’s tastes here.

What’s the last book you read just for pleasure? What did you like about it?

Do you like fiction, nonfiction, or both? What types of fiction do you like? Nonfiction?

What’s a movie you have watched many times and will never tire of? What’s the draw?

What types of movies do you prefer?

Have you ever binge-watched a TV series that is no longer on or a Netflix series? What are your favorites?

What are your favorite TV shows that are currently running?

If you had your choice of any concert to go to, what would it be?

Are there any older music groups that you still listen to?

What are the top songs on your playlist?

Is there a favorite song that always makes you want to dance? Do you play it while you are doing household chores?

You can learn a lot about a person via these questions. Their preference in books, for example, may reveal whether they are a realist, idealist, romantic, etc. The same goes for movies. If they adore Stephen King novels and movies, they like horror fantasy and want to be frightened. Likewise, if they prefer romcoms and happy endings, they are romantics. If they like historical fiction or nonfiction, they are realists who want works that feed their intellect.

Now, if you don’t share the same tastes, no problem. You can suggest that you each pick a favorite movie to watch on subsequent dates.

Childhood, Family Members, and Friends

This may be a tricky topic to talk about, because not all people fall into the same methods and patterns of growing up. As you delve into this area, be mindful of watching the nonverbal cues that your first date may be giving off. If she looks down, for example, the topic is clearly uncomfortable, and you need to quickly change the subject and keep the conversation going without an awkward silence. We all have past experiences that are painful, and do not want to share details of them with others. Honor and respect that.

Here are some open-ended questions to ask about that are good conversation starters for a first date and beyond talk. And of course you will share yours as well. Most of these will let your talk flow naturally, but remember, as soon as the conversation feels uncomfortable, cut it off.

  • What’s your favorite childhood memory?
  • What was the best family vacation you went on as a kid?
  • When you were a kid, what did you dream of being?
  • Who were your heroes when you were young? Are any of them still your heroes?
  • What’s the best piece of advice you ever got from a family member? The worst?
  • Which member of your family are you closest to? What makes them your favorite?
  • How old were you when you first set some life goals? What were they and are any of them still your goals? Have you achieved any of them?
  • What qualities does your best friend have that endear you to them?
  • What kinds of things do you and your best friend do together?
  • What is the dumbest or riskiest thing you did as a teenager?
  • What’s the best course you ever had in school? What made it so special – the teacher? the course subject? Is there a teacher who had a profound impact on your own life? There’s a lot to talk about here, which is a good thing.

Lifestyle

There are so many topics within this category, that you will have no lack of conversation starters on your first date. Remember, though, that your date should not begin to look like an interrogation, so, if you both still feel a connection, you will have plenty of dates to cover all of the sub-topics. Choose those that you really want to talk about for the first couple of dates – those that will reveal more about this person’s values and preferences. Many of them will just flow naturally during normal talking

  • What does you normal weekend look like? (If you know they work on weekends, change the wording to days off). Here, you’ll get an idea of their schedules and routines and whether they involve lots of partying and going out or if some of their free time is spent relaxing and unwinding.
  • Do you like alone time? If so, how do you spend it? If they spend it binge watching, that’s fine. But if they spend it reading or pursuing one of their hobbies, then it indicates a higher emotional intelligence – and they tend to be more self-aware.
  • Are you an early bird or a night owl? If an early bird, what do you do when you get up in the morning? If you’re a night person, what are your favorite things to do? Her responses will give you more insight into her priorities.
  • Do you have a bucket list? What are the top three things on it and why did you choose them? (This makes for a good conversation about life goals and future plans). Share your bucket list too. Your date’s answer and yours may not be the same things, but there might be general similarities such as travel or early retirement, and talk about those general similarities
  • How has your experience with online dating been? Obviously, this is a natural question to ask if you two have met on a dating site. If not, ask her if she has ever used one. If she has, let her talk about that experience, and pay close attention to her responses. If she spends most of her response bashing the people she has been matched with, using comments like “I can’t believe how many idiots there are in this world,” proceed with caution. Look for comments like “I’ve met some interesting women and had some good conversations but some duds too.” When you get only negativity, that says a lot about her character.
  • How much time would you say you spend on social media in a day? (Note: the average American spend just under 4.5 hours a day on this activity). She may fudge on this, so she doesn’t seem to be a social media junkie, but make sure to ask her what her favorite platforms are and why. The conversation can flow into what you both find most entertaining, what kinds of posts you create, and talk about some of the funniest or worst posts you have seen.
  • If you could have three people for dinner, dead or alive, who would you choose? Her response could give you some insight into her values. She may choose famous historical figures, members of family who have passed, or current celebrities. If she chooses Will Smith and Chris Rock, she definitely has a sense of humor or thinks she can play peacemaker.

Sometimes, it’s fun just to play something like 20 questions. So, introduce the game. You get to ask her 20 questions that have short answers, and then she can do the same. Here are examples of these types of questions:

  • What one word would your friends use to describe you?
  • If you were to write a novel about your own life, what would be the title?
  • What one song describes your life right now?
  • What’s a crazy fashion trend you once took on?
  • What’s your favorite meal?
  • What’s your favorite restaurant or favorite restaurant type?
  • best meal you ever cooked
  • In a short phrase, what is the most important thing you have learned from past relationships?

Another variation of this game is called “this or that.” It’s fun but takes a bit more prepping. Fortunately, the web is full of “this or that” questions for couples, so you can go through them and pick the ones that you like the most. These are rapid fire questions calling for quick answers. Here are a few examples:

  • dog or cat person
  • introvert or extrovert
  • cook at home or carryout
  • city life or country life
  • optimist or realist
  • save or spend

Money and Finances

This is a rather short topic and can be put to bed pretty quickly. There are a few questions that will give you some insights into her priorities and values.

  • When you get a surprise windfall of cash, let’s say an inheritance, what do you do with the money? Look for a response that shows some balance. If she talks about a spending spree with some of it, saving or investing with a big chunk of it, and maybe donating some to a favorite cause, your date likes to set priorities and stick to them. It’s a good sign.
  • If you were a multi-millionaire, what would you do with all that money? Again, you’ll get some insight into her priorities and values. She might say things like take early retirement and build her dream home in a place she has always loved; she might talk about setting up a scholarship foundation for needy students; she might make a huge donation to her favorite charity. Again, you are looking for a balance between satisfying her own wants and the needs of others.
  • Do you believe in having a tight budget, a flexible one, or living by the adage that “budgets are for wimps?” Look for a middle-of-the-road answer here, maybe that she does set a budget but is flexible enough to modify it when needed.

Wrapping it All Up

This guide is a lot to take in for sure. It’s filled with conversation starters that will let you probe your date’s likes, dislikes, approaches to life and love, and dig into principles and values that make her tick. Just remember this: if you like what you find out at first, you have plenty of follow-up dates to learn more and more. Take your time, let the topics flow naturally into your conversations, and have some fun while you do this.

The Answer to Finding the Best Romantic Fit? Taimi

If you’ve tried online dating services in the past without much luck, you haven’t tried Taimi. If you are looking for the perfect lesbian partner for whatever type of relationship you want, then Taimi is your “go-to” place.

What is Taimi?

First, this dating app is the largest in the world that is exclusively for the LGBTQIA+ population – 29+ million to be more specific. And among that number, there are literally hundreds of thousands of lesbians looking for the same type of relationship. Within that huge number are are plenty in your locale – plenty that you probably would never meet otherwise using “old school” methods – friends who set you up, hitting gay clubs and bars, sketchy chat rooms, and such.

Taimi Features

To get the full picture of what this app offers, access the Taimi website and check out the general information and then the sections specific to lesbian dating. Here’s just a few of the features:

  • Joining is easy via the app download on both app stores – it’s free
  • Help with creation of a stunning profile that will capture interest of like-minded lesbians
  • Upload great action pics to go along with your profile
  • In-house state-of-the-art matching system that includes AI to continually refine matches
  • Multiple ways to communicate with mutual matches, including video chats, and fully private convos that include photo sharing
  • Option to set up a geolocation radius to ensure matches are in your locale
  • Hundreds of icebreaker questions to get conversations going
  • Responsive customer service

Much More Than a Dating App

Taimi has built a community among all of its users that honors, respects, and celebrates every member – who they are, who they love, and the type of relationship they want. To do this, Taimi offers the following:

  • A social media platform composed of lots of groups to join to discuss issues and challenges and just to have fun posting and responding to the posts of others. And any member is free to start their own group, promote it, and gain a following.
  • Games, contests and other activities throughout the year that bring the entire community together to play. The old adage, “people who play together stay together” is the idea.
  • A safe and secure environment based on strict community standards and identity requirements for those who might be posers.

Give Taimi a try – you’ll love everything about it.

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Alan Schin

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