dating advice

Top 5 Best First Date Tips For Men

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First Date

Namaskar, I’m sharing how to have a great first date. Today, I’m sharing five tips for a successful first date to ensure you leave feeling confident, regardless of the outcome. Follow these tips, and you won’t be thinking, “I could have done this better.” Let’s jump into it!

Tip 1: Dress Well for Your First Date

Number one on my list is to dress well. I’m not saying dress like someone you’re not or wear what you think she wants. If you buy an outfit just for the first date and don’t have similar clothes for a second date, she might notice you dressed to impress in a way that’s not your style. When I say dress well, I mean dress like the best version of yourself. This depends on the date setting:

  • For a casual brunch on the weekend, go for jeans, sneakers, and a nice shirt to fit the vibe.
  • For after-work drinks or dinner, maybe lean toward business casual.

I won’t get super specific about outfits since that’s a whole video on its own. If you want me to cover what to wear on a first date, let me know in the comments! Just dress for the setting—don’t try too hard with a full suit unless you’re hitting a gala, which I wouldn’t recommend for a first date anyway. Look like you put in effort, not like you rolled out of bed. If a guy shows up in a stretched-out V-neck looking hungover, it’s an instant turnoff. First impressions are key, so make a good one!

Tip 2: Pick the Perfect First Date Location

Next, pick the perfect place. This varies based on where you live and the season. In California, where it’s sunny and 75° year-round, you have more options than in Cleveland, where it’s cold seven months of the year and winter activities are limited. Choose a public setting where you can get to know each other without revealing too much too soon. I don’t recommend inviting her to your place on the first date—it shows all your cards and leaves no mystery.

Go somewhere casual and fun where you can talk one-on-one. A fancy dinner date isn’t ideal for a first date. If you realize 20 minutes in that you don’t click, you’re stuck in a four-course meal with someone you don’t like, and you’re footing the bill. Plus, flashing too much money might attract the wrong type of person. Avoid places like movies for a first date with someone you’ve never met. Sitting in silence for two hours sharing popcorn is awkward and kills any chance to connect. If you’re already friends, a movie’s fine, but for online matches, stick to conversation-friendly spots like a café or a relaxed restaurant.

Tip 3: Master First Date Conversation

Conversation is arguably the most important part of a first date. Get to know her—what she’s into, who she is—but she should be curious about you too. If she’s not asking you anything, it might mean she’s not interested, and that’s okay. Not every date will be a match. If you’ve checked her Instagram and know things you shouldn’t, don’t ask questions to seem impressive or robotic. Be candid, go with the flow, and notice what she lights up about. Focus on those topics and see if you share common interests.

Don’t talk about yourself the whole time—I’ve been on dates where the guy did this, and it’s awkward and unenjoyable. If you’re asking all the questions and getting nothing back, it’s a turnoff. Show curiosity if you’re interested. After the date, ask yourself: Do I want to know more about her? Are we compatible? Is a second date worth it? A good first date conversation in the right setting helps you figure this out.

Tip 4: Know When to End or Continue the Date

My next tip is knowing when to stop or continue the date. This is why a public place with a natural endpoint, like brunch, is ideal. When the bill’s paid and you’ve chatted a bit, decide: Do I want to keep going, or am I ready to call it? If you’re not feeling it or sense she’s done, be polite, say you had a nice time, and part ways. But if you’re both having fun, be spontaneous! Suggest something else, like a walk or a quick activity.

On my first date with Teddy, we clicked instantly at brunch. Neither of us wanted it to end, so he invited me to go shopping with him at an outdoor mall. We walked, talked, and I learned so much more about him in that relaxed setting. It was attractive that he thought on his feet and showed interest. Spontaneity can turn a good date into a great one, maybe even a full day that leads to years together!

Another thing: Pay the bill on the first date. I have traditional values, and I find it attractive when a guy takes initiative. It avoids awkward moments when the bill arrives. Teddy and I now split bills sometimes, but on the first date, grabbing the check is a confident move.

Tip 5: Be Clear About Next Steps

Finally, be clear about next steps. If you don’t want a second date, don’t say you do. Be polite, but don’t lead her on, especially if you’re both looking for something serious. If you’re unsure, don’t commit right away—go home, think it over, and decide later. Don’t seem too eager or overly available; it can set unrealistic expectations. But if you’re into her, let her know. At the end of my 12-hour date with Teddy, he said, “I’d love to see you again,” and it felt great knowing we were on the same page.

Now, the dreaded after-date text. As a girl, we overthink this—should I text him? Should I wait? Guys, if you had a great time, text her when you get home. Say, “Had a great time tonight, it was awesome meeting you!” It’s confident and stops her from stressing. Don’t rush to plan the next date, but if she responds with similar energy, you can suggest a second date later. For example: “Hey, had a great time today. I don’t know what your week looks like, but I’d love to see you again.” This shows interest without being pushy. Sincerity beats games when you’re looking for a quality connection.

Wrap-Up: Make Your First Date Unforgettable

That’s my list of five tips for a great first date! I hope you found this helpful. If you did, give it a thumbs up—I love connecting with you there and putting faces to the comments!

In the comments below, let me know:

  • What do you think of these first date tips?
  • Did I miss anything, or do you disagree?
  • Share your first date stories—mistakes you made or learned from. They’re fun and help us all grow!

Thank you so much for reading, and I’ll see you next time!

Tips for Texting, Single Dads, and Starting Conversations – Users Q&A

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Tips on Getting Back Into Dating as a Single Father

Namaskar, I asked my Instagram followers to ask me some questions, and I pulled some from there. I also answered some on my Instagram story, so if you missed it, it’s in my Instagram story Q&A highlight below with my answers. so if you want to participate, definitely submit DM through my Instagram. So, let’s get started! I am also active on twitter

1. What to Do If a Girl Doesn’t Answer Back for a Few Weeks?

I would say someone who really likes you is never busy enough to not talk to you for a couple of weeks unless they’re on a cruise ship and don’t have service. So, see things for what they are, like I say so many times, not what you want them to be. If someone is not responding to you for a couple weeks, 99.9% of the time it is because they are not into you. So, if you’re constantly putting in time and effort and energy and, you know, double texting this girl, messaging her all the time, and she’s only giving you responses every few weeks, I think it’s best to just move on. Because someone who likes you will want to talk to you, and you won’t have to pull teeth to get her to talk to you, right? She’ll just want to talk to you.

What to Do If a Girl Doesn’t Answer Back for a Few Weeks?

If you need to refer to my “She Likes You or She Doesn’t Like You” videos or “If Someone Likes You, You’ll Know” videos, those are all great videos on my channel to check out. But seriously, see things for what they are and not what you want them to be. You know deep down, most of the time, when someone does not like you or they do like you, and in this case, I would say she doesn’t like you and move on.

If someone doesn’t respond for weeks, they’re likely not interested. Move on instead of chasing. Someone who likes you will make time to talk.

2. Tips on Getting Back Into Dating as a Single Father

This is tough because I think, if I’m being totally honest, I think sometimes it does kind of shrink your dating pool a little bit because there are a lot of, you know, girls and guys out there who don’t want to date single parents, which I totally understand—it’s a personal preference. But I would say that it is important to be very honest about the fact that you’re a dad, and I think people who are willing to date single fathers would appreciate the fact that you are open and honest about that, and it would show that you obviously care about your child and want them to be a part of your life and dating experience.

I am obviously not a single parent, so I can’t speak from personal experience, but I have been friends with women who have dated single dads, and some of them had great experiences, others did not. I know some girls who have kind of taken on the role as a stepmom, and they are totally fine with that. So, don’t sell yourself short just because you’re a single father. There are plenty of girls out there that would have no problem dating a single father, same thing as girls out there who don’t care about height. I know there are people who do care, but for every person that does care, there’s someone who doesn’t.

My mom was a single mom and started dating my stepdad when I was very little, and I’m so thankful for the fact that he gave my mom a chance and, you know, dated her even though she had me because he has ended up being one of the best and most influential people in my life, and I really can’t picture what my life would be like without him. So, if you’re watching this and you’re hesitant to date single parents, I totally get it, but from a daughter of a single mother, I adore my stepdad, and I’m so thankful that he dated my mom, so keep that in mind too.


Being a single parent may limit your dating pool, but honesty about your role as a dad is key. Many appreciate openness, and there are plenty who embrace dating single fathers. Don’t underestimate your worth—some, like my stepdad, find joy in stepping into these roles.

3. What’s Your Favorite Date Night?

I am really not picky about date night. I think any date night is a fun night if you set aside special time for you and your partner. I personally like to go out to dinner and then come home and have just like a chill night, watch some movies, have some hot chocolate and popcorn, and just kind of have a little cozy night in. That’s kind of my favorite thing to do, but there are a million awesome date options.

4. Best Way to Start a Conversation With a Girl If You Have Anxiety

This one’s tough, and I have anxiety, and I’m an introvert, so I totally get it. I think the best thing you can do is kind of just shift your mindset about it. So, don’t go into it thinking, “I have to get this girl to like me,” or “Oh my gosh, she’s so pretty, she’s gonna think I’m stupid, I have to say the perfect thing.” Just talk to her like you would talk to any stranger, regardless of how attractive you think they are. Don’t put her up on a pedestal or think that she’s perfect because I guarantee you she has flaws. She’s insecure too. We all have things that we’re insecure about, so acting like she’s perfect or like you have to get her to like you right away is just going to stress you out and make you more anxious.

So, we want to alleviate that anxiety by, you know, just talking to her like you would any other person. I think the best way to start a conversation depends probably on where you’re at, but if you’re in public and you’ve never talked to her before, I think one of the best ways is to make it very natural and just ask her a question. Maybe you’re in line at a coffee shop, and you ask her, “Have you ever been here before? I don’t know if I should get the iced latte or the shaken espresso or whatever the heck it is, whatever you order.” Just ask her a question that’s very natural and gets her to start talking to you without just going up to her and being like, “I’m obsessed with you, you’re so hot.”

I guess it kind of depends on the situation you’re in too because if you were at like a nightclub or somewhere kind of sexy, it might be okay to go up and be a little bit more direct or to give a compliment. But if you’re just in a very natural setting, you want to make the conversation feel natural too. So, keep that in mind. I’ve done a video all about how to approach that I think would be really beneficial for you, so I’ll link that down below.

For introverts with anxiety, shift your mindset when approaching someone attractive. Don’t idolize them; treat them like any stranger. Start with a natural question based on the setting, like asking for a coffee recommendation, to ease anxiety and spark a conversation without pressure.

5. Why Do Girls Stay With a Guy Who Isn’t Good for Them?

I think a lot of girls have this mentality of “I can change him” or “he’ll be different with me.” Of course, talking about this on a lighter level is much different than talking about this on a deeper, like, more domestic abuse case. I’m not even going to get into that, but talking about it on a lighter level, maybe a girl that’s dating a bad boy that, you know, is cheating on her or whatever. I think a lot of girls, again, think that they can change guys, and we shouldn’t want to change people. We should want to date the person that’s right in front of us, and if you don’t want to date that person, you shouldn’t want to date their potential, right? See things for what they are, not what you want them to be.

FAQ: Your Dating Questions Answered

Q: What should I do if a girl doesn’t text back for weeks?
A: Someone who really likes you is never busy enough to not talk to you for a couple of weeks unless they’re on a cruise ship and don’t have service. If she’s not responding, 99.9% of the time, she’s not into you. Move on—someone who likes you will want to talk without you pulling teeth.

Q: How can a single father get back into dating?
A: Be honest about being a dad—it shows you care about your child. Some people don’t date single parents, but many don’t mind. Don’t sell yourself short; there are plenty of women who’d love to date a single father. My stepdad dated my single mom, and he’s been a huge blessing in my life.

Q: What’s a great date night idea?
A: I’m not picky—any date night is fun if it’s special time with your partner. I love going out to dinner, then having a cozy night in with movies, hot chocolate, and popcorn. There are a million awesome date options, so find what feels right for you.

Q: How do I talk to a girl if I’m anxious?
A: Shift your mindset—don’t put her on a pedestal or stress about saying the perfect thing. Talk to her like any stranger. In public, ask a natural question, like, “Have you been here before?” at a coffee shop. Keep it casual to ease your anxiety.

Q: Why do girls stay with guys who aren’t good for them?
A: Many girls think, “I can change him” or “he’ll be different with me.” We shouldn’t date someone’s potential—date the person in front of you. See things for what they are, not what you want them to be.

Is She Flirting with you? 8 Signs to Know for Sure

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Is She Flirting or Just Being Nice?

Hey guys, today we’re diving into one of the most confusing parts of dating for men: figuring out if a woman is flirting or just being friendly. Women can be warm, polite, and super engaging, which makes it hard to tell what’s going on. She’s laughing at your jokes, complimenting your shirt, leaning in when you talk, but then—bam—she mentions a guy she’s dating. So, how do you know if she’s into you? I’m breaking it down from a woman’s perspective with eight subtle signs to help you stop second-guessing and spot the difference between friendliness and flirting.

1. Her Energy Changes When You’re Around

When a woman’s flirting, you’ll notice a shift in her vibe that’s just for you. It’s not only what she says—it’s how she acts. Maybe she lights up when you walk in, her voice gets softer or more animated, or she smiles in a way that feels… intentional. She might touch her hair, adjust her clothes, or hold eye contact a little longer. For example, if she gets bubbly when you show up but stays the same with everyone else, that’s a flirty signal. If her demeanor’s warm but consistent across the board, she’s probably just being nice.

Quick Tip: Women flirt with their eyes more than you think. If she looks at you, then quickly looks away when you catch her, that’s a good sign.

2. She Keeps the Conversation Going

A woman who’s flirting will find ways to stay in touch, even if there’s no “reason.” She might send a random meme, reply to your Instagram story with a funny comment, or ask you something she could’ve Googled. These aren’t accidents—she’s opening the door for you to keep talking. If she’s consistently liking your posts, sending laughing emojis, or referencing little inside jokes, that’s digital flirting. But if she only responds when you reach out, replies politely, and lets the chat die, she’s likely just being friendly.

Heads-Up: Don’t read into someone just viewing your Instagram story. It means nothing unless she’s actively engaging with you.

3. She Matches Your Playful Vibe

Flirting’s like a game of ping-pong. If you’re playful or teasing and she throws it right back, she’s into it. Say you tease her about her coffee order, and she teases you about yours—that’s flirting. If she laughs but changes the subject or gets awkward, she’s probably just being polite. Texting’s another clue: if you send thoughtful messages and she responds with the same effort, she’s aligning with you. Short, dry texts when you’re being fun? That’s not flirting—it’s just a response.

4. She Makes Time for You

Everyone’s busy, but a woman who’s flirting will carve out time for you, even if it’s inconvenient. She might send a voice note on her commute, call after work, or suggest a quick coffee date. If she’s choosing to give you her attention, that’s a big deal. On the flip side, if she’s always canceling, rescheduling, or saying “maybe later,” she’s keeping you at a distance. When you do hang out, check the vibe: is she engaged or distracted? That tells you everything.

5. She Digs Deeper Than Small Talk

Polite chats are surface-level; flirting comes with curiosity. If she’s asking about your goals, values, or even past relationships, she’s trying to know the real you. If she remembers small stuff—like your favorite snack, your cat’s name, or a story you told weeks ago—that’s a major green flag. But if she sticks to basic questions, repeats the same ones, or doesn’t seem curious, she’s probably just keeping things friendly.

6. She’s a Little Nervous Around You

This one surprises guys, but nervousness can mean she’s flirting. If she laughs at your not-so-funny jokes, forgets what she’s saying, or gets flustered, it’s because she cares how she’s coming across. That vulnerability shows you’re having an effect. If she’s totally chill and casual, she might see you as a friend. Every woman’s different, but if there’s no emotional weight to your chats, it’s usually not romantic.

7. She Pulls You Into Her World

When a woman’s flirting—especially if she’s thinking long-term—she’ll start bringing you into her life. Maybe she invites you to a group hangout, introduces you to friends, or shares details about her day-to-day. She’s creating space for you in her world. If you’re always at arm’s length, only see her in passing, or never hear about her life, she’s setting friendly boundaries.

8. She Gives Back, Not Just Takes

Here’s a clear one: a woman who’s flirting doesn’t just accept your compliments—she reciprocates. If you say something nice and she responds with a flirty comment or compliment, she’s escalating the vibe. If she laughs off your compliment or changes the subject, she’s being polite and avoiding leading you on. Flirting’s a two-way street, so if she’s matching your energy, that’s the real deal.

Wrapping It Up

At the end of the day, flirting comes down to intention and effort. A woman who’s into you will drop cues through her body language, attention, and consistency. If you’re always wondering if she likes you, she might not be sending strong enough signals—and that’s your answer. But if she’s making time, playing off your energy, and staying connected, there’s a good chance she’s flirting. Trust the signs, not just your hopes.

What do you think? Have you noticed these signs before, or are there others I missed? Drop your thoughts in the comments—I’d love to hear your experiences! And if you found this helpful, stick around for more dating tips to level up your confidence.

FAQ: Flirting vs. Friendliness

Q: How do I know if her eye contact is flirty?
A: Flirty eye contact feels intentional—maybe she holds it a bit longer or looks away quickly when you catch her. If it’s just warm but the same as with others, it’s likely friendly. Check for other signs, like a shift in her energy.

Q: Does replying to my Instagram story mean she’s flirting?
A: Not always, but if she’s consistently replying with comments, emojis, or inside jokes, that’s a flirty move. Just viewing your story? Don’t overthink it—it’s not a signal on its own.

Q: What if she’s super nice but never texts first?
A: If she only responds when you reach out and doesn’t keep the chat going, she’s probably being friendly. Flirting involves her creating ways to connect, even if it’s subtle.

Q: Is teasing always flirting?
A: If she teases you back playfully and matches your vibe, it’s often flirting. If she laughs but dodges or seems uncomfortable, she’s likely just being polite.

Q: Why does she act shy around me?
A: Shyness or nervousness—like fidgeting or laughing too hard—can mean she’s flirting and cares about your impression. If she’s always relaxed and casual, she might see you as a friend.

20 Deep Conversation Starter Questions for a Great First Date

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20 Deep Conversation Starter Questions for a Great First Date

Namaskar, First dates can feel like a tightrope walk—exciting but a little nerve-wracking, especially when it comes to keeping the conversation going. You want to get to know your date without turning it into an interrogation room. These questions are all about digging deeper, finding common ground, and keeping things authentic, so you can see if there’s a real connection worth pursuing. Plus, I’ve added an FAQ at the end to tackle common first-date conversation worries.

Why These Questions Make a Difference

A first date isn’t just about filling the silence—it’s about learning who someone is, what they value, and if you vibe together. Courtney says asking the right questions can show you if you’re compatible in values, goals, and personality without making it feel like a job interview with cocktails. These 20 questions, taken directly from her videos, help you avoid awkward, one-word answers and get to stories, passions, and real talk that make a date memorable.

20 Deep Conversation Starter Questions

1. What Made You Interested in Going Out with Me?

This one’s a flirty way to start, asking what caught their eye—maybe something on your dating app profile or a moment you shared. Courtney says to ask it in a joking way, like “What made you swipe right?” It’s a fun, light question that shows what they’re into and can kick off a good conversation.

2. What Are You Looking for?

This gets straight to the point: are they after a casual fling or a serious relationship? Courtney’s big on believing their answer. If they say they just want a hookup and you’re looking for something long-term, don’t try to change their mind—it’s a time-saver to know early.

3. What Matters to You?

Instead of asking something narrow like “What are your hobbies?” this broad question lets them share what’s important—family, work, or maybe a passion project. Courtney says it’s a great way to learn their values without boxing them into a specific answer.

4. What Are You Most Passionate About at the Moment?

This is all about finding their “golden nugget”—that thing they light up talking about. Courtney loves this because it could be a new workout class, a TV show, or a side hustle, and it makes the conversation flow easily while showing you who they are.

5. When You Think of a Recent Big Political Event, Is There Something That Stands Out to You?

This question tests if they’re tuned into the world without going full-on political debate. Courtney says it can show if your views align and how much they care about what’s happening, which might matter to you.

6. What Does Your Work-Life Balance Look Like?

This digs into how they juggle work and personal life, which Courtney says hints at whether they can make time for a relationship. A softer way to ask might be, “What do you do when you get off work?” to see if they’re always working or prioritize downtime.

7. What Does Your Life Look Like 5 Years from Now?

This one’s about their big-picture goals—family, career, or travel. Courtney points out that if their vision (like no kids for 10 years) doesn’t match yours (wanting a family soon), you might not be compatible, and that’s okay.

8. What Would You Do If You Had a Week Off?

A fun way to learn what they love doing, this question shows if they’d travel, chill with their dog, or dive into a hobby. Courtney says it reveals their vibe and opens the door to more questions, keeping the chat lively.

9. When You Spend Time with People, How Often Are You the One Making Plans?

This shows if they take the lead or sit back in relationships. Courtney likes it because it reveals their communication style—planners might be reliable, while someone who never plans could leave you carrying the load.

10. How Well Do You Feel Like You Compromise with Others?

This can feel a bit like a job interview, but it’s about seeing if they’re flexible. Courtney suggests watching how they act—like if they insist on their choice of appetizer—or asking, “What’s a time you met someone halfway?” for a less formal vibe.

11. What Do You Think Is Important for a Healthy Relationship?

This gets them talking about values like communication or trust. Courtney warns that if they only mention something like sex, it might be a red flag if you’re after deeper connection. Watch their actions, too, not just their words.

12. How Do You Handle Conflict?

This tests if they’re self-aware about resolving disagreements. Courtney says it can feel buttoned-up, so you might try, “What do you do when you disagree with someone close?” If they say “I don’t know,” that’s a clue they might struggle with conflict.

13. What Is Something in Past Relationships You Needed to Work On?

This checks if they reflect on themselves. Courtney says if they blame their ex for everything, it’s a red flag. She suggests asking this on a second or third date so it doesn’t feel too heavy right away.

14. Who Is the Person You Talk to the Most?

A cute, light question that shows who they value—maybe their mom, best friend, or sibling. Courtney loves how it brings out stories and keeps things relaxed between deeper questions.

15. What Is the Best Gift You’ve Ever Received?

This fun one reveals what they cherish, like a thoughtful handmade gift or a fancy gadget. Courtney says it can lead to stories about their interests, like training for a race, and keeps the vibe easygoing.

16. What Was Your First Impression of Me?

Ask this when the date’s going well to see if they’ve been paying attention. Courtney suggests waiting for a second date to avoid awkwardness, but it’s flirty and shows how they see you.

17. What Made You Most Excited About Going on a Date with Me?

This is like the first question but focuses on what they were looking forward to. Courtney says it can lead to fun follow-ups like “What’s something totally random you’d like to know about me?” to keep things flowing.

18. What’s Something Totally Random You’d Like to Know About Me?

This playful question, straight from Courtney’s advice, brings out quirky facts or hidden talents. It’s a great way to add humor and balance out the deeper stuff.

19. What’s a Project You’re Working On That You’re Excited About?

Inspired by Courtney’s tip to dig into passions, this question gets them talking about something they’re into right now, like a creative project or a fitness goal, to spark an enthusiastic chat.

20. What’s Something You Do for Fun on the Weekends?

Courtney suggests asking about free time to see their lifestyle and interests. This question reveals what they enjoy outside work, like hiking or binge-watching a show, and helps you see if your vibes match.

How to Make These Questions Work

Courtney’s tips from her videos help you use these questions to keep things natural and engaging:

  • Prepare a Little Bit: Have a few questions in your head as a backup, but don’t script the whole date. Courtney says it’s like having a plan for an interview—just enough to feel at ease.
  • Ask the Right Questions: Go for open-ended ones that lead to stories, not one-word answers. Courtney says this makes the conversation snowball naturally into deeper topics.
  • Find Their Golden Nugget: Look for that thing they light up about and dive in. Courtney learned this from sorority recruitment—it makes them feel heard and keeps the chat effortless.
  • Tell Her About Yourself Too: Share your own experiences to make it a two-way conversation. Courtney says finding commonalities makes things more comfortable and natural.
  • Silence Is Normal: Don’t panic over brief pauses. Courtney says they’re okay and can even make the date feel more like you already know each other.
  • Be Authentic: Be yourself, not someone you think they want. Courtney says this helps you attract someone who likes the real you, making the connection genuine.

Why These Questions Are Great

These 20 questions come straight from Courtney’s videos, blending fun and depth to help you learn about your date’s values, passions, and lifestyle. They’re designed to avoid the interrogation feel, encourage storytelling, and show you if you’re a good match. Whether you’re digging into their dreams or laughing over a random fact, these questions set the stage for a date that feels real and leaves you both wanting more.

Wrapping It Up

First dates don’t have to be stressful. With these 20 conversation starters from Courtney Ryan’s videos, you’ve got a toolbox to spark meaningful, natural chats. From finding out what matters to them to sharing a laugh over a quirky question, these prompts help you see if there’s a connection worth chasing. Pick a few, stay yourself, and let the conversation roll. Let me know in the comments what questions you love for first dates or if you’ve tried any of these!

FAQs About First-Date Conversation Starters

Q: How many questions should I ask on a first date?
A: Don’t rapid-fire a bunch of questions. Courtney says to pick a few good ones—maybe three to five—and let them flow naturally so it doesn’t feel like an interrogation.

Q: What if they give short answers?
A: Try a follow-up like “What made you want to do that?” Courtney says if they’re still not engaging, it might mean you’re not clicking or they’re not into the conversation.

Q: Should I steer clear of politics or past relationships?
A: Courtney says a question about a recent event can show their values without getting too heavy, but save past relationship talk for a second or third date to keep the focus on you two.

Q: How do I keep it from feeling like a job interview?
A: Share your own stories and build on their answers. Courtney says finding their golden nugget—the thing they love talking about—makes it feel more like a real conversation.

Q: What if we run out of things to say?
A: Have a couple backup questions ready, and don’t sweat small silences. Courtney says pauses are normal and can actually make things feel more comfortable.

Q: Can I use these questions when texting?
A: Totally. Courtney says these tips work for texting too. Ask open-ended questions like “What are you passionate about right now?” to keep things interesting online.