15 Best Questions To Ask On A First Date 

‘Any history of Nazism in the family?’ ‘Who’s your favourite serial killer?’ ‘Do you know much about knives?’

The best way to get to know someone is not asking questions. But seeing how they react to things. Activity dates tells you a lot more.

Holy cow. I didn't realize how unready for a relationship I am until I thought about having to answer these questions.

The problem I have with some of this is the questions are being formulated by experts, who haven't been on a first date in probably 20 years.

I think the first date should be fun...no pressure, just have a good time. There were a couple of fun questions on this list, and those are the only ones I would ask. Save the judgy questions for the second date. It's important to show them that a good and fun time is a possibility with you.

I went on a date with a girl a few days ago and I had no idea what to ask her, for whatever reason could not get into the flow of the conversation and we ended up talking about menial things like school and rent. Safe to say, I completely blew it and she ended up leaving mid-convo to "get back home". Honestly, my ego took a pretty big hit 🥲 This video is a good jumping-off point I think, and hopefully I'll run into less blockage during future date conversations 😅

Totally agree on the conflict question. Asking someone "How do you handle conflict?" most times they're going to give an inaccurate representation of what they actually do in conflict.

The best gift question is an easy one for me. When I was a senior in highschool I dated this girl for a brief period, about 4 months. On Valentines day I took her to dinner & she ended up giving me a great gift. It was a blanket that she knitted specifically for me. I'm 6'3 so she knitted it for a tall skinny guy. She even knitted in a "made with love" badge onto it. I loved it & I think she really liked the fact that I liked it so much myself. I still have it, it's one of my most valuable possesions. I personally struggle with low emotional intelligence & social anxiety and some antisocial behavior tendecies, but that blanket that my highschool girlfriend made for me acts as a reminder of how good I can really make someone feel despite all of my shortcomings. It motivates me to fix my problems & become a better person so that I can one day have something like that again & make someone feel that good again.

those questions just make me feel like I am having an interview.

I used to ask the "What are you looking for?" question but it backfired a few times, made the girl think I was too intense on a first date. Men are very direct and think questions like this are fine, but a lot of women are not wired that way.

I really haven't been on to dates, but when the date is going well one of my favorite questions is "what is your most embarrassing moment." It typically ends with everyone laughing, and you can learn so much about a person based on how they answer it. How they deal with conflict, abit about there past, alot of times it can even lead to the things that they are very interested in.

1) 3:19 What made you interested in going out with me? 2) 4:27 What are you looking for? 3) 6:32 What matters to you? 4) 8:31 When you think of current political events, is there something that stands out to you? 5) 10:22 What does your work-life balance look like? 6) 13:51 What would you do if you had a week off? 7) 14:54 When you spend time with people, how often are you the one making the plans? 8) 16:46 How well do you feel like you compromise with others? 9) 18:35 What do you think is important for a healthy relationship? 11) 22:50 What is something in past relationships you needed to work on? 12) 24:29 Who is the person you talk to the most? 13) 25:26 What is the best gift you've ever received? 14) 26:58 What was your first impression of me? 15) 28:03 What made you most excited about going on a date with me?

I know first dates are basically job interviews but you don't want to make it feel that way. Be careful what questions you ask, how you ask them, and how many. I'd pick 4 or 5 that are most important and work them into the conversation organically so it doesn't feel like an interrogation.

#2 is a question that really isn't that effective because people aren't always 100% sure or honest about what they're looking for when dating. They'll say they're only looking for something short-term or casual, but in reality they actually want a long-term relationship and end up hurting themselves for not being truthful.

Hi Courtney, A lot of the healthiest relationships among my friends are from people that knew each other for months or years before starting to date. So for me, a big problem with online dating is that I feel that girls are looking for a really fast fusional connection that is really hard to get from 3-4 dates and if you don’t, it’s friendzone. I know that you already did, but would like to see videos on how to create really flirting dates to create that quick spark to not be friendzoned. You videos helped me a lot in the last 2 years, ty!!!

I think keeping it pretty casual on the first date is best, no need to dig into personal topics if you don’t even get a good vibe being in the same room as them for an hour 😂

Doing things alone! After a major relationship ended years ago, I decided to learn how to be happy on my own before any serious dating. Knowing I’d be happy in any case was a totally different mindset. The confidence that came from this was LIFE CHANGING. Thanks again Courtney!

I think, that the the first thing you need to do is to guide the conversation into the direction of the question you want to ask, so it feels natural asking that question. I often start with I like to do X in my time or If i want to relax I do Y, then ask "How about you?". In this way you reveal part of you and the person who you are talking to will be more inclined to answer this question knowing that you've already answered the same question a second ago. Equally important is to not over do it. If you ask all the questions in this way, on the second or third question your date will see the pattern and this will surely annoy him/her. Ask a question, try to keep the conversation on this topic for a few minutes, then jump to the next topic/question. There's an app called Big Talk, which has a million open ended questions which are great conversation starters and the greatest part is that those questions are divided by categories. Keep in mind that the most important thing is to have fun with your date, because if you both have fun, there's a great chance that there will be a next date. I would be happy if this helps someone. Happy hunting ;)

I'd also add in asking them if they have a boyfriend. I went on a date with a girl and if i hadn't asked, she would have never told me that she has a boyfriend. We're sitting down eating dinner and i find out she has a boyfriend.

Excellent video as always Courtney! On another note, I would avoid overusing the verb "to like" with attraction and dating. Rather than saying "Do you like this person?" or "Does this person like you?," I would personally be more clear with expressions like "I am interested in this person" or "I find this person attractive." I "like" a lot of women in my life but there are only a few that I am interested in dating.

"How do you handle conflict?" My answer is, "Well we'll talk about it to find solutions to what cause this situation and find compromise that both of us will be happy with." Still I'm looking forward to Courtney's take on this question. Now, these questions were interesting, but some were kind of repeating themselves a bit. Well the questions I will ask will be more fun and not you're in a interrogation room.

These videos about "best questions" have given me clarity on myself. I feel like a lot of people are looking for a "spark" on a first date and they want the date to ignite some kind of passionate chemistry and that's just...not. what I'm looking for. And it's not what I feel like I bring to the table either. I think that what I'm looking for in someone else, and also what I bring to the table best, is a sense of calm, comfort, warmth, safety - what other people seem to think is boring seems to be right up my alley. I'd rather go in that direction and lead with my best foot forward than try to play a character that I'm not. I think that's why all of these questions seem appealing to me, even the more interview-ish ones or the more farfetched. Something that helps get right into opening up is something that I'm going to value. Every question that makes me go "ooh I love that" is a question that makes Courtney's eyes bug out of her head. And that's okay :)

As "best gift"... the first and likely the only that came to mind is "my whole education" ... from my parents. They paid for the best school and college they could afford , and supported me through my whole career (doctor in medicine). Hard to beat that.

I agree with you on so many of these questions--it feels VERY much like a job interview. All my best first dates were just FUN! Just be curious about the other person. Don't be so heavy.

The quality of your consulting in your videos is beyond my expectations 🎉 bravo Courtney

Watching Courtney’s initial reaction to these questions was a great barometer to see how women are going to react to these. Thanks Courtney!

I think some of these questions are worth asking. And, some of these questions are worth waiting until later to ask or not ask at all. I would avoid politics on a first date. Now, asking them what they would do if they had a week off would be a fun question to ask.

My question would be "How big of a role does social media play in your life".

The way you dress matters. I went with the Ronald McDonald look once, her grandma magically got into a skydiving accident with a horse and she had to cut the date short. Still waiting on her to call back though. Don't know how the horse is doing.

Best gift is easy for me. My deep and abiding friendship with my best friend from college. He was always there for me no matter what the situation. He loved me for who I was as a person and the feeling was mutual. Unfortunately he passed away from liver cancer in 1995 and it was a great loss for the world since he was such an outgoing and loving individual who everyone saw as an asset to society. We met the first day of college in 1972 when we were people watching together sitting on a wall at the student union building. It was a blessing that was meant to be. His love and friendship for the next 23 years transformed my life and it was a tragic loss for me personally as well as for the world at large. It was a once in a lifetime gift that I reflect on regularly knowing what a true friendship looks like.

These are mostly job interview questions and rather intense for a first date. Might be good for finding a "match" but not necessarily for getting a second date, which is the real struggle for guys. I would scatter these type of questions across several dates if anything, and just focus on fun questions for the first date or two integrated into

One of my favorite questions to ask my dates (although usually for 2nd or 3rd dates) is along the lines of: "what is your unrealistic dream?" In a playful manner, and usually giving examples of stuff such as going to space, or meeting dead celebrities or historical figures. It usually gets a nice conversation rolling by sparking an interest in something that person deeply likes.

Skip the standard questions/answers game. This list is as good as any but not really avoiding the interview. You want the 1st date to be FUN!, not a survey. Not a mundane psychological exercise. First dates purpose is to create an idea in her head that you are fun to be with. You must produce 'energy'. Humor is good, but excitement is even better. The first thing I want to know is if she's 'merry go round' or 'extreme roller coaster'. You want to know what sort of fire resides inside her, not how many brothers and sisters she has and how old (it's not harmful, but not now). The best question ever, to produce an energetic discussion, create automatic back and forth, make laughter and adrenaline is: "Tell me of a super scary, weird, funny, uber extraordinary thing that you've seen or where part of." Have a few of your own ready. Tell her you'll go first if she's hesitant. Then in an animated way, tell your weird, funny or scary story. Car wreak, seen a UFO (I have), other supernatural phenomena, was in a tornado, almost drown. Any story that is scary, weird, funny or exciting. Everyone has had WTF moments. When you first meet you concentrate on FUN, not mundane. Plenty of time to share metrics, they have almost no importance at all on the first date, but that's where people go...yawn. " I", would NEVER ask the question "what made you want to go out with me?". What if I don't like the answer to a question I don't really care about? Your purpose is NOT to put your date on the spot. It isn't an inquisition and that's not fun.

You could always start by telling a story. I know we all have a story about buying something and either being excited to read the instructions on how to assemble it or just start by not reading and trying to assemble. Then you could ask are you somebody that reads instructions on things or just start trying to figure it out. And you can sure proceed with asking her to share an experience she can remember 😉.

I'm glad I'm not the only one who found some of these questions odd Thank you for expanding on them and reframing them to sound more natural

One question I've thought of that can gauge someone's interests/desires: "If you could eat dinner with any three famous people, living or dead, who would they be and why?"

"Do you like me?" is a socially heedless question for a myriad of obvious reasons. If a girl is going out with you, she probably does have at least a surface-level interest since she decided to spend time with you unless it was a blind date. And the whole purpose of a first date is to get to know the other person, so the answer might not be clear until the end of the date. I can understand why you would want to gauge a potential partner's political/religious views on a first date to determine if you share similar values, but I feel like this can cause a lot of unnecessary tension and ruin the vibe because discussing contentious topics can rapidly escalate and cause the dynamic to become incredibly awkward.

When you meet somebody for the first time, you're not meeting them, you're meeting their representative. Chris Rock

A lot of these questions really reinforce that experience is where you find wisdom and not a PhD. Your insight, as always, is greatly valued, Courtney! Thank you.

There are different ways to handle conflict and one way I know is this tell them this mantra. " I'm sorry I have cause you pain, which made me suffer but I am here for you."

Love your content. I've been recommending you to friends because you're videos are just full gems for dating etc. thanks.

I like the "what are you looking for?" question, but that's about it. I mean I can completely understand trying to learn more about your date, but you need to be mindful of how you come across too, and it's definitely not like a fun person to be around if you ask all these questions. Plus with a lot of these it feels like you're almost trying to look for what could go wrong instead of focussing on what's right or unique about the person you're with.

I think the best questions are ones with verifiable answers. Most of these questions you can't tell if they are being honest or not, and they may not know the answers themselves. If you ask what book has had the biggest impact on them, you can read the book in a few days and discuss it with them. If they have a good grasp of the themes of the book then you know they really read it and you learn a lot about them by the types of books they like. Hypotheticals like "what would you do with a week off" don't seem useful unless they have a week off coming up. 1. they can lie and you wouldn't know 2. they may not know They really can't think about that question very long on the date or the pause would be awkward. And if they don't have a week off in the near future, they may not have spent much time planning it. So their 30 second off the cuff answer probably doesn't isn't what they would really do when they take time to plan a real week off.

These are never questions I would have imagined asking on a first date. Or honestly questions I will want asked. To me they all sound like job interview questions.

I cherish my education as the most valuable gift I have ever received. It provided me with the freedom to explore my interests, entertain my talents and define my ambitions through nine years of college, Biology/Economics B.A. Econ. and Pharm.D. in Clinical Pharmacy, without a financial burden.

My grandfather once told me that first dates are a "tiptoe through the tulips", a military euphemism for walking through a minefield; one wrong step, and there will be consequences. 😅

the best gift I've ever gotten was a book: these people knew me so well they sent me home after a dinner party with an incredible book--absolute gems these folks. The only gifts I received from girlfriends were clothes that made me look more presentable, for HER to stand next to...really had nothing to do with me per se

If I go on a first date with somebody I won't bring up any questions to make her feel uncomfortable like it's an interview I don't want her to feel like I'm being judging her. Just wanted to have a good time with her enjoying the scenery having great conversations about anything but not making her questioning herself in any form of ways. 2nd date same thing ain't bring up any questions like I'm doing an investigation. On the 3rd date. That tells me she's still interested that's were I'm asking my favorite question of all time. What are you seeking for in a relationship and what are your plans, goals for the future? So by that time she's already felt comfortable with me answering those questions truthfully. Reveal there true self// What is my favorite gift someone gave me? My answer to that comes from my heart, is being there with me in good time and bad. That's all it matters to me, sharing those magical moments that I call it real friendship real love.Those memories I will never forget till I die. Yes that's my answer to that question ( real friendship) Off course no one is perfect but we 10:57 need to keep those memories alive. Those moments are special.

The best gift I have received was an institution size can of pork and beans. This was from my college roommate'sfiancé who also gave me the second and third best gifts -- embroidery scissors for fine trimming of my beard and an antique Burgie Man bottle opener. After 40 years, I still have the 2nd and 3rd. She lost her marriage after 23 years.

Courtney, you hit the nail on the head, regarding success and workload. My better half is fine with my workload, but she's also a workaholic. I've dated women who liked what I made, but hated my lack of free time. There is an opportunity cost to everything.

One I like to ask: If you didn’t have to work for a living… what would you do with your time?

I'm not sure... to me many of these questions are quite heavy for the first date. Or they still feel like a job interview. There are some good ones (e.g. if you had a week off - how would you spend it etc.) but on the whole.... I would spread these questions across 2-3 dates + added a few more light-hearted ones.

much more important than what you ask is "how" you ask things. imo. my goal is not to collect massive amount of data, it is to create connection. so keep it playful and friendly.

5 of my go to questions on a hypothetical date: 1- What was your favorite class in school? This can be a really good jumping off point (do you still like it now, what did you like about it, etc.) but also in itself say quite a bit about them too. If they say Gym class, they’re probably into physical activity and/or fitness, if they say Drama class they’re probably really into Theater, etc. 2- Where is one place you would most like to visit in your lifetime? Firstly this can be a great question for a long term relationship and if your memory is great it can give you an early idea for a honeymoon or holiday vacation trip, etc., but also it could say a lot about the things they value too. If they say New York City maybe they value Theater and Broadway, or if they say Florida maybe they care about warm weather and enjoy the summer time, or if they say Paris or Rome they may value Culture and Cuisine/Food, if they say something like Russia I might get a little bit concerned since despite my love of learning and being inquisitive (sometimes to a fault) I’m not overly into the whole daring and mysterious vibe. I like adventurous, but there’s a little bit of a line for me. 3- What is one thing that you love about yourself? I feel like for me, this is a great question to help them feel a bit more confident and secure if they’re feeling nervous, gives them the chance to talk themselves up, but also may show what they might be looking for in me as a partner. If they say my favorite thing about myself is my Intelligence, then that may signal they’re looking to see if I’m intelligent enough for them. It also gives you an insight into what they may like to be complimented on. If they say their favorite thing about themselves is that they’re a hard worker, it’s more meaningful to compliment them on how well they performed at work, for example. And MOST importantly, it’s also a little bit of an ego and vibe check. If they say their favorite thing about themselves is that they’re sneaky or mischievous or something like that- probably not a fit for me. Or if they’re like Oh my god I love how humble I am and how I’m never egotistical and self centered and I never act like I’m the best and I hate talking about myself and I just hate people who are egocentric and everything because I’m totally not like that, etc. you can get a feeling for how they actually are too. 4- What is one thing you learned this week? One thing that personally matters to me in my life a LOT is a love and hunger for learning and personal growth. I always strive to be trying to learn something new, even if it’s a minute, minuscule, small detail. It can really say a lot about our personal fit together for me personally how much she shares that passion, but also could be a sign of intelligence more generally. Most importantly though, I think it’s a sign of humility. One of my life mottos is that it’s really important to know how much you don’t know. So if she comes out with an answer like Nothing (for either reason either because she did literally nothing to learn anything all week or she’s a know it all) it’s not gonna work. Or if she says 5 billion things, then that’s probably a sign that MIGHT point towards lacking that intelligence previously on the worst side of things or on the better side of things is she may be just trying to impress me and just feels like she needs to do that which may indicate a level of insecurity there. 5- What is an animal that you see part of yourself in? For one, this can be a great way to judge what someone thinks of their personality in a more indirect way than Question 3 in the sense that this leaves things a bit more broad and you’re not pigeon-holing them into talking about their one favorite thing they like the most and forcing that decision making process to click. It’s also a little bit more light hearted and allows for a more fun conversation topic, but a negative answer could also be telling. For example, if someone says they think they’re like a jungle cat (like a Tiger or something) that can be a bit intimidating and daunting in some ways depending on how they explain the answer, while if someone says a Dove or Swan, that could be almost the opposite and be like the first thing you think of yourself being is peaceful? That seems a bit of an oversell at best and at worst is a downright lie.

Given me a lot of background knowledge. Many thanks.

Argggh! These questions are so transactional in nature they'll just drain all the fun out of a date! How about this approach: "Hi, very nice to meet you. More than anything else I just wanted to come out tonight and have a really good time and for YOU to have a really good time too. So, for the first couple of hours, why don't we try to have a nice meal, in good company, with fun conversation. So, if you'd like to talk about hobbies, travel excursions, amusing stories about family and friends, I'd really love to hear about all that! There'll be plenty of time for more serious questions later, but for the first two hours why don't we see if we can both just relax and have some fun?"

These questions were very helpful and opened up ideas for my own questions. Thank you.🌺

These are all good and reasonable questions, but they should definitely be spread over several dates. I think the purpose of the first date is to understand whether you would like to go on a second date, and a good question to ask yourself would be "how much information from this person can I handle, supposed we might never see each other again?" I think the conversation on the first date should really revolve just around the person in front of you, what they are doing at the moment, what are their hobbies, what is their education. Questions about family and their relationships with other could really be saved for later dates

About question 7. I guess that is one of my red flags because I don't plan things with others. But, in my defense, I don't expect others to plan things for me either. I do have friends and we do get together frequently (we are all active in our church so we see each other often) amd I am pretty preoccupied with working on my future goals whenever I am free. I am introvert at heart so I am very fine being by myself and not planning random get togethers, but if I were in a relationship I would totally plan stuff since I am a dude and I want to lead my future partner. Maybe I'm wrong 🤷

I think instead of asking if they can compromise a better question would be to ask if they have siblings and see how they react if they do. How well someone gets along with their siblings can tell you everything you need to know about how well they compromise

Doesn’t matter if you get ghosted after the second date.

Best present: bristolboard presentation of our dates over the last year and all the things my partner appreciates about me.

Not much dating experience but I would think on a first date let the conversation go where it goes.

You are very kind Courtney, thanks for your thoughts--they are helpful to this poor bastard of a man who needs such advice

well it wasnt so much of a gift as me taking it in the beginning. it was this little red panda stuffed animal that belonged to one of my brothers. i dont know why i grew so attached to it but eventually my brother gave in and stopped trying to get it back. that little guy has seen me through some of the toughest times in my life and i still have him around today.

I asked all of them throughout a date or over multiple dates. The questions should reflect what you are looking for in someone. As for changing them don't try, no matter how long in a relationship if she originally said she doesn't want a relationship and you do walk away.

These questions will get you ghosted and you will never get a second date. Don’t ever ask about politics or about another relationship you had. If the girl is talking about her ex a lot just move on she’s still in love with him.

For 2, men looking for something casual will wait on the woman to answer first and adjust their answer accordingly i.e. if a woman wants a relationship the man will reply with the same even though he's looking for sex, one for women to be wary of

Thanks, Courtney. I went on a first date today. It was better than I thought. I'm a skydiving instructor, so I took her on a skydive.

Ask about what fun activities they do when with friends or family, or questions like this, keep it light-hearted. Generally questions like this, has given me the red flag moments without directly asking some of the questions listed above in video. Some of these questions are too formal and may turn off a potential great partner who just wants a relaxing conversation.

Maybe a better way to go about asking 'How do you handle conflict?' - and most of the 'formal' questions on this list - is to simply give your own perspective first and then bounce the ball back to them. Like, "I'm the type of guy who would throw a tantrum over you even suggesting something that I absolutely don't like., like what ice cream I should try, for example." "If you were to suggest a certain flavour and I DON'T like it, I would totally lose it." Then say, "Just kidding". And then continue by saying, "but seriously though, have you ever experienced a man behave like this?" "And how would you react if I were to really do this?" This a way more casual and fun way of 'adressing' the same topic. Cheers!✌

I love the 5 years question as a goal oriented person. Also the week off question as I get 9 weeks off a year as well as lots of vacation due to being a shift worker

Yeah, a lot of these questions are too job-interview-like. My best question to ask is about their travels. Where they've been, the farthest they've been to, their last destination, their favorite places, etc. There's always stories behind people's travels and sweet spot moments to share.

Hi, Courtney! Andrew Keener here. The best gift I ever got ... likely when my brother (only sibling), sister-in-law (in-law for documentation only), niece, and nephew came to visit me the day before Father's Day (in the United States) 2021. My sister-in-law, niece, and nephew brought chalk (there's a chalkboard placard outside each apartment in the building where I live. They drew on it. I still have that artwork up. Not really a gift, but. I also probably call my Momma and Dad a lot. So, likely talk to them for sure. I also have a Filipina aunt (widow of one of my Momma's brothers) in Indiana. She and I text and talk sometimes. My Momma's remaining brother (retired California Highway Patrol) and I text and talk sometimes too. I also text my brother and sister-in-law too. But definitely my parents. My brother and I share the same parents. Momma and Dad are still married to each other. Since May of 1980. If that makes me a momma's boy ... I'm cool with it. When was on dating apps ... sometimes I would ask tell me something about you that I wouldn't be able to find out by looking at your profile.

I am going to have all these questions on index cards and ask in rapid fire succession within a five minute speed dating period. Whomever can answer the most questions "correctly" wins.

1st date have zero expectations and you can’t be disappointed

I feel personally asking 2 or 3 of these questions before even dates will save a lot of wasted time. Engadge with the person your interested in. Everyone is either looking for a long term relationship or just fun.i have interest in a woman and not going to ask her out yet until I see if something long term can come of this. So far so good soon I'll give this a go. I want to make sure I don't jump the gun so I'm not wasting time. I see she's interested I'm just making sure if pursuing her is worth it. So far it seems so but as stated I'm making sure. I'm getting to old wasting my time.

The question: how do you handle conflict?--- is an important one; but more important is that "I don't know" does not always lead us to think that they cant handle it-- just that they may recognise that not every conflict demand a particular response. in other words, not every conflict require the same measured response.

It depends on where you live: in NYC it is natural to work weekends, in LA it is not. Maybe you should select city before starting to date?

"How do you handle conflict?" and eluding to political interests are probably the single best predictors of relationship satisfaction.

I really appreciate you, Courtney, thank you.

Today's first dates are like an interrogation at the police station... A woman will get more information from you than a police officer😂

I cannot see a woman responding positively to questions about compromise and conflict resolution on a first date. This whole list seems geared for women to ask men these questions.

Ehh, many of these deal-breaker type questions are things you should learn about a person before even going on a date with them. Weeding out the most incompatible people is what dating apps SHOULD help with, but often don't unless you pay for them. Honestly, I think it's fine if very early interactions with someone feel like a job interview, that's basically what it is. Maybe I'm insane, but I'd love a dating site that looked like a job site, where each profile had a long list of criteria you had to meet, and you had to "apply" to go on a date with people. The prospective "employer" would look through "resumes" with no photos to start off with (to avoid simply dating the hottest people who aren't compatible). Then after wittling it down to only the candidates who best fit their criteria on paper, you might have the option of seeing their photos. It would save so much time and frustration from the get go.

In my love languages I like to give gifts. However, I fo not know what receiving gifts does not f do obit for me. Although over time I get up appreciate some gifts. Meanwhile, the best gifts that touch me is the care, attention, love, thoughtfulness that somebody expresses to mdd we through their gift. I am not including such drawing or ‘l love you dad’ written by my kids when they were little. These papers and drawings are more precious to me than jerkers or other gifts I received.

My buddy owned a very established and very profitable pizza shop. He got married, had kids and she loved the money but then a few years later started complaining he was always working. He said i will sell the shop and get a regular job. He did and she now didnt have the same income and divorced him anyway.

Real love is my best gift I'd want to know if the person is open minded (I tend to be quite imaginative and want to see if they would jive with me: so to speak) While I can value down to Earth thinking for practical reasons, I value openness to possibilities even more (like outside the box thinking) because I like creative energy and innovation

planning.... i think that depends on the type of work they do. I've had a lifetime of military so constant long hours at work, suddenly working weekends or shift changes, deployments, so over 30 years of plans not happening you learn to do things on a whim, travel, go to the beach, find a place for dinner, grab drinks with friends.....also why there is such a high divorce rate in the military. After retirement though, at least when not working i'll have months at a time off to do anything and no one to do it with.

One of my go to first questions, is if the person likes drinking water.

This gives me more the vibes of a job interview. When on a date just talk about random/fun stuff and be intuitive with your questions during these subjects, showing interest in her. Why prepare a whole list, it makes it very unnatural. Listen well, go with the flow and trust yourself

The every best job interview I had was being asked to tell my life story from birth. Every detail. Its impossible to make up or fake your life story. It so easy to do and it prompts easy natural questions on the way. I got the job. I am 40 years beyond dating but I got to know my wife and she got to know me in that level of detail before we even went on a date.

A girl on the second date, when I invited her to my place, asked me, "Do you love me?" 😅 I said yes and still did not work.😂

Honestly, IMO, there are NO good questions for a first date. Or rather, there are no specific questions you should be looking to ask. First date is simply to se if it's someone you can enjoy spending time with, without necessarily having an "end goal." Because, ideally, that's what makes up the majority of any long-term relationship, if you can't do that, there's literally no point in asking any questions. It does not matter how well your morals, ideals or life goals align, if you can't enjoy just spending time with that person.

The best way to get to know what a person is about is not what they say about themselves but more so what they say about others! I just broke up with a girl I was seeing for a short period of time she was a covert narcissist and would've skated through most of these questions with flying colors!😅

Absolutely avoid an interrogation if you want any spark. I had a video call with a woman Friday night, 45 minute interrogation really turned me off.

I would easily go on a thousand dates, answer these questions and NEVER get a second date. But... that's mostly because I'm old, ugly, only 5'10", and not rich. However, I love your stuff Courtney.

I totally like the word “ in tune what’s going on in the world”. The thing is politics and religion are very sensitive subjects. However; been in disagreement means the other person is a bad one ? We can disagree but respect each other. I guess all depend of the person how much both subject truly matter but also could be missing out there.

Can you make a video about how to get the date in the first place? Like how to approach, what things to talk about

Courtney, as always appreciate your content, but some of these ?s are awkward & come off as needy imo. Agreed with your comment on the gift from her ex, lol. I think it's best to stick to simple things like someone's passions, goals, dreams, fears, insecurities, then try to emotionally bond from there. Celebrity crush, binging on Netflix, things like that can really add some laughter & light heartedness too.

I agree completely... BELIEVE someone when they state what they are looking for!