199 Questions to Ask a Guy (Dirty, Personal, Funny, Awkward)

You’ve probably been a skilled talker your entire life! Whether it be school debates, negotiating a longer night out with your mom and whatever else. If you thought you weren’t, believe us, you were. You had it within you all along, you just didn’t know how to harness that power. You may be a master of the art of chatting or not, but only one thing’s for sure. Talking to your dream guy can be a thing of dreams and a nightmare at the same time. How is that possible?

Well, that ideal first date, or whichever ordinal number is it, is a challenge. You are faced with the man you’ve always dreamed of. At the same time, you know that there is a high chance that something will go wrong. We’d like to start this advisory piece with one thing – things never go as planned. The first step to every conquest in life is relaxation. You are where you want and your goal is to be you. It’s a natural phenomenon.

The key to every good conversation is just to keep it going! At times, especially, in the beginning, it’s good to have a plan. Knowing what questions to ask is a useful tool to make things right. Knowing which questions to avoid is important, too.

Sharing is more important than you thought

You may hate her taste in movies, but she might love your taste in interior design. By sharing experiences, facts, and secrets, you will both be richer people. The whole point of a good relationship is making your man a richer person spiritually, and vice-versa. No matter how much you differ, it’s easy to have date number two in the bag. Making a good impression is essential.

Of course, we will cover a wide range of areas. That’s all to make you the best woman you can be. You have it within you, girl. It’s your turn to shine, but there are some golden rules when conversing with your man.

Never interrogate him

The whole point of a conversation is for both of you to feel equal. He will love it and appreciate if you let him do the talking, too.

Have an arsenal of tricky and baffling questions!

They can open a Pandora’s Box and be a gateway to some more interesting topics. You might even forget which question did you start with. It’s all about establishing a comfortable atmosphere.

Be ready that a question might backfire

Not everything will go according to plan. Not everything will be planned. The beauty of his mind and your mind will be evident in those awkward situations. Relax, he’ll see the real you through such spontaneous banter.

Guys, generally, have a hard time opening up so quickly. That’s perfectly fine and you should respect his space. It may take a few questions to spice up and open up the conversation. When he sees that you see him as an ordinary person, he will feel less pressure.

And there you have it. Who knows where that sort of banter might end up? The next date? Your place? His place? A house with two kids and a big dog? Who knows! Differences make it fun!

Good Questions To Ask a Guy

Every good conversation is due for a good foundation. Guys may be hesitant at first, but they too love to tell stories. It’s long been a misconception that only us gals like to tell tales. Telling something in the form of a story is a good form of self-expression. Men are no different. They just take a little bit more time, that’s all. The key to asking these “foundational” questions is just to be patient and warm towards your guy.

Like anyone, guys share their true opinions once they trust the person. Even though they might not do so right away, it can come gradually. As they tell their tale, they will free up once they see how carefully you’re listening to them. That’s the only way to reassure your date. Through patience, time and a calming atmosphere, everything is possible! These questions are specific but open-ended. You can modify them, or ask additional ones. By date two, he will be sharing his fantasies with you!

• I would like to hear about your hometown…
• What’s your family like?
• Do you have a nickname? If you do, how did you get it? Do you like it?
• How would you compare your current town and your hometown? Which one do you like? (If he still lives in his hometown) How did the town change over time?
• Are you happy with your job? What is your dream job? If you work you dream job, what would you change?
• Tell me about your friends? What do you value the most in a friendship?
• What do you value in a movie?
• What’s your favorite way of traveling a foreign country? Camping? Expensive hotels?
• If your life was a movie, who would have the lead role and why?
• What kind of an experience do you have with pets?
• Do you have an older brother or sister?
• What was your first drunken experience?
• What was your first trip abroad? Did you like it?
• Did you take up any sport when you were a kid?
• What skill would you say is your best trait?
• What thing about your childhood do you miss the most?
• What were you afraid of as a child?
• What’s your favorite flag and why?
• What’s your ideal name for a child? What’s your least favorite?
• Can you juggle?

These questions right here are excellent conversation starters. They can also be asked out of the blue, in order to break the silence. Your man will like that you’ve taken an interest in such topics. His tongue will unravel and you will get to know him a lot better.

Not only are these questions safe, but they also open the door for the next set of questions. By knowing his upbringing and other details, you will know in which way the conversation will go.

Interesting Questions To Ask A Guy

Now that you’ve laid the foundation, it’s time for fun. You know about many aspects of his life and you can see what kind of a person he is. This is valuable material and you can mostly relax now. The first set of questions is always the toughest because you’re treading in unknown territory. Thus, you can rest easy once you’ve passed that part.

Everyone likes challenging questions, men especially. Their whole being is wired to accept challenges and adore them. These interesting questions to ask a guy should be both playful and intellectual. Guys like to show what they’re made of. Imaginative scenarios and opinions should be the motive of this part of your journey.

It’s best to test the water, and still come off as a confident gal. As the conversation topic get more interesting, he and you will become closer. Politics, religion, and money are big no-nos! Unless you approach religion accidentally, don’t venture there. If you do, be respectful and aim for spiritual knowledge.

• What would you bring to a desert island, if you could only bring three things?
• What is your stance on social media? How long could you live without it?
• What are your main criteria when picking a phone? Brand, specs, looks, recommendations from friends?
• Did you ever have a paranormal encounter? Are you sure about whether they’re real or not?
• What celebrity would you like to meet and why? Do they deserve admiration?
• Do you think that people that star in a reality show have self-respect?
• How would you describe karma?
• Without concrete evidence, how can you dispute the existence of a higher force?
• Okay, this question will make or break this – cats or dogs?
• How do you think the world will look in 30 years?
• Will there ever be a WWIII?
• How do you feel about police brutality?
• If there is one meal you could eat for the rest of your life, what would it be?
• What meal wouldn’t you eat even for a million dollars?
• If you won $10 million on the lottery, what would you do with it?
• If you could live in one period of history, which period would it be?
• What world leader would you sit down and have tea with?
• Which ghost would be the funniest to hang out with?
• Coke or Pepsi and why?
• Burgers or tacos?

If the first set of questions is for foundation setting, this one is a gateway to other topics. Are we alone? Is there a higher force? The key component about answering these questions is the use of ARGUMENTS. Men love to reinforce their opinion. A person is at their best when elaborating what they believe in.

Even if he doesn’t state his religious affiliation, you can talk about spirituality. An important thing to note – if he says something you disagree with, move on. Asking why, because you’re irked, will show him that you’re invasive. That’s a big no-no. Respect is the way to go!

Beware, interesting questions carry interesting answers. You will dig right into the core of his being. You might like or not what he says. Act boldly, but with warmth. You will sweep him off his feet.

Flirty Questions to Ask A Guy

Opening up the conversation and challenging someone are the first phases of every chat. We like to call them the test drive. If you like what you hear, you can move onto more delicate subjects and try to reel him in. Flirting is the key. It’s all about being fun, but with a seductive note. Using the right tone and making him second guess your question is what you’re looking for.

Feel free to loosen up and relax. Harness who you really are because that’s all you need! Whispering in his ear with just a touch of breathing will make his heart go into full throttle. Have manners, as they are the separation factor between a good time and disrespect.

Just be yourself and relax. Respect should be the basis and everything should just flow from there.

• I’m a born sinner, do you wish to risk the fiery depths of hell with me by ordering that chocolate cake?
• Care to sink your teeth into my meal a bit?
• In love and war, is all fair? Why not? What’s the difference?
• Shall thee be tempted to lay your teeth into my… dessert?
• Care to share an Italian kiss or more than a few? (It’s the name of a known chocolate ice-cream, but the name is a boom in one’s imagination)
• Can I trust you with a dirty little secret? (Guys love intrigue and mystery. He will feel entitled and honored to hear what you have to say. You can share something significant or dirty. But, an anti-climax is also a good tool to use. Say something medial and laugh about it as a joke. It’s a good way to check his sense of humor, too)
• Care to go with me on an adventure? Let’s say rock-climbing, sailing. How does that sound?
• Which part of your body would say is your favorite?
• When it comes to the female body, which kind of look do you appreciate?
• I’m sorry for looking at you hard, it’s not that you’re gorgeous or anything. Can you forgive me?
• Do you think you can maintain eye contact longer than me?
• Did you get your shirt custom-fitted or was it dumb luck that it looks so good on you?
• Do you think that this light does us justice?
• How would you feel if we moved our location to somewhere more intimate?
• In an ideal world, would you go for another drink?
• How much takes it to get you slightly tipsy?
• Would you see me home? Just in case…

This section is all about being suggestive. This includes sending him a message that you want to tell him your plans concerning him. This is a high stakes area of a conversation and you might seem things not go to plan. That’s perfectly fine! He won’t mind if he sees that you don’t mind. Backup questions are important, too:

• Did you try a cuisine from every continent?
• What’s the most insane thing you’ve ever done?
• How open to skinny dipping are you?

If flirting doesn’t go as planned, this is a side street! By asking him adventurous and naughty things, he will get the message. The message is that you’ve thought about that too, right. It’s called planting seeds in someone’s head. Oh, and the best part? You will share funny stories, remarks and enjoy your collective sense of humor.

Dirty Questions To Ask A Guy

This territory is not for the faint-hearted. Especially because you’re a lady. When you’re a lady, you should do everything in a ladylike manner. This includes dirty talking, too. Be colorful and imaginative, but subtle. Make him understand exactly what you mean, but don’t use literal language. Now that he trusts you, you can move a little bit faster, but still with caution.

Being too open and literal leads to him misjudging you for a girl with questionable morale. Sexual desire is something natural, but only when connected to a genuine liking of a person. Contrary to popular belief, men are not animal. They are like us, but take a little bit more time to open up.

Note that dirty questions to ask a guy are a weapon for later dates! If you’re dating for some time now or when you’re close, only then. Earlier attempts lead to miscommunication and misunderstandings. Learn to “sniff out” the situation. If it’s casual, go for it!

• Whose place do you think has a better interior design? Wanna find out?
• How do you feel about a nutritious breakfast after a long night?
• This place is too public, wouldn’t you say?
• Tell me a fantasy that makes you tremble every time you think about it…
• Is it true that the lips of a stranger have the taste of excitement?
• Want to go on a cocktail binge and see where we end up?
• Let’s put those ears to work… Here’s a fantasy of mine…
• What’s the sexiest movie you’ve ever watched? Wanna watch it yet again?
• What’s the most sensitive place on your body?
• What place on my body do you think is the most sensitive?
• It’s high time you put those sexy forearms to use?
• Do you have a map? Because I think I got lost inside of your eyes.
• How do you feel about us ditching this dinner and heading somewhere else?
• Sorry, I get carried away by just looking at you.
• Is it legal to stare as much as I stare at you?
• What section of your body do you hate the most?
• I think you might wanna hear this fantasy…
• I like how you make everything else feel irrelevant…isn’t it?
• It’s never dull with you, isn’t it?
• You’re like a walking inspiration for dirty thoughts…

The social rule that girls should be passive is an awful and conservative one. You’re both the same and that notion will bring a smile to his pretty face. With you taking initiative, he might become more liberal himself. By pacing yourself, listening to the signs and choosing the moment, you can strike gold.

Intimacy and going to each other’s places are just about physical contact. You will both become more caring and free with each other. If it doesn’t turn out to be like you’ve dreamt, you gave it your all. And that’s important!

Sexual Questions To Ask A Guy

Sex is all about responsibility. Before we head down this road, it’s important to know what sexual questions are already for people who are established. These aren’t for first dates, nor second ones. First of all, you should share your attitudes about protection and STDs. Your safety is of the utmost importance. Never forget that!

If your relationship is moving in a more physical direction, be gentle and sense the moment. Scrap every playbook before you make a move. He may share details about his past lovers, experiences, mishaps, and everything. But that doesn’t mean you should force it. Relax and respect the boundaries of the situation.

• I know a good, sexy movie. Would you watch one with me?
• I’ve been researching striptease a bit… Want to see how proficient I am?
• Did you ever try bondage? To me, it sounds interesting/scary.
• Damn, who turned up the AC? It’s hot in here.
• What are your feelings about roleplay? What’s your biggest fantasy?
• Are you aware how beautiful you look in that hoodie/shirt/to me/always? (News flash! Men are people too and they also have their insecurities. Everyone appreciates compliments. By complimenting him, he will smile instantly. Men love when you take notice of their effort, it’s what keeps them going. Compliment his traits and capabilities too. Men that only care about physical compliments don’t exist, contrary to popular belief.)
• Want a massage?
• It’s cold, we could use a blanket….
• What is a sexual experience that you would like to forget?
• What is a sexual experience that you could never forget?
• How was your first time?
• What areas of making love do you think you can improve at?
• Did you ever burst out of laughter during sex?
• Casual or passionate?
• Rough or gentle?
• What is the craziest idea that ever got born inside of your mind?
• Are you more active or passive?
• I feel free next to you…
• It’s a sin that you’re not take, but I guess we have to stop it somehow…

Have you thought about working out? You’re excellently predisposed. (If he’s working out, his effort will go noticed. If he doesn’t, you will motivate him to go and give him a reason to do so.)

There is no strategy and no playbook when it comes to this part. It’s just feeling out the situation and letting your mind roam free. Don’t force it. If you don’t talk about such things, don’t worry. It will come on its own.

Deep Questions to Ask A Guy

Now we’ve reached the fuel of every relationship. The tacky, the tricky and the strange. The thought provoking, if you will. These questions and subjects make you take your man’s hand and tread into challenging territory. When you’ve realized that you have a lot in common, it’s time to embrace the differences.

This is all about debate, asking sub-questions and exploring your minds. He will love an insistent and curious woman such as yourself. It will open new gates, new options, and new conversation topics. Such conversations are also important life lessons. You learn to respect opposing views and learn about why other people hold such views. This is all about debate, opinions and differing views. Having fun and knowledge at the same time.

• Do you think there is life after death? What about life before life?
• What is your stance on capital punishment?
• Is global warming real? Storms have been going on for ages, is it possible that global warming is just a cycle of Mother Earth?
• Can money buy happiness? What about the fact that happiness while working can lead to more money?
• Are drugs necessarily bad or is it just the people who tend to use them?
• When do you think euthanasia will be legal? Are you for it or against it?
• What is your stance on abortion? Do men have an equal say when it comes to keeping the child or not?
• Is work a goal in itself or should it be just a means to achieve the ideal life?
• Should technology be considered good or bad for us?
• What’s your secret when it comes to coping with stress?
• How do you think the pyramids were built?
• Do you think communism will work?
• What is your opinion on the Vietnam war?
• If you had the option of dying for your country, would you do it?
• Would you sacrifice your life for a loved one?
• Do you think reincarnation is possible?
• Is what cases is crime ethical?
• Should drugs be legal? If yes, under what conditions? If no, why?
• Do animals deserve the same rights we have?
• How do you think the world will end?

These questions move to the most interesting and most mysterious territory of a conversation. You can find out a lot about his principles and the core of his being. Belief systems, social issues, and concepts are all in play here.

The key to this set of questions is to not include too many. Another important thing to consider is letting your man talk as much as you do. When he sees that you’re patient enough to let him speak, he will see that as a sign of respect. You should also be careful about asking too many questions!

Men hate it when they feel like they’re being lectured. It’s in their genes to try and prove that they are capable. They understand lecturing as an accusation that they aren’t capable. If you sense that he is reluctant to speak about a subject, share your own view to encourage him. If he says something you disagree with, don’t act disgusted and insult him. Say something like “Interesting point of view, but I don’t agree with you. Can you elaborate more so I can understand you better?”

Funny Questions To Ask A Guy

The questions are always needed. Whether it be the first date or the 23rd wedding anniversary, you can always use them. Men are shier to talk and are reluctant to be themselves when they don’t know you. By asking him such a funny question, he will know right away about your sense of humor and wit.

When he finds out about that, he won’t hesitate nor be afraid of a blunder or something else. The key is to establish trust. He will love you for that, we’re sure

• Did you know that in Africa, for every minute here, there passes 60 seconds?
• Can you impersonate a celebrity? What would they think if they heard you? Come on, don’t be shy!
• Did you know that Kiwi can mean three things? A bird, a fruit and a New Zealander!
• Would you join a reality show like Big Brother? Would you be serious to win or would you want to have fun?
• What was your worst embarrassment ever? How did you live it up?
• Have you ever eaten something disgusting, but only found out later about it?
• What was your funniest drunken adventure? How did you manage to return home?
• Did you know that Ancient Greek philosophers invented working out? How big of a biceps do you think Plato had?
• If you could throw up on one person, who would it be?
• What would you do if you caught a lion sleeping in your back seat?
• Do you think a bear can juggle?
• What was the funniest joke you’ve ever heard?
• Do you condone dad jokes?
• How far do you think black humor should go?
• The only way to resist you is through 3 restraining orders…
• Did you know that eating pizza every day is healthier than dying?
• What is the stupidest way to die?
• If you were born again as Hitler what would you do?
• Do you think cockroaches have souls?
• Wanna see how much alcohol it takes to die?

The questions are an ideal mix of appropriate comedy and some fun facts. Both aspects make you seem both knowledgeable and relaxed. If he knows about a certain fact that you’ve asked him, he can elaborate. That’s an excellent excuse to prolong a conversation and maybe take it somewhere else.

Random Questions to ask a Guy

One of the biggest reasons why men lose interested in a conversation is that they sense it’s all planned. You can have all the charm in the world and the best questions, but the male brain won’t accept you. If it feels that everything is orchestrated, your man will be more hesitant. Men naturally hate organizing and order, so it’s good to be spontaneous.

And what better way to be spontaneous than by throwing in some super random questions? These questions are quick and also open up a lot of subjects to elaborate on further. You can find out quick facts about your man and let him get to know you at the same time.

• Chicken or beef? What’s your favorite way of preparing it? (Unless he’s vegan or vegetarian)
• If you could live either in a place with permanent winter or permanent summer, which one would you choose? How long do you think you could hold up?
• Do you ever think paper books will die out?
• Marvel or DC? What would happen if Spiderman belonged to DC and Superman to Marvel?
• Did you know that there is a version of a Superman comic where he lands in Soviet Russia instead of Kentucky?
• Did you ever get drunk in a foreign country and got lost?
• What are the disadvantages of shopping online?
• What’s the last song you listened on Spotify/iTunes?
• What do you think about male-female friendships?
• Do you have a favorite documentary?
• What good things did Hitler do?
• Bananas or apples?
• Do you like crosswords?
• What word do you hate the sound of?
• What word sounds sexy to you?
• Dostoyevski or Tolstoy?
• One Direction or Justin Bieber?
• Florida or New York?
• Would you rather live in the countryside or in a city?
• What’s the tastiest fish you’ve ever tried?

This is the learning phase of your relationship. It’s of the utmost importance that you listen to your man. Even if you think basketball is boring and you can’t stand it, you can use that info in some time. For example, how happy would he be that you’ve reminded him that the Lakers are playing tonight? Ecstatic, that’s right.

You’re not kids anymore and every person values when they’re being listened to. Y our man is no exception. Both of you will enjoy talking about your passions, interests, and experiences. It’s important to have differing tastes and opinions. We would be bored to death by someone who resembles us too closely.

Pick your questions carefully. The more detailed they are, the more you will find out about the man sitting across the table. If something goes wrong, you can use questions like these as atmosphere relaxers and ice-breakers.

Personal Questions To Ask A Guy

We’ve arrived in the riskiest territory of them all – the personal questions. Such inquiries may end up spelling disaster if you ask them too soon. Make sure you’ve already developed a bond and that you have a healthy level of communication. Things like this mean a lot to people and every man can feel threatened if you inquire too soon or too “violently”.

You first have to establish a certain level of trust. Men are especially shy about personal info, especially around the opposite sex. By coming off as open-minded and committed to sharing your part of the story, your man will feel that he has shared as much as you. Equality and trust are the key. Don’t share too much, leave something for the future. The bond will grow on.

• Were your parents religious? How did that affect you? Did your outlook on religion change or not? Why?
• What’s your view on religious differences?
• Do you believe in a higher power?
• Long-term relationships or causal flings?
• Did you want to have kids when you were a kid yourself? How about now? How many?
• Are both parents equal in a marriage? Should both be the breadwinner or should the duties be split?
• Would you like to be a stay-at-home dad?
• Is your career something you would want to do forever or is it something temporary?
• Is marriage an important institution or just a piece of paper?
• What thing do you want to avoid when being a parent?
• What character trait do you resent the most in people?
• What character trait do you love the most in people?
• Could you be a single parent?
• Did you ever suspect you were gay?
• What thing do you regret the most in life?
• Do you think gay people should adopt?
• Should the church pay taxes?
• Is taxation theft?
• Do you think you could be with someone who is deeply religious?
• What sickens you the most?

These are important questions that should always be asked. The timing is also important. If you ask them too soon, he might get spooked and think you’re overly attached. If you ask them too late, you might end up in a relationship that doesn’t suit you. While you’re ready to settle down, he may be not. The only way to let him know is to ask him and let him tell you first.

No matter how unbelievable or dreamy he is, we are standing firm in reality. If it doesn’t function along the crucial lines of beliefs, children, and family – it’s bound to be short-lived. By asking him these things, you might fall in love even more or you will spare him and yourself the time. You can do it. Just be patient and don’t interrogate him.

Awkward questions to ask a guy

Relationships are not artificial; they are a living, breathing entity. If we view them as such, we have to acknowledge even the most embarrassing moments ever. They’re an integral point of every person’s past, present and future. That’s what this set of questions is – a barrier breaker. You should use them to lighten the atmosphere, once you’ve grown close to each other.

Awkwardness never has the same significance. In the beginning, it’s more of a weird breach of the atmosphere. You can make him freak out and abandon ship if you go too fast. Awkwardness later, however, is a whole different story. Then, it plays the role of a “bonding agent”, metaphorically of course. By seeing that both of you have awkward moments, you will feel closer and more human with each other.

• Did you ever pass out in a public place?
• What’s the worst place you’ve ever vomited in?
• When was the last time you peed your pants?
• If technology advances, would you try and give birth, if that became possible?
• What was the funniest thing to ever happen to you during sex?
• What would your mom say about you right now?
• What’s the funniest thing you ever did while drunk?
• Did you ever fall asleep during sex?
• What was the worst situation you ever laughed in?
• What is the stupidest situation you almost got killed in?
• How much do you think you could hold on without peeing?
• What is your most embarrassing dream?
• Did you ever get so drunk that you shat your pants?
• Do you have any embarrassing pictures of yourself?
• What was the worst situation you were ever naked in?
• Did you ever got caught skipping classes?
• What is your funniest fear?
• What was your worst Freudian Lapse?
• What’s the worst pun you know?
• What’s the best pun you know?

Never ask a guy the following questions

You often read in magazines how guys should be careful when asking girls certain questions and how men are much less sensitive. When talking to your man, you have to erase that completely. Men are more sensitive, if you didn’t know. That sensitivity comes from the fact that male emotions aren’t looked at so normally in society. Even today, it can be a problem for men to express emotion.

Asking a man about things like his size, if he works out, why doesn’t he workout, how tall is he, how much money he has is a big no-no. Male insecurities are better hidden than female ones, but much more fragile. If he shares some of this info with you, feel honored. If not, don’t ask any of these questions.

• How much do you make exactly?
• Did you have problems because of the size of your friend down there?
• Do you work out?
• Why don’t you workout?
• How tall are you?

Questions like these are reserved for more intimate relationships. Men are shackled by social expectations. They have to be taller than their woman, they have to make more, they have to be fit. Sometimes, asking them such questions will touch on their deepest insecurities.

These are all expectations and social customs that should have died a long time ago. If you’re taller than him, don’t mention it right away. If you see he isn’t that fit, it’s okay! Motivate him to work out with you, instead of being so blunt. There is a thin line between caring and hurting. Sometimes, caring can be wrongfully interpreted.

Questions To Ask A Guy You Like…..Conclusion

Speaking to the guy you adore can be a daunting task. It isn’t. It can only be daunting if we present it like that in our minds. Our nervousness comes from the fear of failure. It doesn’t have to persist anymore. Relax! Nothing will probably go to plan, but that’s just the beauty of talking to your dream guy. Treading into the unknown.

The truth is – he’s feeling as nervous as you, and even more! It’s just that guys don’t show it that much. Have courage and don’t be afraid to let him know you care and that you want to know him from top to bottom. There are conversation ruts and you shouldn’t overthink when they happen. Pop a simple question like “How was your day today/yesterday”. Such a move might save conversation and the next thing you know, you might find yourself with a ring on your finger, in a house with him, two kids and a big dog.

In A Nutshell: Final Tips

• Relax and don’t view it as a life-or-death situation. The priority is to let him know the real you.
• Communication is not only about words. You can fake what you talk, but not your body language. Again, relax and be open and kind to him.
• Don’t ask specific questions too soon. Instead, don’t lean on these questions at all. Let the conversation flow and you might not even need them. Take them more as an instruction manual, not a Bible!
• Equality. Maintain equality. As much as he shares, share the same amount of info or just a little bit more. That little bit more might motivate him to share even more, too. Don’t overdo that amount or it will seem like you’re only bragging about yourself.
• Keep the relationship questions ready, but only when you’re sure that the date is going in that direction. Too soon and you might spook the poor fellow.
• Be flirty and funny, he will appreciate it. Sexual comments are only appropriate in the appropriate situation.
• Deepen the differences. The more different interests you have, the more interesting the conversation will be.
• The beginning is always the scariest part. Once you’re over the hump, everything should go smooth. Good luck and have fun!