Phone dating can be a blast when two partners engage in deep, meaningful conversation. Whether you are on a chat line because you are into a flirty friendship, or you’re on the line to meet that special someone who you might someday marry, you are going to want your chat line conversation to be very interesting. Otherwise, why are you on the line? We don’t recommend stepping into a chat line conversation completely blind, as in not prepared with questions. Why? Well, questions are what drive interesting conversation. Without them, there’s a ton of awkwardness. You’ve been there before, right?
If you’re someone who has spent a significant amount of time chat line dating, you’ve almost definitely experienced that awkward chat line date where silence fills the ‘conversation’ more than actual words do. It could have been because your date was super quiet and awkward, but it might also have been because you weren’t asking the right questions! And, who knows? Maybe that quiet awkward match just needed some nudging to open up and blow you away! We don’t want you missing any more opportunities. Moreover, we don’t want you to have any more boring conversations. Check out our list of meaningful questions that you can keep on deck for your next chat line date!
First, before we even get into the questions, we should probably mention that phone demeanor also has quite a bit to do with how a conversation can go. For example, if you come off as judgmental or mean towards your chat line date, what makes you think that she is going to open up? You’re going to want to make sure that when you call a chat line, you act and sound like a gentleman so that the chit chat can run smoothly. What does this mean exactly? Well, we will tell you! Make sure your voice is both calm and inviting rather than pushy or slimy. There are lots of seedy guys who call into a chat line, don’t be one of them! More than that, you don’t want to insult any of her answers to her questions. Keep your conversation a safe zone for her, so that she can truly open up to you and start something really special.
For people looking for a serious relationship
Again, there are several reasons why someone might call a chat line number. Most often, it’s because people are looking for a romantic connection. Those looking for someone to spend their lives with are going to want to ask deeper questions than those just looking to flirt or make some local friends. Because you’re trying to find someone to potentially walk down the aisle with, you are going to want to steer the phone chat in a serious direction. You can do this without coming across as someone who is desperate. There’s a way to make deep questions come off as both meaningful and lighthearted, because women don’t call a chat line to be quizzed or feel as if they are being put on the spot. After all, this is only a first date technically. You don’t want to scare someone off who could potentially be your lifelong match. If you are truly looking for a significant other, here are the questions that we suggest for you…
What are you looking for in a serious relationship?
What are your favorite qualities in a man?
Do you have or do you want kids?
When was your last serious relationship?
Are you a religious/spiritual person?
Are you someone who likes to go out and party or stay in and snuggle?
Are you an introvert or an extrovert?
Are you close with your family?
Are you a native of the area or did you move here recently?
Do you want to raise a family here?
What is your best friend like?
Are you someone who has many close friends or a few best friends?
What is your favorite way to spend the day?
What do you do for work?
What are you passionate about?
What are you most grateful for in your life?
What is something you do to relax?
Have you ever had your heart broken?
Have you ever broken someone’s heart?
What are the things on your bucket list?
Do you like to travel?
Where is your favorite place that you’ve ever traveled to?
Do you have any regrets in life?
What are your biggest fears?
How many times have you been in love?
Do you believe in soulmates?
What is your biggest pet peeve?
These are of course very deep questions that will provide equally deep answers. You should always be prepared for any of those questions to be flipped back onto you, and you should have a great answer ready. Answer honestly and openly, and in the same breath, respect her answers. If you are going to pry deeply, you are going to have to do so respectfully. There’s so much information that you can gather from these phone dating questions, but if you are looking for something a little less serious (like flirting or friendship), you should perhaps ask questions that are still interesting and fun, but don’t employ such revealing answers.
Here are our favorite among these questions and why:
“What are you looking for in a serious relationship” Asking this question in the first place will show your chat line date exactly what you are looking for by calling into a phone dating service, but it will also allow you to discover what she is seeking and if you can deliver on those things that she is looking for in a relationship. At The Big Fling, we always suggest being your truest self when talking on a chat line; however, knowing and fitting the mold of what someone wants in a relationship is never a bad thing, and it’s always good to have that knowledge on your side.
“Are you a religious/spiritual person?” Never underestimate the importance of religion to the survivability of a relationship. Even if you aren’t religious, you are going to want to make sure that you aren’t wasting your time with someone who could never truly fall for you because she is very religious. There are of course religious chat lines that you can call if you do lean one way, but if you are open to allowing other spiritual practices in your life, ask this question to make sure that you aren’t wasting any of your valuable time.
“Have you ever broken someone’s heart?” When you ask this question, you’ll get a sense of what you are in for with the woman you are speaking to over the phone. If she answers that she’s never been a heartbreaker, you know you have a sweetheart on your hands. However, if she has broken a few hearts, the way she speaks about it will reveal a lot about who she is as a person and if you should or shouldn’t keep your guard up.
For flirtation or friendship
The questions you ask on a chatline date that are for flirtation or friendship can be a bit more colorful than the above questions. They can be more silly, but beware that the implication of the relationship you intend on having might come off as more frivolous. You’ll come across as a fun-loving guy who is a great conversationalist rather than someone looking for a wife, which might be exactly what you need. If you aren’t sure (again, also very fine), you can mix it up between these questions and the above, more serious, ones. Here are some questions for you to ask that will be fun to answer but provide a space in which you’ll be able to learn a lot about your chat line date from her answers!
If you were stuck on a desert island, what 3 items would you bring?
What your favorite movie?
What type of music do you like to listen to?
What’s the first thing you’d do if you won the lottery?
What’s the craziest adventure you’ve ever been on?
What was your first kiss like?
What people, alive or dead, would you invite to a fantasy dinner?
What is your version of paradise?
Have you ever experimented with substances?
Who is your favorite animated character in TV or movies and why?
Have you ever gone skydiving or would you?
What is your favorite place in the world?
What movie do you watch over and over again?
What embarrassing song do you sing when nobody is listening?
What’s a weird talent that you have?
What job did you want to have as a kid?
What is your favorite restaurant?
Who is your celebrity crush?
What’s your most used app on your phone?
Are you a morning person or an evening person?
When’s the last time you pulled an all-nighter?
What was your college experience like?
What’s your most embarrassing moment?
Salty or sweet?
What’s your weirdest sexual fantasy?
Would you rather have the power to be invisible or fly?
Here are our favorite among these questions and why:
“What people, alive or dead, would you invite to a fantasy dinner?” This is an awesome thing to ask because it’s really fun to answer, but it also tells you a lot about the person on the other end of the phone. What people do they value the most? Are they mostly celebrities or intellectuals?
“What’s your most used app on your phone?” A person’s phone will tell you a lot about them, especially when it comes to the apps that she uses the most. For lots of women, their apps range from shopping apps, to workout apps, to social media and so on. When she tells you which ones she uses the most, you’ll be able to deduce what her interests are and play off of them in a future conversation.
“Would you rather have the power to be invisible or fly?” This question may seem innocent, but it’s actually quite philosophical. Think about it, why would someone want to be invisible? There are tons of reasons, but most of the time it’s to be able to be a fly on the wall in many situations. Flying, however, is mostly desirable for the thrill. So, are you talking to someone who values intellectual or mysterious power or someone who is an adrenaline junkie?
When the questions are turned on you
As we’ve said, and you can probably guess, when you ask your chat line partner to answer these revealing questions, they are going to be turned on you. Before they are, make sure to acknowledge her answers with an open mind. It’s ok to be flirty and poke some fun, but never make anyone feel bad about themselves or their answers, there’s a very minuscule chance they called into the chat line to be ridiculed. When you answer, be as honest as possible without scaring her off. You can use her answers as a way to get to know her and see if you are a good fit, but at The Big Fling, we don’t believe you should be manipulative with your answers because you want the right girl to want to chat with the real you, not the person you’ve invented based on her answers.
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