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As a matchmaker for almost a decade, I am honored to have matched more than 2,000 singles and set up more than 700 dates in my career.
But despite the number of dates I’ve planned, I would be lying if I said that all the dates had happy endings. Truth be told, I’ve worked with a number of singles who really know how to botch the first encounter.
We can all agree sometimes the first-date jitters get to us, and we may say things on the first encounter that we regret later. But some date feedback I’ll receive from time to time never fails to take me by surprise.
You would think that, when it comes to first dates and first impressions, you can’t go wrong. Oh, but you can. Whether it’s ego, narcissism, high/low expectations, or an extreme case of nervousness, daters sure know how to ask the wrong questions. That’s where I come in. As a Certified Love Professional, it’s my job to introduce you to quality singles and guide you through the dating process with value and authenticity.
The following 15 questions in this article will help get you on track to having a lovely experience on your first date. Start with Question #1 through #7 for icebreakers and look to Question #8 for deep diving into the more serious conversations. Follow along and allow me, your Gay Fairy God-Matchmaker, to suggest great conversation starters.
This question may not be the most exciting or intriguing one to get the conversation going, but you have to start somewhere. Whether on a first date in person or meeting on video chat on Match.com, you have to start with the basics to help the conversation along.
Although the question may present itself as basic at first glance, your anticipation for their answer will keep you excited. This question will allow your date to open the floor to who they are, where they’re from, and what they like. And it can guide where you want the conversation to go.
Once you’re introduced to a person’s background, a great follow-up question is to learn about your date’s hobbies and interests.
Growing up in one of the best metropolitan cities in the world, Los Angeles, there’s never a dull moment. Everyone has a leisure activity they like to do in their spare time whether it’s a sport or other physical activity or just laying low and diving into the world of literature, arts, or music.
Relating to the same hobby and interest you have with your match not only furthers the conversation, but also potentially creates positive qualities you may have about your match once the date has been completed.
The date is just getting started and one of the best ways to channel a person’s inner, child-like thinking is to divert to this simple anecdotal question:
TV Show, Film, Superhero, Supervillian, Season, Food, Go-To Beverage, Music, Way To Stay Active, Hiking Trail, or fill in the blank with something you’d like to know.
Let’s face it, small talk is boring. But one way to get a glimpse of someone through their eyes is with straightforward, open-ended questions.
The, “What’s your favorite” will allow you not only to create conversation, it could help you find out more about them than you expected. Their answers should be accepted for better or for worse, agree to disagree, but in a fun, relaxed environment where it’s not supposed to be taken seriously.
To switch things up, you can even change up the question and pace.
Where am I going with this? Hear me out: A fun, icebreaking version of “Would You Rather” will allow both daters to agree to disagree in a fun, relaxed environment.
And why? Once again, straightforward, but open-ended questions that will force your match to explain their thought process.
Although asking all these fun questions can really get the date going on a positive note, you need to make an interesting impression that will differentiate you from others and really dive deep into the person’s background and prompt more thought-provoking questions.
Switching up from fun icebreaker questions to fun thought-provoking analysis will really allow you to understand a person’s experience in life.
Regardless of how they answer, this question guarantees you an automatic response. If they answer the question, you can follow up with your own experience if you have partaken in that activity. Or you can allow them to explain in-depth why they want to try that activity.
If they can’t answer the question, it’ll allow you to take control of the question with your own experiences so they can get to know a little more about you.
Speaking of new-city experiences, the next question really dictates a person’s experience with new life and cultures:
Whether domestic or internationally, questions regarding travel will enable you to share travel stories, open up about what they experience, discover any hidden gems they’re willing to share, and whether they recommend the experience.
Not only that, the topic of travel also allows you and your date to imagine ideal types of vacation destinations and travel spots they would like to check off the list.
Fun fact: Author Richard Wiseman, in his book titled, “Quirkology: How We Discover the Big Truths in Small Things,” found that 18% of daters said they wanted to see their match again when the topic of travel came up.
Not only can the topic of travel bring fascinating conversation with your match, this topic can bring up interesting debate.
In today’s modern world of streaming platforms, we are exposed to different outlets for films, shows, and media, including Netflix, Hulu, Amazon Prime, YouTube TV, and Spectrum. Even those who aren’t regular subscribers of these outlets will have a favorite show that holds a special place in their heart.
It’s entertaining to talk about the different franchises or series you’re watching, dish on must-see movies of the year, and reveal to your match your hot take on a show or films that didn’t hit the mark. This will allow the conversation to flow naturally while you and your date reveal more about your respective personalities based on what you both watch.
Now that you are starting to build rapport with your match, you can ask the thought-provoking questions that will allow you to get to the bottom (and not that bottom) of someone’s character and dating purpose.
A man with a plan is a man we want to see again and again. To shift gears, ask the next eight questions:
It sounds scary and way too straightforward to ask on the date, but when you think about it, unless you’re being set up by a Matchmaker, you really don’t know a man’s dating intention if you meet him on a dating app or through mutual friends.
The sad reality is that, when it comes to gay dating apps, most men reach out to other men based on physical attractiveness and whether they’re guaranteed to have sex after the first date.
Where have all the men with valuable intentions gone? Although the man in front of you may be a good catch, you need to determine if he’s looking for his person or looking for a person in his bed by the end of the night.
And before you say it, no, you don’t need to bring up marriage, kids, religion, or politics. All you have to say is, “So, what are you looking for? I’m curious to know how someone like you is still single?” It’s simple, it’s flirtatious, but not too serious.
A man who has goals and inspirations he wants to check off his bucket list is always a keeper!
Whether the goals are simple or more involved, this shows that someone is goal-oriented and wants to experience life to the fullest.
This question has the same objective as the Bucket List question, but it shows you’re a man who seeks personal development and self-value for a better future.
Whether a man’s goals involve love or are related more to his career or financial aspirations,he has objectives that he wants to complete. And a man with a plan is always the type of guy we know is a diamond in the rough.
This will show a man’s purpose in life. A guy who lives life with a quote or mantra shows he has inspiration that must be fulfilled. Maybe he will surprise you by bringing up quotes like:
Such philosophies open the mind to understand truths and acknowledge things you otherwise would have missed.
A man with this mindset will allow you to see life from a wider perspective and, in this sense, expand your own awareness.
A man with passion reveals his courage. Very similar to the mantra a man lives by, this question can provide insight into how a man will treat you in a relationship, and how he lives his life.
A man who’s passionate will most likely contribute to greater fulfillment, not only when it comes to satisfaction both in and out of the bedroom, but also general well-being and relationship success.
A man who’s passionate cares about what’s meaningful to him. And if this guy who you’re on a date with allows himself to become vulnerable about his passions, quickly snatch him before someone else does!
I’m a firm believer that if lifestyle patterns don’t align, it’s not going to work in the long haul! Someone’s style, whether it’s carefree and without plans, will allow you to learn about his daily routine and if it can align with your own in a positive way.
Knowing whether your date is an early bird or a night owl, the life of the party or a homebody can save you from someone you’re not compatible with.
As scary as it may feel to ask your date about their life inspiration, this question separates men with purpose to boys who are still trying to figure their life out.
As a Professional Matchmaker for Gay Men, most of my clients want to be matched with men who have their act together.
A man with drive shows a man who is willing to go above and beyond when it comes to goals, aspirations, and seeking learning objectives.
How your date physically presents himself is not the whole story.
The truth of the matter is that the person in front of you is an absolute stranger, and you really don’t know who this person is or what he stands for.
In life, we may sometimes judge a person based on their cover. But you don’t truly know someone until you start to turn the pages on their book.
Asking this question will not only allow your match to self-assess himself, it will allow you to learn something about him that may or may not surprise you.
No matter how many dates you’ve been on, if you want to have fun on the first date and engage in conversation that will make your date memorable, you need to dig into your child-like curiosity and have an open mind when it comes to the dating process.
Dating is supposed to be a fun activity in which you get to meet someone new, with the potential that a first encounter can grow romantically.
As a Certified Love Professional, it’s my job not only to introduce you to quality singles, but guide you through a dating process with value and authenticity, and at the end of the day, first impressions MATTER.
You can never go wrong with the following 15 questions to have a lovely experience on your first date.I hope putting these 15 questions into practice will help you to date with purpose, but also have a fun experience meeting someone new.