Lesson 1 - Muck the wish list.

Dealbreakers - you know you got ‘em.

They're the invisible checklist you carry into every date, non-negotiables that make a relationship impossible.

As professional cupids, we’ve witnessed all kinds of client preferences. Men come in with a long list of ‘wants’. From ‘long red hair’ to ‘must like pineapple on pizza’, nothing is off the table.

But let's be real. As experts, we understand that these aren’t the things that lead to a happily ever after. And we’ve mastered the art of reading between the lines.

In order to do that, we focus beyond the wish list. Here’s what we mean.

Wish list: These are your likes and dislikes that can change or evolve over time (hair color, height, hobbies, interests and even passions). These can certainly contribute to attraction and enjoyment in a relationship, but they aren't as crucial for long-term compatibility.

What really matters: Your core values that guide your actions (such as honesty, loyalty, and independence), and your long term goals (wanting children, retirement vision, travelling 6 months a year). These are elements of a person's life that tend not to change much over time and can significantly impact the compatibility and longevity of a relationship.

Now, you know the saying - "opposites attract"? We've found it to be true more often than you'd think. Differences can enrich your relationship, presenting both of you with fresh, exciting experiences.

In other words, it’s not about having matching hiking boots, cooking aprons, or even diets, it's about having a shared level of respect and curiosity that leads to mutual growth.

Don’t forget, not sharing the exact same lifestyle doesn’t mean there isn’t a plethora of things to still bond over, for example:

✅ Exploring new ideas and philosophies about the world.
✅ Doing Sunday chores while listening to different podcasts.
✅ Learning from each other's unique views and perspectives.
✅ Discussing the latest articles you've read, even on varying topics.

It’s important to keep in mind that a lot of this will only surface after the first date. Hence, the importance of mucking the list and keeping your mind open!

Lesson 2 - Double down on the video date.

It’s typical to go straight from texting on a dating app right to an in-person date. It’s no wonder you might feel like you're spinning a roulette wheel, never quite sure where the ball will land.

Often, you leave your dates feeling frustrated, disappointed with how much time you spent, and discouraged by having to start all over again.

Let us let you in on a little matchmaking secret: We set up our clients to meet on video first!

Since the pandemic, there's been an incredible rise in video dating, and we're here for it. This simple step allows you to see if there’s enough chemistry and mutual excitement to invest your valuable time into a real first date.

So if you’re meeting most of your dates online, a quick FaceTime before meeting grabbing a drink together can be a smart move.

How to set it up: The key is for her to know exactly what she can expect, so we suggest painting a picture for her and keeping the ‘date’ short.

Here are some examples of what to text her:

💬 “Hey, it’s been nice chatting with you. I’ll be going for a short walk with my pup around 7PM, wanna hop on FaceTime and meet him? :)“

Or…

💬 “I’m just about to pour a glass of wine before heading out with the boys in a bit. Wanna hop on FaceTime for a quick chat? :)”

Transparency is the name of game. If you sense she’s hesitant, be upfront. You can say something like:

💬 “Just wanna make sure you think I'm as charming in real life as I am in text 🙈 But for real, I know we both have busy schedules, a quick call is a nice way to get to know each other a bit better before planning our first date. What do you say?”

Of course, this doesn’t replace a first date. It's a sneak peek, a chance to see if the curiosity extends beyond texting on an app.

And if so? Great - You can head into a real date with more confidence. If not, you've saved both of you precious time and energy. This also means every actual date you do go on has a higher chance of being a hit. It’s a win-win for everyone.

Lesson 3 - Don't gamble on conversation.

As matchmakers, we get to hear all about what went down on your dates, and let's just say it's a unique privilege!

You might think ‘what to talk about’ is a non-issue. If only you knew the stories we've heard! From a man who literally read off a script, to a detailed how-to on taxidermy (yes, it's happened).

Here’s some pointers for ya:

One great resource to use is her dating profile. If you met online, review her profile before your date, it can be a treasure trove of useful conversation starters to keep in your back pocket.

In terms of questions, we suggest using a mix of Broad and Detailed.

Broad questions like "How was your day at work?", "How has your week been so far?" or "What are your plans this weekend?" feel natural and often offer several threads to pull at, making it easy for you to build upon the conversation.

Detailed questions, on the other hand, are like a first date cocktail - they add just the right amount of kick to keep things lively.

Here are some examples:

🍸  "What's a recent [book, movie, podcast, documentary] that changed your view on something?" — This gives you insight into her intellectual interests and opens up the possibility for a deeper, more meaningful exchange.

🍸 "What's the top destination on your bucket list, how did it make it to the list?" — You can dive into an exciting conversation about travel experiences and aspirations.

🍸 "What's a passion project or hobby that you're excited about right now?" — It allows her to share something she’s passionate about, giving you a closer look at what she enjoys outside her everyday routine.

Also, try to make it a habit of saving the things you have most in common to bond over during your first date (versus exhausting them beforehand, which can be tempting to keep the connection alive).

Lastly, when all else fails, talk about something you’re personally passionate about! (As long as it’s not taxidermy, LOL).

[🎰 Bonus Spin!] Lesson 4 - Fold on these topics.

On that all-important first date, it's easy for something to be misinterpreted (or seen as a red flag ) until you've had the chance to get to know each other.

Here's a quick list of topics to avoid:

1. 🚩 Exes: Steer clear of this topic as it might suggest you're still living in the past.

2. 🚩 Politics and Religion: These subjects can trigger disagreements on a first date. Best saved for later.

3. 🚩 Negative Personal Stories: Sharing these can bring down the mood. Aim for an upbeat, positive atmosphere.

4. 🚩 Financial Matters: Talking money too soon might be seen as bragging or complaining, neither of which are first date friendly.

5. 🚩 Criticizing Others: This can give an impression that you're a negative person. Keep the focus on positive topics.

6. 🚩 Over-Complimenting Physical Appearance: Overdoing this can make your date uncomfortable and suggest you're only interested in physical attributes.