The Awkward Guide to First Dates (2024)

4 minutes read –

The first date. The mere mention of the word is enough to send even the bravest souls quivering into their tea. How does one traverse the minefield of first date faux pas and lead the conversation to that coveted second meetup?

It’s a time for nerves, excitement, and maybe a little bit of awkwardness. You’re meeting someone new, trying to make a connection, and hopefully having a great time in the process. But what should you talk about? What topics are safe and interesting?

Be yourself and let your light shine. First dates are usually awkward, but they do not have to be boring. Embrace the nervousness, own the awkwardness and accept that you are not two perfect robots on a date, you are two imperfect humans. And after all, that’s what makes it interesting, right?

We tend to think of a date as a bit of a failure when romantic sparks aren’t flying. I encourage you to flip the narrative. What if, instead, we started to get really excited about simply connecting with another human in the world?

We are all here for a short time and have so much to learn from each other – what an honor it is to share space with another human being and the journey that led them to this very moment. When we view dating simply as an opportunity to connect with people that we wouldn’t otherwise, we win every single time.

Remain curious and let go of all expectations. Aim for a balanced conversation with a little bit of sharing and a little bit of listening. Remember, this is not an interview – this is a time to notice how you feel around each other and if you are curious to learn more.

The key here is to find a balance between light-hearted and meaningful. You want to avoid the cliché small talk that can leave you feeling disconnected, forget the superficial questions about hobbies and career. You want to dive into the deep end of who you are at your quirky core but you also don’t want to dive straight into your deepest fears and insecurities. Following are a few conversation prompts that will help you strike that balance and get the authenticity flowing:

• Tell me about a time when you felt truly alive – This is a great question to start with, as it invites your date to share something meaningful and personal, without being too heavy. It also gives you insight into their passions and values.


• What’s something you’ve been curious about lately? – Curiosity is a great trait to have, and it can lead to some fascinating conversations. This question also allows for a wide range of answers, from scientific discoveries to personal interests.


• If you could instantly become an expert in one subject, what would it be? – The yearning to gain proficiency in particle physics or 16th century lute compositions shows a curious mind (or one prone to useless yet amusing talents). Both bode well for an engaging date.


• What’s a challenge you’ve faced recently, and how did you overcome it? – This question shows that you’re interested in your date’s life beyond the surface level. It also gives them the opportunity to share their resilience and problem-solving skills.


• What’s something you’re currently struggling with? – This question requires a bit more vulnerability, but it can lead to some powerful connections. It’s important to approach this question with empathy and without judgment.


• Tell me about a place that holds special meaning for you. – This question invites your date to share a personal story or memory, which can be a great way to build intimacy. It can also reveal a lot about their values and priorities.


• What inconvenience do you find utterly unacceptable? – Strong views on poor tea selection, mismatched socks or unexpected space-time continuum ruptures display the intensity of your pet peeves. Bond over mutual vexations with the universe.


• What have you always believed to be true that most people would disagree with? Sharing quasi-conspiratorial or controversially optimistic views of life shows an independent spirit not swayed by the mainstream. Just take care not to don a tinfoil hat unless specifically requested.


• What’s your least favorite smell? – The odors one dislikes reveal much about the smells one enjoys. A fondness for patchouli oil or freshly mown lawns could be delightfully compatible or prompt a quick excuse to exit the premises. Take a chance!



• What lesson did you learn the hard way? – Discussing a time your poor judgment led down a path of embarrassment and frustration displays humility, wit and the ability to laugh at yourself. All desirable qualities in a potential partner prone to leaping before looking.

Of course, these are just a few examples. The key is to listen actively and respond authentically. Don’t be afraid to share your own experiences and opinions, but also be respectful of your date’s boundaries and feelings. It takes practice and vulnerability, but the rewards are worth it.

A first date is all about finding a balance between light-hearted and meaningful conversation. By asking thoughtful questions and listening with an open heart, you can create a space for deep and meaningful connections.

On a first date, avoid discussing your dating history and exes. Nothing kills the mood faster than hearing how your date’s last partner was “crazy and clingy” or yelling obscenities under their window at 3 AM. Nobody needs to know about your disastrous attempts at online dating or how many matches it took your Aunt Edna to set you up before you finally agreed to meet someone “normal” for once. Dredging up romantic emotional baggage and dating war stories should be avoided on a first date as aggressively as cheap cologne and visible panty lines. Some things are better left unsaid, at least until the second or third date!

In conclusion, first dates can be fun and enlivening. If you’re looking for more personalized recommendations or advice on that big first date, consider reaching out to Sophy Love. As a professional matchmaker and dating coach, Sophy Love can help you not only prepare for a first date or process how it went but also create a truly special and memorable experience for you and your partner. Whether it’s a first date or a special anniversary, Sophy’s executive matchmaking services can provide you with the guidance and support you need to make your evening unforgettable.