A couple sharing a fun and exciting first date with ice cream

Unlocking the Secrets to Fun and Successful First Dates

By Published On: March 27, 2024

How many times have you found yourself in this scenario: You are meeting a potential romantic connection for the first time and you decide to go to a restaurant… because isn’t that what we do on first dates?

You awkwardly try to determine if a hug or handshake is appropriate and then wait to be seated. Sitting across from each other, but unsure of where to look or how often to make eye contact. Finally, you find a topic that you can both relate to but then the waitstaff comes around and offers you beverages. The conversation loses its momentum, you are finding it difficult to keep the conversation going as the server keeps interrupting you. Why on earth did we have to get such an attentive server?!

Have you ever wondered if there is a better way to navigate early dating? Have you ever wondered if you could bond with a new person better in a different setting? As a Certified Dating and Relationship Coach, I help my clients to have more fun and success in their dating journeys.

In this article, I am going to share some of the best first-date locations from personal and client experience.


Ladies and gentlemen, get your walking shoes on!

We tend to think of first dates as a time to get all dressed up and present this ideal version of ourselves. In reality, it is about getting out there and seeing if you enjoy spending time with this person and finding ways to form a bond. Finding a scenic route that is well-traveled can make for a great first date. The activity allows the conversation to flow more easily without all the pressure of eye contact.

Ideally, you can walk where there are places to stop and sit so that you can enjoy light eye contact at points during your time together. Consider starting with a walk and if it is going well end at a casual eatery or grab a beverage together.


As previously mentioned, a nice dinner can create a lot of additional interruptions and pressure, as well as feeling hostage to the check if the date is not going well. Opt for something more casual that can be ordered and picked up at a counter and find a nice spot to sit and eat or drink where you can sit side-by-side instead of facing each other.

Ice cream or any kind of dessert can make it feel like a special occasion. Food trucks can still be high-end without being so stuffy and they are typically in an environment that allows for a more relaxed first meeting. If you are in a hot region look for indoor food halls/markets that have high-end food with a more casual vibe and lots of counter seating.


Going somewhere that has natural conversation starters can be a great way to get to know someone and how they navigate the world. Go to an art gallery and learn about how a person thinks about abstract things like art, do they see beauty everywhere or are they picking apart and criticizing the artwork? Go to a museum and see what they gravitate towards, if there are exhibits to interact with, allow yourself to play and be silly if that is a part of your personality. If the person thinks you are lame or weird maybe that is not the right person for you!

Do you have a strong desire to help and give back? Suggest volunteering together for a first date, if that is something they are passionate about you will likely find you have much more in common than that!

Thrift store or antique shopping can bring up fun conversations that will give you a peek into who this person is. Meet each other at a bookstore and discover what reads you have in common. If you feel comfortable you can even do a scavenger hunt.


Activities are a great way to build rapport with a new person. Try axe throwing, bowling, miniature golfing, bike riding (as long as you can still talk and hear each other), shooting some pool, or challenging each other to games at an arcade. 

If you opt to go to a coffee shop, winery or brewery look for places where you can play games together or even consider bringing your own game to play together. Comedy can also be a fun date although you will want to follow it up with a beverage so you can discuss what you like or didn’t like about the Comedians.


Trivia can be a great way to work together and see what kinds of things your date is most knowledgeable about. An escape room will allow you to see how they react under pressure and how competitive they are, then follow it up with a beverage so you can talk about your experience together. 

First dates don’t have to be stale or boring.

Consider ditching the typical restaurant or bar and try breathing new life into your dating journey. Whether you get out and walk, get creative with casual dining, discover new things together, get playful, or problem-solve as a team, consider picking a few options to present to a date so they have some things to choose from. If they are excited about one of the choices you suggest you may already have that in common or it may empower your date to make a suggestion or two of their own.

If you find that you are experiencing burnout and are in need of a mindset shift, consider working with me as your coach. I specialize in shifting your mindset and confidence so that dating can be an enjoyable and empowering experience.

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Written by : Lisa Gunnett

Since childhood, I've been a storyteller, crafting tales accompanied by illustrations, a habit instilled by my mother. Now, through my writing, I aim to shed light on both common and uncommon challenges in dating and relationships. My mission is to provide insights that empower individuals to heal themselves and navigate healthier, more fulfilling connections. Join me on this journey of discovery and growth!

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