Two On An Island challenges you to keep building your romantic agility. It's a game where surprising and delighting your mate earns you fame and glory. Join by accepting our INVITATION


These seven Challenges are a Pursuit Of Passion. When you accept our FOOD CHALLENGE, you're asked to tell a story of how you tantalized your mate's palette - we will guide you, let's create culinary magic.

With the SPONTANEITY CHALLENGE you will be like a Jedi knight, your advanced mind technics and astonishing attentiveness will shock some.


We made it easy, we call it Reverse Follow. Once you've decided to PLAY, Simply post on Instagram using #TwoOnAnIsland.  We are truly proud of the real life, heartfelt Love Stories our islanders 'from around the world' share on Two On An Island everyday.


Those who Win at Love & Romance, Win at Life arrrr mateys!

If you were born to cheat at Love, then you were born to cheat at Life. 



This challenge is for the people on both side of the bed. Play together if you like. DARE each other, post stories of memorable romance. Put your plans into place and seduce your mate when you're free on the weekend!


During the Challenge, your TOAI team will provide tactical guidance and tips. Then it is up to you to prove your skill. Use the clues and ideas included in your Romance Planner's messages to seduce your mate.


To earn the right to be called ISLAND WARRIORS you need to complete seven distinct Two On An Island Challenges and post your accomplishments on Instagram (#TwoOnAnIsland).  We think of ISLAND WARRIORS as “Expert Lovers". Warriors proudly display their Challenge Badges and tell their stories. Accepting this Challenge is like fine tuning Advanced Romantic Skills.


At Two On An Island our job is to initiate romance and as it happens, narrate your Love stories. We call it reverse follow, because once you become a member - we will follow you! That way as you do our weekly Challenges, we will check-in occasionally to see how you're progressing on the island.


Need some inspiration? Follow our Instagram Stories we've set out to inspire your sense of passion by featuring the best of Two On An Island in short entertaining romance stories. We cannot wait to tell you about the upcoming Magazine!

WHY play

Our success is tied to your success, the number of couples we keep determines our worth. Therefore we think you should play because we will do whatever it takes to coach you in the proper keep and care of your Love. That's our priority number one.


Two On An Island form affinity for various groups, we call them Tribes. tribes are like sub-groups within Two On An Island. We give our Tribes exotic island domains such as ARUBA or TUVALU. To help you get settled into your Tribe, a Romance Planner is only a question away.


Coming soon, it's gonna be good!


Sponsorship is important to us. To start we spend much more than we earn for our services, we are setting the bar high right at the start. Interested in sponsoring us, we're looking for companies whose products and mission is aligned with ours.


That's cool - no worries mon! - whenever you find someone worthy of your love, your efforts and your romance, come back to the Island, the doors are open, come in - you're always welcomed!


Playing the Romance Games tests growth in passion. We focus on small ideas one week at a time. Another way we use small batches is in the size of our Challenge cohort /player group. Currently we are only able to attend to 200 islander couples.


We're gone to the islands soon come back, our little island shop will be filled with nuff nuff stock. T-shirts, Frocks, Paintings, Button, Stickers; things like that. All made with hands from the islands mon. See the sun, the waves, feel the breeze and the sand, we'll find little treasures just for you & your companion!!


Two On An Island is meant to help you keep your Love fresh. We respect each others opinions and we hold privacy sacred. We welcome anyone striving to keep their Romance alive and well. Thank you for trusting us, we are working with Squarespace and other services to secure your privacy.


We hope your aim is to become the most passionate, romantic & alluring lover imaginable. If you are, Two On An island is just what you need. To show our thanks one couple every Challenge will get a chance to visit an actual Caribbean island, all on us.