It’s not a common sight to see a lone woman exploring Southeast Asia on her Harley-Davidson but Ride N’ Seek host Jaime Dempsey is paving the way and going places few tourists have ever been … in fact some may even be new to the locals themselves! My rad friends Persis and Raven from Tomboy Tarts , a revolutionary lifestyle site out of Southeast Asia that celebrates the tomboy spirit, caught up with Jamie to get us the insider scoop on her up coming adventures on season 2 of Ride N’ Seek. 

While other girls of her age were playing with dolls, Jaime Dempsey’s fondest childhood memory was sitting at the handlebars of her father’s motorbike as they rode out to get doughnuts. At the tender age of 5, she fell in love with the thrill and excitement of being on fast bike as the wind rushed past her.

Born in Illinois but raised in England, it’s no surprise that this bubbly American biker grew up with a love of biking and an appetite for adventure.  She took up riding about 8 years ago and has owned such bikes as a Yamaha XS650, Harley Iron 883, and a Ducati Monster 695.

When Asia came calling, Jaime flew halfway across the globe for the gig of a lifetime and rode across Peninsula Malaysia on her Harley Sportster Forty-Eight for the debut season of Ride N’ Seek. She is now into the fourth season hosting the show which will focus on her amazing bike trips around the Philippines.

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The fourth season of this motorcycle travel documentary is called Ride N Seek Philippines and Jaime will be on a quest to find the last remaining 96-year-old Kalinga tribal tattooist to get herself a tattoo from her before this art form dies forever.

For hundreds of years, the Kalinga tribe was feared as a tribe of savage head hunters. Central to their identity were their distinctive tattoos, separating the men from the boys, the elite from the average, protecting against sickness, injury and death.

To get there, she’ll bike across the island of Luzon. From jungle to mountains to beaches to active volcanos, Jaime will experience some of the best the Philippines has to offer.

Ride N’ Seek Philippines comprises of six episodes starting Monday, 18 July 2016 9:30pm (SIN/HK) on HISTORY™ and HISTORY HD™.

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Over the course of this latest season, you will get to see Philippines in a whole new way. Viewers can also expect this latest season of the show to be more physically challenging for Jaime as she travels off the beaten path more often and attempts off-road riding again.

In 2014, when she was doing the Borneo season, Tomboy Tarts was able to speak to her about her experiences while filming for that gruelling journey in Borneo. Scroll down for the interview below:

Tomboy Tarts:  Would you consider yourself to be a tomboy?

Jaime Dempsey: I definitely have a tomboy side! I love adventure and crave challenge, especially if it’s something that is generally not thought of for girls. I guess I just like proving people wrong when it comes to these stereotypes.

TT: What was your first ever trip on a bike? How was the riding experience like?

JD: My first road trip was across the US from Philadelphia to Los Angeles, a journey about 4,800 km long. I was moving from the East coast to the West coast and wanted to explore the in-between on my way. I rode about 500km a day and took a southern route through Nashville, St. Louis, Dallas, Albuquerque, the Grand Canyon, and Las Vegas. The journey was incredible, but of course it didn’t go 100% smoothly. The bike’s tire was showing bare thread in the middle of nowhere during the New Mexico leg. It took 2 days to find a tire and find someone to put it one, but it’s all a part of the adventure! I’d love to do it again and take a northern route back to the East Coast one day.

TT: What’s your dream bike?

JD: I have so many dream bikes! When I daydream about motorcycles, it usually involves a garage full of different kinds. I love Harley Davidson® for their smooth rides during long distance. I love Triumphs for their classic styling, and I love the speed of Ducati. But my dream would be to have someone custom build a bike just for me and include me in the design and building process so I can learn and take part in its creation. I envision it having an old school look, with a fast engine!

TT: What are the differences between riding in L.A and Asia?

JD: The very first thing is riding on the opposite side of the road! Also, there is a lot more motorbike traffic in Asia than where I live. I think if more people ride motorbikes in LA there would be a lot less standstill traffic! I noticed a lot more overtaking in Asia, and I had to be much more aware of traffic coming in all directions. The roads in Borneo were a bit rougher than I am used to as well. LA is covered in paved freeways whereas Borneo is much more wild with gravel roads leading into mysterious jungles.

TT: What are the crazy things you’ve done on the show so far on Ride N Seek Borneo?  We heard that you tried ‘ikan buntal’ – a local poisonous fish in East Malaysia. Was that a dangerous experience? 

JD: Riding 29 km on a chunky gravel road with no prior off-road experience into a remote jungle was pretty crazy to me! You will see just how physically challenging it was when you watch the episode. I held a very poisonous snake at Mabul Island which was terrifying yet exhilarating. I had a surprise bloodletting session when I went for a massage in Miri, Sepilok. I helped take care of baby Orang Utans who were so precious that I will never forget them, and yes, I ate the poisonous puffer fish! I was a little bit nervous eating it since watching the women prepared it with such speed. But I trusted that if they thought if it was safe enough for them to eat, hopefully, it would be the same for me. The conclusion – it was deliciously tender! I loved it!

TT: Do people recognize you from the show? Were there any eyebrows being raised from the conservative folk of Brunei when they saw you on the bike with all your tattoos? 

JD: Yes! I was surprised to find people approaching me at all locations for photos or autographs. It was so nice to hear from people first hand that they enjoy watching the show, and it helped in overcoming the challenges of shooting Season 2 knowing that people would be looking forward to seeing it. Everywhere I went, the locals were very welcoming and even admiring of my tattoos. I was able to relate and trade stories about tattoos with the Iban people in Sarawak that really made me feel at home there. I saw many tattoos in Sabah as well. To show my respect for their culture I covered up in Brunei, but I showed them off to Independent MC – a biker gang that I rode with and an airbrushing master who admired the artistic quality of my work.

TT: Will we get to see you get a tattoo on the show to remember your adventures here in Borneo? 

JD: I wanted to get a tattoo to remember my trip while I was hanging out with the Iban. But it was Hari Gawaii (Gawaii Day) and many of them had participated in the tradition of drinking ‘tuak’ (a local toddy) and I wanted to be sure that whoever marked my skin for life was of a clear mind. Haha! Maybe I will have the opportunity in the upcoming seasons. As for what it would look like, I’m definitely open to suggestions, of course!

TT:  What are some of your travel essentials when you’re on the road?

JD: I travel light. When I go for a ride all I need is some chapstick, my shades, and a camera to capture all the places I visit and share them with my friends and family.

TT: What do you want your audience to take away from watching Ride n Seek Borneo? 

JD: I hope to inspire the viewers to get out, try new experiences, meet new people and have fun! Even if it’s not by motorbike! Often you will find that there is much to explore in your own backyard. I was surprised to hear from people I met along the way that they had never heard of Maliau Basin, or seen the orang-utan in Sepilok. I made so many great memories on this journey and I would have never had them if I had not broken my normal routine and gotten out of my comfort zone to explore a place that is so foreign to me.

TT: Any advice for riders (both novice and experienced) who want to ride in Borneo and East Malaysia?

JD: I would advise riders to map their trips out on paper since there are many beautiful places outside of cellular range. Don’t push yourself too hard and try to cover too much ground in a day- stop and smell the roses! For safety I would say, don’t plan to ride at night, make yourself aware of any local traffic laws, and always wear your safety gear! If you are planning on doing any off-roading, it might be a good idea to either take a course before you leave or take one at your destination- I learnt the hard way as the viewers will see! There are a few organizations that plan trips for groups of all experience levels that you can join such as Big Loud Rides or, for off-roading, Borneo Biking Adventures. Following a guide will help to remove some worry about anything going wrong, or getting lost, and allow riders to focus on having fun!

TT: Now that you’re done and dusted with filming Season 2 of the show, where will you be heading off to next?

JD: I will be roaming around California for a while. There is a big bike ride out to the desert in October for girl bikers called Babes in Joshua Tree by a group called Babe Ride Out where over 200 girls will ride and camp for 2 days. I’m really excited for it! In the meantime I will be crossing my fingers that Ride N’ Seek Season 3 will happen and take me to Indonesia, the Philippines, Thailand or somewhere else exotic!

TT: Can we hitch a ride on your next biking adventure? 

JD: If you want to ride with me, you have to ride your own bike! I’ll even teach you 🙂


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Founder and Editor-in-chief at Effort-Lez. Writer, comedian and career lesbian. Interests include, but are not limited to: Kanye West's Fade video, drinking wine & making out (while watching Kanye West's Fade video), cerebral hoarding, three point stands and laughing myself into quadriplegia.

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