In 2014, RWM reached a significant milestone when it commemorated five years in the integrated resort industry. The celebrations began on its August 28 anniversary and lasted well over a month. It was during this time that the very first CSR-inspired iteration of LOVE Run With Me was born via an employee-initiated 5K charity fun run held at the McKinley Hill Stadium in Taguig. Limited to RWM executives and staff, the event managed to raise funds in excess of Php 1 million for its chosen beneficiaries, namely the Buddhist Compassion Relief Tzu Chi Foundation and the Pasay Social Welfare Department.
The following year, the same fun run was held at the same venue with the distance being increased to 6K in celebration of RWM's 6th Anniversary. Still limited to RWM employees, LOVE Run With Me was once again able to raise more than Php 1 million for the children of Smokey Mountain, under the care and guidance of the Philippine Christian Foundation (PCF).
By 2016, LOVE Run With Me had gained traction and over 800 runners participated in that year's edition, a 7KM charity fun run in celebration of RWM's 7th year as the country's pioneer integrated resort. This time, RWM invited its partners and special celebrity guests to participate in the race held at the McKinley West Park. A total of Php 1.3 million for the benefit of Caritas Manila, the Lola Grande Foundation for Women and Children, Buddhist Compassion Relief Tzu Chi Foundation, and White Cross Philippines was raised.
Finally, in 2017, LOVE Run With Me was opened to the public with 21K, 10K, and 5K categories. With approximately 5,000 participants, this edition of LOVE Run With Me was unprecedented in that it had six times more runners than the previous year, with almost 2,000 more participants than the 3,000 target. Through the collective efforts of all runners, sponsors, and celebrity leaders, a total of Php 3 million was raised for the various beneficiaries chosen by participating celebrity leaders.
In addition to the run, RWM also supported Mo Twister's Ride With Mo that extended beyond its four walls all the way to the shores of California, USA. At the same time LOVE Run With Me was taking place, Mo biked from San Francisco to Los Angeles-a distance of 917km that took eight days-which he dedicated to RWM for the benefit of the Arthritis Foundation.
In 2018, Run With Me raised Php 3.5 million for the benefit of HERO Foundation, YESPinoy Foundation, ERDA Tech Foundation, Right Start Community Development Inc., EPCALM Adult Leukemia Foundation of the Philippines, and Empowering Brilliant Minds Foundation, with nearly 5,000 registered runners.
In 2019, Run With Me rebranded to Run With Me X in celebration of RWM's 10th anniversary. The event went on to raise a total of Php4 million for five charity institutions: Tahanang Walang Hagdanan, HERO Foundation, EPCALM Adult Leukemia Foundation of the Philippines, ERDA Tech Foundation, Right Start Community Development, along with Save the Children Philippines through Marriott Group of Hotels' Run To Give initiative and the Guam Homeless Coalition through guest celebrity leader, Guam radio personality Ray Gibson. This is RWM's biggest race to date, with over 7,000 registered runners.
Since 2017, Run With Me has been extending support to Filipino athletes by providing a total of 1,941 singlets and finishers' shirts, and over 500 hydration bottles to curb the athletes' personal training and fitness costs. These were distributed nationwide in partnership with Olympian Hidilyn Diaz and Karate Pilipinas National Team Coach and Theater Actor Chino Veguillas.