In March 2001, Cary Tan, founder of Club Herstory, organised a walk by 31 gays and lesbians around the Zouk disco complex in what they believed to be Singapore's first pride parade. However, a similar claim was earlier made by Alex Au of PLU in December 1993 for an impromptu walk by gay men in fancy dress from Boon Tat Street to Lau Pa Sat.
In April 2001, the Gender Identity Clinic at the National University Hospital, which was an offshoot of the original subsection of the Department of Obstetrics and Gynaecology at Kandang Kerbau Hospital and which helped to build Singapore's reputation as a top destination for sex change operations for the past 30 thirty years, the last hospital in Singapore for such procedures, closed without any fanfare. The official explanation was that the gynaecologist in charge had left for private practice, and without him, the clinic did not have the skills to perform SRS. However, as early as 1987, the Ministry of Health had been directing hospitals to stop doing such operations on foreigners. It also discouraged them for Singaporeans, saying 'the increased danger of AIDS with such patients poses unnecessary risk to hospital staff'. However, some believe that the increasing number of Christian doctors filling the administrative ranks of Singapore hospitals over the past decades had a part to play in its shutting down as cross-dressing and sex reassignment are proscribed in the Bible.
This dismayed transgender people seeking to have their operations performed locally. The online edition of the now-defunct newspaper Project Eyeball carried out a survey in June 2001 asking, "Should sex-change operations be resumed in Singapore?" 39% of respondents said, "Yes, they are people with valid medical needs, like infertile couples" and 35% said, "Why not? It is legal here, as are transsexual marriages". The results showed that Singaporeans were generally quite supportive.
The transgender community's petition was successful, with the clinic discreetly resuming it services in 2003, helmed by Dr. Ilancheran. However, owing to the discrimination against transgender people in Singapore even within some segments of the medical community, the high financial outlay involved and the necessity for psychological clearance, many preferred to have their operations performed sans the hassles in Bangkok, which had by then become the premiere centre for sex-reassignment surgery (SRS).
In May 2001, the Singapore Repertory Theatre produced the play "Shakespeare's R&J", directed by Tony Petito. It was a revisionist version of Romeo and Juliet in which all the roles were reprised by men.
On Sunday, 20 May 2001, the Singapore AIDS Candlelight Memorial 2001 was held at the Youth Park (National Youth Council)along Somerset Road. It was the first time that the event was conducted in both English and Mandarin as many Singaporean people living with HIV/AIDS (PWA) and family members are Chinese-speaking.
In May 2001, rumours circulated that Venom disco, well known for holding gay nights on Sundays since 1998 were allegedly refusing entry to several people who were suspected of organising competing gay parties.
In June 2001, Actions for AIDS (AfA) organised a charity bike ride called 'Riding for Life 2001' which raised S$50,000 for the AIDS Medicines Fund set up in 1999 to help financially-strapped people with AIDS (PWA)s meet their costly drug bills, which could amount to $2,000/- per month. 28 cyclists, including straight celebrity adventurer Khoo Swee Chiow, peddled 900km over 5 days from Kota Baru in the northeast of Malaysia to Singapore.
In June 2001, Time magazine interviewed a Singaporean gay man, Kelvin Wong, and published a photograph of him in its feature on the local gay scene entitled "Boys' night out". Wong was also the first gay man to be featured in a Fridae article.
On 8 August 2001, Fridae organised Singapore's first large-scale LGBT private event at Sentosa's Fantasy Island. 'Nation' was dubbed by the foreign media as Singapore's 'coming out party'. Over 1500 paying gay revellers celebrated both the eve of National Day, as well as their sense of community. Many flew in from Sydney, Malaysia, the US and Hong Kong. The venue was divided into three zones: the Centro Boyz zone where the Miss Divastating drag competition was held, the Womyn's zone where no men were allowed for most of the evening, and the Chill Out area where guests could mingle and booths were set up to sell food, drinks, toys and to distribute flyers. 8 to 10 uniformed Police officers made their obligatory visit at around 11:30 pm to check that everything was all right and left without incident after 15 minutes. The mega-do also raised funds for local safe-sex group Action for AIDS (AfA) who received a portion of ticket sales.
In October 2001, The Necessary Stage staged a play called "Abuse Suxx!!!" which featured a scene in which the 2 male leads kissed each other. It also starred Singapore's iconic cross-dressing comedian, Kumar.
On 1 December 2001, Fridae and Action for AIDS organised Crystal Ball at dbl 0, Singapore's official World AIDS Day party,. It raised S$12,000 for AfA's AIDS prevention and the Medications Assistance programms to alleviate the financial burden of acquiring expensive but otherwise effective medication for needy patients.
On 24 December 2001, Fridae published a profile of openly gay Public Service Commission scholar and geotechnical engineering Masters degree holder Lim Chi-Sharn. Lim, together with his mother, later also provided invaluable insights into the Singapore Armed Force's handling of recruits who declare themselves as homosexual, a process which had hitherto remained largely unknown to the gay community at large,,. This was because the vast majority of gay enlistees did not declare their sexual orientation to the SAF, mainly due to the fear of discrimination during their National Service stint and more importantly in their future careers, especially if they chose to work in the public sector. (See the main article Discrimination against homosexuals in Singapore).