Diamond's breakout song "Kamwambie" in 2009 was inspired by a heartbreak. The girl in question was Sarah who apparently dumped the heartthrob because he was poor.
In a 2014 interview with Tubonge TZ, Diamond said:
"Huu wimbo nilimtungia Sarah, mpenzi wangu aliyenimwaga kwa sababu sikuwa na masilahi kwake. Nilimweleza kwenye wimbo ni kwa kiasi gani niliumia kwa kuniacha kwake wakati nilikuwa bado nampenda. Nakumbuka siku hiyo yule demu aliniambia, 'sikiza Diamond, mi' kwa sasa siwezi kuwa na mwanaume ambaye hana masilahi kwangu."
"I composed this song for Sarah, my ex-girlfriend who I deeply loved but she dumped me because I was broke back then. In the song, I tell her how much she hurt me by leaving me because I was broke but I still loved her. I remember vividly the day we broke up, she told me 'Listen Diamond, right now I can't continue being with a man who has no means to look after me.'"
YET ANOTHER HIT SONG
Six years later, in 2015, he dropped yet another hit song, "Utanipenda", this time featuring his wife and mother of his two children Zari in the video, asking questions like: would she love him if he was broke?
As if predicting the current scandals that are plaguing his love-life, he sings:
"Na magazeti ya nyumbani kwa kukuza habari si unajuagaa/Utasikia Tafalani eti Mondi kwa Zari amemwagwa/Navyo nilivyo mnyonge tabia ya kuwajibu sinagaa/Kama naiona michambo ya madem wa zamani nilowapitiaga"
"...And you know how newspapers love to create scandals, you will hear there's trouble in paradise, Zari dumps Diamond. But knowing how weak I am, I won't respond to them, just like I scorn my ex-girlfriends whenever they try to seduce me nowadays."
Diamond, who is also known in Tanzanian showbiz circles as Sukari ya Warembo, is indeed a chic magnet.
Lately, the one-time mitumba seller has been trending since he confessed to cheating on Zari with model and video vixen, Hamisa Mobetto, and fathering a child with her.
We take a look at some of the famous women he has dated since 2009:
UPENDO MUSHI 'PENDO'
When he was starting his music career, long before he became famous, Diamond dated bongo flava actress Upendo. They didn't last long however, breaking up after five months.
In an interview later on, Upendo claimed that her relationship with the musician was the worst she has ever encountered in her entire dating life. She even accused him of being bad in bed, according to the interview she did with well-known Tanzanian showbiz blog Mpekuzi in 2014.
"Nimekuwa na uhusiano wa mapenzi na Diamond kwa miezi mitano, lakini hata mara moja hakuwahi kunifikisha kileleni, kwangu mimi namuona kuwa ndiye mwanaume asiyejua mapenzi kabisa miongoni mwa wale niliowahi kukuta nao. Nashangaa kwa nini wanawake wanamgombea."
(I dated Diamond for five months and there is no single time he satisfied me. Among all the men I have ever dated, he is the only one who doesn't know how to make love to woman. I wonder why ladies keeping fighting for him.)
Diamond dated yet another bongo flava actress, Jacqueline Wolper, for several months before they fell out. Even after their split however, the two remained close friends. They worked on several music projects including the 2015 hit song, "Utanipenda", where Wolper was featured in the video.
After Diamond established his music label Wasafi Classic Baby, one of his signed artistes Harmonize started a relationship with Wolper.
Just as with his boss, they relationship didn't last. They broke up in early 2017. Diamond has always denied ever dating Wolper, insisting that they are just long-time friends. Fans will remember that until early this week, he has been denying ever having had a fling with Hamisa Mobeto.
Naseeb is also rumoured to have had a thing with Aunt Ezekiel, one of the most famous bongo movie actresses. Many Tanzanian blogs have, over time, reported that the two never dated but did have several 'one night stands'. Currently, Aunt Ezekiel is in a relationship with one of Diamond's dancers, Moze Iyobo.
The gorgeous Tanzanian model who has been rumoured to be dating Alikiba for the last two years had an affair with Diamond before turning to his nemesis. Diamond started an affair with Jokate while he was still dating Wema Sepetu. The union came to an end when Wema found out that her friend Jokate stabbed her in the back. To date, the two ladies have never seen eye to eye.
After Wema found out Diamond was cheating with her best pal, Jokate, they broke up. Interestingly, it didn't take long before Diamond rebounded with another of Wema's close buddies, Penny Mungilwa. He and the TV presenter made their relationship public, but it was short lived. Once they parted ways, Diamond went back to Wema.
Bongo movie actress, Wema, will go down in history as one of the ladies who withstood the test of time as far as dating this crooner is concerned. Diamond cheated multiple times on Wema not only with Jokate and Penny, but also other women including but not limited to video vixens. Still, she remained loyal. It has been reported that it's for this reason Diamond's mother, Sandra, has always been fond of Wema.
When things seemed to have gotten back on course after mending fences with Wema, it didn't take long before Diamond got back to his usual flirting self. He started having an affair with Zari but when their compromising picture was leaked online, Diamond, the denial king, denied it. He claimed there was nothing between him and the Ugandan socialite, saying that the photo was a shot of one of the music videos they were working on. A few months later, the two went public, declaring that they were now dating.
She is currently the centre of attention after Diamond confirmed that the one month old boy she delivered in August is indeed his. Hamisa conceived while shooting the music video for the hit song, "Salome", where she starred in. During this time Zari was in South Africa attending to her business empire.
Even before the dust on the Hamisa scandal settled, another rumour emerged that Diamond was having an affair with former Big Brother winner, Dillish Mathews. The two were allegedly in Zanzibar last week. However, Diamond addressed the issue by saying that he has never met the Namibian in person. He confirmed that he was in Zanzibar but says he wasn't accompanied by Dillish who also happened to be there.
According to the musician, Dillish was in Zanzibar for a holiday while he was there to perform a show at a friend's wedding.