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.