Saying that he felt 'lost' after the relationship ended, he spent a lot of time in pubs and bars, where he would often pick up the bills for his drinking sessions and pay with his credit card.
His other pastime was gambling, which accounted for the bulk of his debt.
He lost $50,000 on online casinos, football betting and 4-D over a three-year period.
James also could not reclaim the $15,000 that he gave his ex-girlfriend to help with her study loan in 2005.
'I lost all interest in daily life. I didn't want to think about my future. I just wanted something to divert my attention,' he recalled.
All this while, the financial analyst remained one of the key breadwinners in his family of six.
A polytechnic graduate, he pays for his mother's post-cancer treatment and has to support two other siblings as well.
When money got tight, he used his unsecured credit facilities to get some quick cash to fund their living expenses and health-care costs - without realising the high cost.
By the time he became aware early this year, he had accumulated $84,000 worth of debt with 10 creditors.
They were breathing down his neck and his mobile phone was constantly ringing off the hook in the office.
His work suffered and he was constantly reprimanded by his supervisors.
Even his friends slowly left him, especially when they found out about his debts.
By the time lawyers' letters were served - he was defaulting on his card payments - he knew he needed help.
He went to Credit Counselling Singapore which worked out a repayment structure with the creditors.
Now, more than half of his $3,300 take-home pay is used to clear his debts.
He has stopped clubbing and gambling.
He feels that what happened to him 'can happen to anyone else, especially those who lack discipline and love from family and friends'.
He said: 'If you want to spend money, use your spare cash. Don't spend money that you don't have.'
This article was first published in The Straits Times on 22 June 2008.