Confessions of a two-timer: Double Trouble

Double the fun and double the trouble!

Call it the 7-year itch or just plain “gatalness,” two-timers have a lot to contend with in their daily lives. It is not a walk in the park and neither do they have peace of mind as they are often torn between two lovers.

In this week’s column of confessions, we speak to a Singaporean man who has been married for over 23years and has been having a mistress on the side in the last five years, and a child out of wedlock. Juggling the two families has been a challenge, it obviously has taken a toll on his finances and time.

James, not his real name, turned to his mistress for solace when he hit a rocky patch in his marriage six years ago. “First, it was purely carnal,” he said. Soon the clandestine relationship turned to a deeper meaningful partnership between the two.

James, who is turning 52 this year, says that spending time with his young son from his mistress makes him forget all his worries and woes. “You know, seeing my little boy and playing with him, makes this whole ordeal worth it,” James said.

His first wife does not know about his other family and he goes through a fair bit of trouble each day to cover his tracks well. The situation at the home front has also gotten better and hence James has decided to stay on in his first marriage.

He speaks fondly of his mistress too – about how she is raising his son and how docile she is. Often contrasting her with his wife.

But when it comes to PMS-es, he has twice the trouble compared to all the singletons out there. The mistress gets all stroppy and uncooperative and threatens him that she’ll go to his wife with the truth. “I just give her (his mistress) some time by herself to think and reflect, after all, she knew what she was signing up for,” he said.

Obviously, such indulgences are not for the average Joe. He goes through quite a bit each month to maintain two families – paying the bills for two housewives and three kids, two of which are grown up.

Having a third child so late means that he needs to be gainfully employed for another two decades to keep up with the expenses. “My mistress is fifteen years younger and hopefully she can pick up some slack as I grow older,” he said.

The tricky bit about all these, is dealing with the gossip in social media. I need to keep my private life away from social media glare, he said. So that my wife and kids from my first marriage don’t find out.

“I’m mentally prepared for the final showdown. When my wife finds out and kicks me out of my marriage… But I don’t know how to face my kids. That’s gonna be an awkward moment for me,” he said.

James is also worried about how he is going to split his estate after his time. He knows that he needs to put it down on his will and he knows that it is not going to be so easy going for his children when it comes to partitioning his wealth.

Quoting an old English adage, James said, “If there is a marriage without love, there is a love without marriage. We only live once!”


  1. No matter how tough life gets.. you should not get involve with another.. heart ache will definitely follow if you do. Always be faithful to your wife.

  2. monogamy is odd, why is polygamy illegal?
    this will increase our fertility rates. man needs more than one wife. by allowing polygamy, the 2nd woman can have the legal status of a 2nd wife. and her children will have the proper legal status.

    the law on one-man, one woman must be changed.

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