Hindsight is 20/20. We got women in their 40s and 50s to share the advice they’d give their younger selves.

Portrait of Tammy Strobel

Hindsight is 20/20. We got women in their 40s and 50s to share the advice they’d give their younger selves.

My Reading Room
Be present and be you

“I’m not even sure I dated that much in my 20s. Sure, there were some crushes and fyings, but until I corrected my squint – a birth defect which gave my eyes an unfocused look – I’d always been insecure about my appearance. What I’d tell my younger self: You are so much more than your squint. So don’t be self-conscious. Be at ease and completely present with your date.” – Anthea Ong, 48, entrepreneur

Never forget what attracted you to him

“When I was 22, I adored how my boyfriend (later my husband) was a steady force in my life. When my dad passed away, he was always there to help, was gentle with his words and calm as the ocean. But after my career skyrocketed, what had impressed me before suddenly irritated me. As I travelled for business, he questioned my priorities – family or work? His steadiness started to look like inflexibility! But I eventually realised he was right and recalibrated my life. So, never lose sight of the qualities that drew you to your husband in the first place. My man was, and still is, my inner conscience and compass.” – Regina Chua, 50, executive coach and strategic process facilitator

Don’t conform to his idealised version of you

“Not sharing the same interests isn’t a deal-breaker. Actively disliking what your partner loves is. It’s okay to enjoy drinking and a night out with friends. But that guy who thinks it’s ‘unladylike’ and shames you for it? He’s not worth it. You’d just end up sneaking out for a drink and having to come up with lies and excuses. Find someone else who doesn’t sneer at what you love.” – Mandy, 53, financial controller

Forget your checklist

“At a tender age, I decided that I would never, ever marry a Malaysian or someone from a ‘cheena’ school! It was just my ‘preference’. My advice now would be: Look for real qualities and give up silly notions of preferences. Thank God I did. I bonded with my current husband during a church outreach mission to the sick. I remain happily married to him – a Malaysian, and one from a Chinese school at that!” – Mary Ho, 54, homemaker

My Reading Room

“Remember how you used to wear sexy clothes in your 20s because you thought you wouldn’t wear them when you got older? That’s true. But it also meant that you attracted men who were drawn to the way that you dressed! And you know what they say – you reap what you sow.” – Evelyn, 44, business process specialist

Love rewards the brave

“Have courage and don’t be afraid to act on love. I took the plunge and moved overseas after being in a seven-year long-distance relationship… I am still happily married! Love waits for no one. Trust your inner Cupid and don’t be afraid to make an instinctive decision.” – Koh Tze Yin, 50, publisher

Be your own person

“I got married at 19 and gave birth soon after. At the start, I stayed at home and was tempted to continue doing so just to be there for my daughter. If you’re in the same boat, my advice is: Don’t get too comfortable. Don’t hope for your husband to be the sole breadwinner. When my daughter entered her toddler years, I made the right decision to find a job. It kept me active, up to date with trends, and prevented my mind from becoming dull. Always improve yourself so you won’t fall behind as your children grow and your husband advances in his work.” – Grace, 49, finance manager

Financial stability matters

“You don’t have to find a tycoon, but do date someone who is financially stable. It’s okay if he is not earning a lot right now, as long as he has the potential to in the future. If he’s industrious and responsible, he’ll continue to strive and improve his financial position.” – Charlotte, 45, marketing manager

Put yourself out there

“Don’t spend so many hours on overtime work – you’ll never be as dateable as you are in your 20s. Try circular dating (seeing various men at once) and don’t close off your options just because you think you’ve found ‘the one’. Get to know more guys so that you know what works and what doesn’t! Even dating ‘losers’ can teach you a thing or two.” – Ling*, 40, accountant

Think twice about living together

“Moving in together can get messy when your relationship isn’t mature. Don’t rush into sharing your whole life with a man. Assess whether you’re ready to see his ‘unglam’ side – and if he’s ready to see yours. Besides, there’s a certain sweetness in having someone who is happy to walk you home, surprise you with a bouquet of flowers at your doorstep, and chat with you over the phone before bedtime.” – Amanda Chu, 44, homemaker

Watch the family you’re marrying into

“Men I’ve dated used to say, ‘I’m not marrying your mother, I’m m arrying you. Does it matter if your mother and I don’t like each other?’. The answer is: ‘It sure does!’ Happiness is determined by relationships. Poor in-law relationships can break down an otherwise good marriage. I once offered this advice to someone who retorted: ‘It’s already difficult to get a guy. Now you want me to consider his family as well?’ I say it is up to you to elevate your self-worth and afford yourself this luxury of choice.” – Sarah*, 47, teacher


“I remember a guy once said that his mother taught him never to make a girl cry… what she didn’t say was that a girl could make him cry. When you’re young, you are seldom attracted to guys who are sweet and considerate. You want the loud, bold and funny ones… even if they aren’t right for you. Date someone like-minded and who makes you a better person. If that means going for the ‘nice guy’, do so. It is not a ‘boring’ choice.” – Sherry*, 49, lawyer