Dating after divorce: Is it ok to just approach someone on the street if I feel interested?

SINGAPORE: It can be challenging to navigate through life after a major change, such as a divorce. A newly divorced person may, understandably, feel at a loss with what to do now that they’re no longer coupled, when they want to start wading into the dating pool again.

This appeared to be an issue for a woman who will be turning 36 in a few months, is in the process of getting divorced, and is thinking ahead about the best way to find a partner again when the time comes.

“If all goes well, I should be officially single within this year,” she wrote, expressing some trepidation, since she hasn’t “been single or in the dating scene for ages.”

She went on to explain that she has no children, works from home, and doesn’t really go out all that often, and acknowledged that she has limited opportunities to meet new people, unless she goes out of her “comfort zone and tries something new,” such as going to the gym.

While she’s open to trying getting on dating apps, she did not seem to be keen on the idea, since she finds matching, chatting, and arranging dates to be “quite time consuming… not very time efficient and low ROI in my view haha.”

However, her real question is this: “I was wondering if it’s weird or too bold to just approach guys at cafe or on the street if I feel interested. Never done that before and (I’m) afraid I might freak them out.”

She added that she “would love to hear thoughts or experiences from people who started dating again after divorce.”

The top comment came from a Reddit user who appears to believe that if a person is attractive, they might go ahead and approach a stranger to ask them out. If otherwise, they joked, they should “prepare to get a police report.”

A person who went through the same experience as the post author had this advice to give. “Dating is tiring, but it’s not really a problem or the apps. It does take time and effort to get to know people, and when you’re at this age, things are more complicated since you consider things like lifestyle, finances, shared goals, etc., and not just ‘vibes’ unlike in school.

You can definitely approach someone you fancy on the streets, just that it may not necessarily be easier than the apps.”

Others were more discouraging of this method, suggesting that the post author try sports or sites such as meetup.sg instead.

Some, however, gave the post author the thumbs up.

“Walk up to him if u are interested. Worst u can get is, ‘I am attached,’ or, ‘Is this for Tiktok?’ Trust me, even after 15 years, a guy will remember that exact date, place, his outfit and the outfit of the girl who walked up to him and shared the slightest compliment,” another wrote.

A male Reddit user wrote, “Personally, I would actually like it a lot if someone approached me in real life, but I suspect most Singaporean men would be a little freaked out.”

“Approach guys not weird lah. It’s just very rare here. Most guys will freeze for 5 seconds, brain lag, then go home and tell their friends for the next 10 years. Freak out maybe, but in a good way.

Dating apps are a necessary evil. Treat it like Shopee browsing, not full-time job. Swipe a bit, chat a bit, if boring then close the app.

Also, 36 in SG is not ‘expired.’ It’s ‘emotionally stable, knows what she wants, don’t play games.’

Honestly, that’s premium tier already,” another commenter added. /TISG

Read also: ‘He only brushes his teeth once a week’ — Husband’s poor hygiene habits push woman to consider divorce