My latest squeeze, Rebecca, is a successful healthcare executive in her early 30s. I've never asked her age but I think she must be about eight years older. We met a year ago and she is a prime example of the type of confident cougar that I easily reel in. I first saw her at a fancy hotel bar which has the reputation of being flush with social escorts. I noticed her immediately, no thanks to her sexy red dress.

When she came up to my table and started chatting, I immediately put my guard up - more so when she asked me to dance. I openly hesitated, worried there might be a financial transaction required at the end. But she looked straight into my eyes and whispered into my ear, "I know what you're thinking and no, I'm not a hooker."

Smitten by her brazenness, I spent the rest of the night trying to get her to dance with me. We eventually exchanged numbers. Since that night, Rebecca and I have been what you might call "friends with benefits". There's no talk about children, cohabitation or commitment - in fact, she's incredibly emotionally guarded.

I listen when she needs to let off steam about work and I'm there if she needs unwinding of a different sort. She's good-looking, rich and successful, and I don't understand why she's with me. But I'm not complaining. Even though we don't have much in common, I love her spontaneity - one Friday night, I got a text from her that read, "Got a room at Marina Bay Sands. Come over now."

When I got there, she had a bottle of champagne waiting. She said she just felt like having a staycation. Yes, we definitely stayed in that night.

The cougar hangover

I recently found out that Rebecca spilled to a girlfriend about our "situation". She sent me a text a few weeks ago that was uncharacteristically needy - asking why I never asked about her day. Though she texted me soon after, telling me to ignore the message and that she had been drunk, things have been slightly weird since. Honestly, I'm not sure how things will turn out.

Right now, I wouldn't consider a long-term commitment with a much older woman. My family would never approve and it'd be difficult to handle all the judgment that comes along with it. I might feel differently when I'm much older, when an age gap of six or seven years won't seem as drastic as it does now. But since marriage is not what I'm after right now, I'm happy with my "unique relationships".

Whenever I'm at a bar, I can't help but notice women who are obviously older. I'm not sure if my preference for cougars is veering into problematic behaviour, but I have no regrets. I've come to realise that they're just normal women who differ from their peers only in their longing for adventure, openness to dating a younger man and willingness to identify themselves - at least for a night - as cougars. And I can't help but respect that.

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