I first met Jessica* four years ago at an interview for a part-time job at an American multinational firm. I was looking for a temp gig to fund a trip to Europe before starting university. Jessica, my interviewer, was nine years older than I was (20 then), but I was instantly drawn to her – she was petite, with a hot body and an attractive face. The interview proceeded professionally and I left, thinking nothing of it. Later that week, Jessica called to say I’d got the job.
We spoke briefly about the position but somehow veered off-topic, chatting casually about our weekend plans. On the spur of the moment, I even asked her to join me at a club with my friends but she laughed and said no. Later that night, after a few drinks, I ended up drunk dialing her. I can’t remember the details, but she humoured me, chatting with me about my night. Surprisingly, she seemed relaxed about the whole thing. More surprisingly, I didn’t get fired before I had even started my job.
When I did start work, we continued our casual relationship via SMS, even though she was my boss. We bonded easily over common interests like music and outdoor activities, and quickly built a tight friendship.
We would send flirty text messages to each other throughout the day at work and late into the night. This lasted for about two weeks before I plucked up the courage to ask her out for drinks. We ended up kissing that night. Despite the age gap, there was definite sexual tension and I was really attracted to her. Plus, she was fantastic company – outgoing, funny and spontaneous.
After that, we’d secretly meet at lunch or after work at least four times a week. She would pick me up in her car, but always at a distance from the office – she was very careful because she was holding a senior position at the company. I remember her flipping out when I added her on Facebook, terrified that our colleagues would notice.
We eventually progressed to having sex at her downtown apartment (she rented her own place with a housemate). Sex with her was hot and steamy, and soon I was spending nights over.
The perfect relationship
Despite all the time we spent together, we never had The Talk. Our relationship had no real definition – I knew she had broken up with her long-term boyfriend right before we’d met. For a guy, it was the perfect arrangement – she was hot, the sex was great and there was no commitment.
Plus, there were some seriously unexpected perks.
Even though I constantly offered to pay when we went out, she would always pick up the tab, even if we were at a high-end restaurant. She would always send me home after a date even though we lived on opposite ends of the island. She even gave me a smartphone worth over $800 to replace my ratty old model when she picked up a new one for herself. She had no qualms about doing things usually expected of the man in a relationship – paying the bills, driving us around and constantly having me over at her house.
Three months into the relationship, things got even more serious. This was in the last few weeks before I left for Europe. We would do “couple” things – cancel on our friends to hang out, or she’d skip visiting her parents on weekends so we could meet. Yet, on some level, both of us knew the end was near. I was going away and the age difference meant that we were never going to be a serious item. I think the whole situation worked only on the premise of a definite cut-off point.
We eventually decided that things needed to end and met up to awkwardly say our goodbyes. But the night before my flight, Jessica asked to see me. When I met her, she passed me an envelope, asking me to open it only when she had left. She told me to have fun in Europe.
In the envelope was a huge wad of cash – $800, to be exact. I called her up, asking what the money was for. She said she knew she wasn’t going to see me again, but just wanted me to be safe in Europe. She told me to keep the money in case of an emergency, as I was travelling on a shoestring budget. Although I was angry that she’d given me such an unnecessary and extravagant present, I was touched by her concern.
I never used the money and I transferred it back to her after my trip. I’ve never seen her again. Looking back, she was an amazing person. Besides being successful and confident, she was also warm, kind and sincere. It was interesting to be in a relationship where the woman looked after you for a change – a role that’s come to be expected of guys. And even though things were mostly physical, I learnt a lot from her self-assured way of life.
My cougar magnet days
My relationship with Jessica sparked a change in me. Suddenly, the petty concerns and ridiculous obsessions of women in their early 20s just didn’t cut it anymore. Even though I’d had two relationships with girls my age, their insecurities and constant need for reassurance over trivial matters were exhausting compared to the confidence of older women.
Being with older women quickly became something I enjoyed. I knew that the relationships had no emotional foundation or future but that didn’t deter me. My cougar magnet days had begun.
After Jessica, I’ve been with nine other older women over the last four years. There was the divorced friend of a former tutor, two doctors I met in the US while on a university exchange programme, a corporate high-flier – these are just a few. All of them were more than eight years older than me.
My wildest encounter was with the doctors in the US. I met two of them on a night out and ended up sleeping with both the same night. I didn’t even make the first move – they propositioned me 20 minutes after we met.
Among all these women, Jessica was the exception – we were a couple in everything but name. With the other women, it was mostly physical. Some were one-night stands, and almost all the women made the first move.
We do elicit strange stares when we’re out, but most of the time, these women prefer to keep things on the down-low – so many hours are spent in bedrooms, back seats and quiet, nondescript bars.
I’ve told some close friends about the cougars, but they’ve only met one of them – a corporate high-flier named Rebecca*, who showed up at a club where I was partying with friends and bought everyone a round of drinks. My friends, who used to taunt me about my secret relationships, were left with their mouths agape.
The women I’ve been with are usually successful, confident and in control of their career and finances. But they often have had no time for love, and some had recently ended relationships when we met. They wanted someone who’d listen to them. And they also wanted no-questions-asked sex.
I’m not sure what it is about me that pulls them. Perhaps it’s because I’m not shy about letting these women know that I’m checking them out even if they’re older. I think women can tell when you’re not intimidated by their success. The simplest explanation I can offer: these women seek a non-judgmental guy willing to show them a good time without any strings attached.
I just happen to be that guy.
Over the years, though, I’ve laid out some ground rules. No boyfriend or a husband in the mix, nor a girlfriend on my end. More importantly, I always make it clear that I’m not seeking a relationship and most of them have been more than happy with this arrangement.
No, I’m not a hooker
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.
*Names have been changed
This story was originally published in the February 2013 issue of Her World.