🇿🇦 South Africa: A Wild, Life-Changing Trip

The trip begins in chaos

• Comedian Big Jay Oakerson traveled to Cape Town for a comedy festival while dealing with the fallout of being caught cheating on his partner, Carla.
• He left for South Africa emotionally overwhelmed, then endured a long flight in a middle seat—with sore, bleeding elbows after getting impulsive star tattoos the night before.
• While away, he discovered that the woman he’d been seeing had posted a nude photo of him on Craigslist. Friends alerted him and helped get the ad removed; Jay later said he felt he deserved consequences, but not for the image to spread widely.

Cape Town and the comedy festival

• Jay stayed at the Table Bay Hotel, a luxurious waterfront hotel with an elaborate breakfast buffet and views of Table Mountain.
• He was struck by the landscape, the city, and the mix of cultures—very different from the Africa he had imagined.
• The favorable exchange rate made it possible to have memorable nights out and even buy drinks for an entire bar for relatively little.
• The festival brought comics together as a team. Jay found unexpected support from Todd Lynn, who regularly encouraged him to get out of his room and explore while he was feeling low.
• One awkward moment came when Todd explained his anger as being a Black man living in America. Other comics pointed out that South Africans had only recently emerged from apartheid, making the remark especially uncomfortable in context.

Exploring South Africa

Jay and Carla spent the final week of the trip together and visited several places:

• Townships: They took a drive through local townships and visited markets, where they watched craftspeople at work and bargained for souvenirs.
• Table Mountain: Jay admired it from his hotel room but didn’t take the cable car to the top—a decision he still regrets. He later learned the rotating cable-car floor gives everyone a view, and that there’s food and drink at the summit.
• Seal Island and whale watching: They went out on the water, but most passengers became seasick. They saw penguins, but no whales, and didn’t witness sharks breaching for seals.
• Cape Point: They visited the area where the Atlantic and Indian Oceans meet.
• They also enjoyed a striking seafood dinner and bought souvenirs—including ivory chess sets that Jay later recognized were likely illegal.

Reconciliation and what the trip meant

• Jay’s grandmother offered to fly Carla to South Africa so the couple could talk away from home and other people’s opinions.
• Their conversations were difficult. They briefly discussed trying a more open relationship, but Jay realized Carla wasn’t genuinely comfortable with the idea.
• They returned home to a rocky relationship, but ultimately reconciled and stayed together for about 11 more years. Jay felt that the time they gained together mattered for their daughter, Isabella.
• The trip was both a painful escape from the consequences of his actions and an opportunity to reconnect with Carla and experience a place far beyond his expectations.

Key takeaway ✈️

This is more of a personal travel story than a destination guide: the focus is on how the journey unfolded, the people Jay met, and the experiences that stayed with him. His clearest travel regret is simple: if you visit Cape Town, don’t skip the Table Mountain cable car.