I Went on a Date with My Brother’s Friend – It Was a Setup

My brother recently arranged for me to go on a date with his friend Stewart, which ended up being a disaster. We found ourselves stuck at a fancy restaurant with an unpaid bill, and as the manager threatened to call the police, I realized the extent of Adam’s plan. I was left wondering how we were going to get out of this mess.

“You need to meet this guy, Jess,” Adam said, his face lit up as if he had just discovered something amazing. He was comfortably settled on my couch, channel surfing.

“Who are you talking about?” I asked, still focused on my laptop.

“Stewart. He works with me. He’s a great guy. Solid job, nice car, the whole package.”

rolled my eyes. “Is this another one of your setups?”

“No, seriously! He’s different. You’ll really like him. And he’s been asking about you.”

I sighed, skeptical due to Adam’s bad track record with setups, but his enthusiasm about Stewart made me curious. “Alright, but if this goes poorly, I’m not going to trust your setups anymore.”

Adam smirked. “Deal. You’ll thank me later, trust me.”

I spent the next few hours preparing carefully, wanting to make a good impression despite my reservations. By the time I was ready, my apartment was a mess from all the makeup and clothes. Despite my anxiety, Adam’s encouragement kept me going.

Stewart arrived in a shiny new sedan. As I got in, I couldn’t help but notice the car’s clean leather smell and the smooth hum of the engine.

“Hi, Jess?” he greeted me with a genuinely warm smile.

“Yes, that’s me. Nice to meet you, Stewart.”

“Likewise. You look great, by the way.”

I blushed, feeling a bit more at ease. “Thanks. So, where are we heading?”

“I thought we could try this new place downtown. It’s fancy, but the food is amazing.”

“Sounds good,” I replied, surprised by the upscale choice.

Sasha Obama’s boyfriend learned something important when their relationship started.

Sasha Obama and Clifton Powell Jr. seem to be getting serious in their relationship. They started dating in 2022 and have kept their romance private and mostly away from the public eye.

In an interview on the “Dear Fathers” podcast, Clifton Powell, the dad of Clifton Powell Jr., talked about his son’s relationship with Sasha Obama, the youngest daughter of Barack and Michelle Obama. He mentioned that they had been dating for a year before their relationship became public, which gave him a chance to teach his son important values.

Clifton Sr. said, “It has helped me talk to my son about how to treat Sasha Obama because we really like the Obamas. I need to make sure my son is responsible, kind, loving, and supportive.” He often reminds his son to be a gentleman and to take care of Sasha. He texts him regularly, saying, “Treat Sasha like you would want someone to treat your daughter.” This advice makes sense, especially since Clifton Jr. is dating someone so well-known.

Is Clifton and Sasha’s romance Obama-approved?

Dating a former first daughter can be tricky, but Clifton Powell Jr. seems to manage it well. It looks like he has the Obamas’ approval. In a 2022 interview with “Good Morning America,” Michelle Obama openly talked about her daughters’ dating lives.

Michelle Obama thinks it’s “wonderful” that Sasha and Malia Obama are exploring different relationships and looking for partners. She said, “I want them to know what they want and who they are in a relationship, and that takes trying out different people.” Barack is “good with it” too. Michelle added, “They’re in their 20s. They went to prom and have lived their lives.” She mentioned that Barack has learned to be a caring dad without being overprotective.

Clifton Powell Jr. also seems to have passed the “sister test.” Malia was seen spending time with him shortly after it became known that he was dating Sasha. The two were spotted walking and talking in a Los Angeles park, appearing relaxed despite the paparazzi nearby.

Is Clifton the one?

Before dating Clifton Powell Jr., Sasha Obama was rumored to be dating Matt Metzler. They sparked dating rumors in 2017 when they were seen kissing at the Lollapalooza Music Festival, but it was unclear if they were officially a couple. After that, Sasha started dating Powell Jr. in 2022, and they have been together ever since.

It looks like Sasha’s parents support her relationship. In a 2022 appearance on “The Ellen DeGeneres Show,” Michelle Obama talked openly about her daughter’s dating life, saying, “Now they are bringing home grown men. Before, it was just pop bands. Now they have boyfriends and real lives.”

As for whether Clifton Powell Jr. is the right match for Sasha Obama, it’s hard to say what the future will bring. However, it’s nice to see that they are enjoying their time together like any other young couple.

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