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In the dating world, if you’re into someone, let them know and show your interest. Yet, be ready to accept that the feeling might not always be reciprocated.

Last December, Ismael Pérez had a firsthand taste of why it’s considered the toughest month for matching on dating apps. Their story began around Christmas, followed by the other person’s week-long trip with no phone access. By the time they returned to Chicago, our storyteller was off to Texas for a best friend’s wedding.

Despite three weeks of online chats, their connection lost its spark. They met for a polite, but uneventful date, marking the end of their brief online encounter.

Tired of the draining cycle of chatting for ages before meeting, our Chicago local decided to ditch the dating apps this December. They chose a more traditional route, leading to four first dates through speed-dating.

The adventure began at Tabu in Fulton Market, with a bold entrance and a strong cocktail in hand, aptly named “The Devil Made Me Do It” Feeling attractive and enigmatic, our protagonist caught the attention of a charming individual. The two struck up a conversation, and our Chicagoan, feeling confident, asked to move in closer.

Dressed for a night of speed dating, Ismael Pérez stepped into the Chicago scene with a mix of anticipation and excitement. As he got closer to someone interesting, he thought, “Is this it? Am I really connecting with people naturally?”

In the midst of moving closer, Ismael accidentally spilled half of his cocktail. No big deal, though. He figured it might even make him stand out among the other guys. Interestingly, the guy he was chatting with was also there for speed dating. But let’s get back to him a bit later.

Ismael gathered tips from friends, recent acquaintances, and even the speed-dating event host for those thinking about trying speed dating.

Best Time for Speed Dating?

That Wednesday night, there were five participants, including Ismael. On occasions when he was the odd one out, the host shared insights about group sizes. Smaller groups are more common on weekdays, while weekends attract larger crowds.

For Ismael, the smaller group was a perfect introduction to speed dating. It’s really about what you feel comfortable with. You can start small or jump into the diverse dating pool that Chicago offers.

Key Tip for a Successful Speed Date

Each date lasted six minutes, with a two-minute warning signal. It’s daunting, especially when you’re trying to impress someone. Ismael’s priority was finding out if his date could keep up a conversation. Reflecting on it later, he realized he could have flirted more.

If you sense a strong emotional or physical connection, don’t hesitate to show your interest. Compliments like “I love your smile” or straightforward comments such as “You’re very sexy” can make your intentions clear. It’s important to let them know you’re interested in seeing them again.

Heading into speed dating, Ismael Pérez didn’t have grand expectations. He knew he wasn’t in a high-budget dating show with Chicago’s finest waiting to sweep him off his feet. His advice? Go in without any expectations and keep an open mind about who you’ll meet.

You might bump into someone unexpectedly charming or someone more mature with life experiences to share. Or perhaps someone you wouldn’t usually consider but find intriguing.

Ismael did score one match that night, but, interestingly, it wasn’t with the cute guy he initially hit it off with. Their conversation had veered into a Thanksgiving turkey mishap. As the guy suggested a loose oven door might be the culprit, Ismael realized he was too wrapped up in his story to steer the conversation to more flirtatious territory.

Hoping for a system error or a mistake in the online matching process, Ismael had to face the fact that there was no mutual interest. Time passed, and so did the possibility of a connection with him.

The next day, Ismael took a practical approach: he fixed his oven door to avoid any future undercooked turkey stories. He’s moved past the rejection and suggests the same for anyone in a similar situation. Sometimes, it’s just about taking the experience and learning from it.

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