Single this cuffing season? Dating experts share advice on finding a significant other

The dating world can be discouraging, but if you don't play, you can't win. Here are tips to keep in mind when navigating cuffing season.

Colder temperatures symbolize more than the fall’s grand return. For single people worldwide, the seasonal changes mark the beginning of a time dedicated to creating meaningful connections: cuffing season. 

Cuffing season, which closely aligns with basketball season, ideally has seven parallel phases: scouting, drafting, tryouts, preseason, cuffing season, playoffs, and the championship — or a relationship. The schedule is designed to progress an individual through the stages of dating, allowing them to narrow down potential mates until there is only one person. If one wisely used the summer through September for drafting and scouting, October naturally falls during the tryouts section of the season, which means it is prime time to get to know people, go on first dates, and set a solid foundation for any future relationship. 

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The dating world is multilayered; even for the seasoned pro, navigating the how-tos and what-ifs can be confusing. Before entering the dating space, singles and couples therapist Quinelle Hickman recommends people reflect and open themselves up to dating. Reflection requires individuals to identify what they are looking for — and what they are willing to give — in any relationship.

“Reflection looks like sitting down and asking yourself, what [you’re] looking for [and] what [you’re] willing to contribute to the dating experience?” Hickman said. “You have to be willing to understand that there [are] some things in a relationship or a person that you’re going to love, and there’s going to be some things that you don’t like. It’s not going to be sunshine and roses every day, but are you willing to accept the person for who they are without trying to change them?”

The reflection period looks different depending on gender identity. For instance, Cassandra Menard, a relationship and life coach for men, advises her clients to define what being “a good man” means to them and identify what is preventing them from becoming that ideal and living in that space every day. 

Anwar White, a dating coach for Black and brown women, suggests his clients acknowledge their inner wounds, learn how to be vulnerable, set boundaries, and work to recalibrate their feminine and masculine energies. Like Menard, he advises the women he works with to continuously work on becoming the best versions of themselves while dating. 

“Dating is not about finding your husband because when you focus on that, you center the institution of marriage, and you center the guy,” he said. “Dating is about how you level up and learn about yourself. I always tell my clients, my job is to help you become the woman that is ready for the best relationship with your life.”

Hickman also recommends singles acknowledge there are areas they can improve and establish clear dating goals. Clear dating goals will help individuals set boundaries and allow them to date intentionally. In our modern world, there are so many ways to meet people, and singles should be open to different avenues. 

White said he thinks about love in abundance and tells his clients they need to date both “online and offline.” While online dating has its positives and negatives, many singles have found success on the apps. One out of every 10 partnered adults met their significant others using a dating site, according to a Pew Research Center report

Remember, apps like Bumble, Hinge, and Coffee Meets Bagel are seasonal. White recommends singles try all of them for about eight weeks, alternating between apps, to get the best results. He also suggests singles switch their profile picture every other month to refresh the algorithm. A profile picture change will prompt the algorithm to register you as a new person — and potentially present a different assortment of people. 

Outside of dating apps, both White and Menard agree singles should meet people in curated spaces. Exclusive places, like conferences, airport lounges, and upscale hotel bars, provide the perfect settings to meet people. Other spaces, such as a gym or special activity that coincides with your personal interests and reflects your character, will help singles attract people with similar interests. 

“As [a single man is] becoming the good man that he wants to become, he surrounds himself and stays in places and spaces that reflect his character, reflects what he loves to do, reflects the character of the man that he sees himself [as],” Menard explained. “[He’s going to be] able to find somebody who naturally matches his vibe.”

Most importantly, singles ready to mingle should show up as their most authentic selves. Menard advises singles to ensure their verbal desires match their actions, be consistent, and be genuine. For men especially, she recommends establishing a role that they can maintain. 

“Don’t impress [the date] with what’s large,” she said. “Impress [them] with being consistent and showing up with what [you have] to offer.”

Remember — it is normal to get discouraged when navigating the dating world. White offered the reminder that most new relationships don’t make it to a third date. Based on statistics, singles will have to have a lot of conversations and false starts before finding their person. It is important to heal your wounds and continue putting yourself out there.

“It’s okay to be disappointed,” Hickman said. “However, … I always like to say [that] it’s like a lottery. You have to play to win.”

Kayla Grant

Kayla Grant is a multimedia journalist with bylines in Business Insider, Shondaland, Oz Magazine, Prism, Rolling Out and more. She writes about culture, books and entertainment news. Follow her on Twitter: @TheKaylaGrant  

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