Relation-tips: Is it ever appropriate to date a close friend’s ex?

Christal: I don’t believe there is ever a situation that warrants dating someone that a friend was in a serious relationship with previously. It’s likely the outside person could have ulterior motives for wanting to date their ex’s friend, even if they aren’t consciously aware of their intent. Getting into a relationship with a friend’s ex can seem exciting, leading to a heightened sense of enjoyment until the reality of the situation sets in.

I think in most cases dating a friend’s ex will result in the original friendship being damaged beyond repair. Often people carry longstanding emotions for the exes even though they are no longer in a relationship with them. This could cause major issues and inevitably often destroy both relationships. When you factor in the likelihood of the relationship not lasting, it doesn’t seem worth the risk. Yes, finding true love is rare, but it’s not so rare that it can’t be found outside your close friend’s ex-lovers.


If you have a question you would like to see featured in “Relation-tips,” email it to [email protected]. You can follow relationship expert Terry Deron at @terryderon and rolling out’s Relationships Editor Christal Jordan at @enchantedpr.

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Dr. Christal Jordan-Jennings
Dr. Christal D. Jordan Jennings is a journalist and professional entertainment publicist with several years of experience in celebrity marketing and branding. Jordan worked in the corporate PR sector before relocating to Atlanta, GA and founding Enchanted Branding and Public Relations in 2008. The company specializes in public relations strategy, media training/consultation, and crisis communication in service of notable celebrity talent such as TLC’s Chilli, Roy Jones Jr.,Kenan Thompson, and more. Further, Jordan serves as a journalist. She serves as editor-in-chief for Lenox & Parker, Sr. Editor with with Rolling Out and Sr. Features writer with Collider, where she specializes in stories that emphasize the importance of empowering women. Jordan earned her Bachelor of Arts degree in Organizational Communications and her Master of Arts in Mass Communications from the University of Oklahoma. Most recently, Jordan started a YouTube channel pulling from her own experiences with celebrity endorsement and strategic relationships. The channel, entitled From Christal with Love XO, boasts over 27k subscribers and works to celebrate love and relationships from a progressive lens. She is also the host of Fox 5 Atlanta’s bi-weekly segment on celebrity relationships. After twenty years of notable stellar contributions in journalism, public relations and literature, Christal received an honorary doctoral degree in Literary Studies from TIUA in June 2024.
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