Kendall Jennerand exBen Simmonsspent the last minutes of the decade together on Tuesday night.During aNew Year’s Eveouting in downtown Philadelphia — where Simmons, 23, plays for the local76ersNBAteam — Jenner, 24, walked alongside her ex and a group of friends to a private party at the rooftop bar Attico, according toTMZ.The sighting comes months after a source told PEOPLE that the on-off couple was “on a break” in May.“The relationship ran its course,” the insider said at the time. “She’s spending time with her friends and back to being in fun mode.”Since their split, Jenner and Simmons have seemingly maintained a friendly relationship and have continued to interact with each other.In August, both Jenner and the basketball player attended abirthday party, along with Jenner’s sisterKourtney Kardashianand her own ex,Younes Bendima, with whom sherekindled a romancelast month.More recently, Jenner was spottedcheering onSimmons at one of his games in Philly in December, nearly seven months after calling off their relationship.Kendall Jenner; Ben Simmons.Taylor Hill/WireImage; Joe Scarnici/GettyJenner confirmed that she had been dating Simmons during an appearance onThe Ellen DeGeneres Showin February.“So obviously you’re dating this guy who’s on the 76ers. How long have you been dating him?” hostEllen DeGeneresasked, before she replied with a huge smile on her face, “For a bit now.”That same month, Simmons and Jenner stepped out for an earlyValentine’s Day datein New York City. Jenner later opened up toVogue Australiaabout their relationship, as well as thepossibility of marriage.“Maybe. Definitely not now, but maybe one day,” Jenner told the magazine. “I got a glimpse of how my sisters dealt with [the attention] and it’s cool to learn from that.”Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest storiesJames Devaney/GC ImagesTheKeeping Up with the Kardashiansstar also revealed why she chose to keep her relationship with Simmons private.“For me, a lot of things are very special and very sacred, like my friends and relationships, and I personally think that bringing things into the public makes everything so much messier,” she said at the time.“I’m very young, and right now I feel like relationships aren’t always super-certain and I don’t want to bring too much attention to something if you don’t really know long term [what it’s going to be],” she toldVogue.She added: “A relationship is only meant to be between two people, and the second you make it the world’s business is when it starts messing with the two people mentally. Like once everyone is let in, you’re letting all these opinions into your relationships, and I don’t think that’s fair.”At the time of the interview, Jenner appeared to be very much committed to Simmons. She FaceTimed the basketball star before sitting down withVogueand even streamed his game while sitting in the hair and makeup chair, according to the publication.

Kendall Jennerand exBen Simmonsspent the last minutes of the decade together on Tuesday night.

During aNew Year’s Eveouting in downtown Philadelphia — where Simmons, 23, plays for the local76ersNBAteam — Jenner, 24, walked alongside her ex and a group of friends to a private party at the rooftop bar Attico, according toTMZ.

The sighting comes months after a source told PEOPLE that the on-off couple was “on a break” in May.

“The relationship ran its course,” the insider said at the time. “She’s spending time with her friends and back to being in fun mode.”

Since their split, Jenner and Simmons have seemingly maintained a friendly relationship and have continued to interact with each other.

In August, both Jenner and the basketball player attended abirthday party, along with Jenner’s sisterKourtney Kardashianand her own ex,Younes Bendima, with whom sherekindled a romancelast month.

More recently, Jenner was spottedcheering onSimmons at one of his games in Philly in December, nearly seven months after calling off their relationship.

Kendall Jenner; Ben Simmons.Taylor Hill/WireImage; Joe Scarnici/Getty

Kendall Jenner and Ben Simmons

Jenner confirmed that she had been dating Simmons during an appearance onThe Ellen DeGeneres Showin February.

“So obviously you’re dating this guy who’s on the 76ers. How long have you been dating him?” hostEllen DeGeneresasked, before she replied with a huge smile on her face, “For a bit now.”

That same month, Simmons and Jenner stepped out for an earlyValentine’s Day datein New York City. Jenner later opened up toVogue Australiaabout their relationship, as well as thepossibility of marriage.

“Maybe. Definitely not now, but maybe one day,” Jenner told the magazine. “I got a glimpse of how my sisters dealt with [the attention] and it’s cool to learn from that.”

Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories

James Devaney/GC Images

Celebrity Sightings in New York City - February 14, 2019

TheKeeping Up with the Kardashiansstar also revealed why she chose to keep her relationship with Simmons private.

“For me, a lot of things are very special and very sacred, like my friends and relationships, and I personally think that bringing things into the public makes everything so much messier,” she said at the time.

“I’m very young, and right now I feel like relationships aren’t always super-certain and I don’t want to bring too much attention to something if you don’t really know long term [what it’s going to be],” she toldVogue.

She added: “A relationship is only meant to be between two people, and the second you make it the world’s business is when it starts messing with the two people mentally. Like once everyone is let in, you’re letting all these opinions into your relationships, and I don’t think that’s fair.”

At the time of the interview, Jenner appeared to be very much committed to Simmons. She FaceTimed the basketball star before sitting down withVogueand even streamed his game while sitting in the hair and makeup chair, according to the publication.

source: people.com