Entertainment Music From a Whirlwind Engagement to Hailey Baldwin to His Status with Selena Gomez: Inside Justin Bieber's Lady Squad From his Instagram mystery girl to, of course, Selena — and his model fiancée By Grace Gavilanes Updated on July 9, 2018 11:37 AM Share Tweet Pin Email Trending Videos 01 of 09 HAILEY BALDWIN Source Instagram Is this love? Although the pair previously denied being involved in a romantic relationship, it became quite obvious things between the longtime friends were heating up in 2016. Case in point: their PDA-packed New Year's weekend vacation in St. Barts. After some time apart, the pair reconnected. They were spotted spending time and making out in N.Y.C. in June 2018, and in July, PEOPLE confirmed the two got engaged during a trip to the Bahamas. 02 of 09 SELENA GOMEZ Christopher Polk/Getty Ah, Jelena. Their high-profile on-and-off-again relationship continues to fuel endless speculation, thanks to their musical takes on their demise (ahem, "The Heart Wants What It Wants") as well as a flurry of throwback couple photos Bieber posted in December. "I'm never going to stop loving her," he told Access Hollywood of Gomez in November 2016. "I'm never going to stop checking in on her. I don't think if you end a relationship, you should end that, unless it was super toxic and you guys were hurting each other physically or mentally. We always respected each other, and we still respect each other." The couple briefly reunited in 2018 but a source has told PEOPLE Bieber "has no contact" with his famous ex. 03 of 09 SOFIA RICHIE Jun Sato/GC Images It was a whirlwind romance that lasted six weeks and saw the "Company" crooner and his then-girlfriend embarking on a romantic (PDA-filled) trip to Mexico together in August 2016. "We have a special relationship," Richie previously told Billboard. "Justin is very easy to talk to, and that's hard to find with people in Los Angeles." 04 of 09 KENDALL JENNER AKM-GSI The pair has long been close: They spent Coachella weekend together last year, and Bieber helped Jenner celebrate her birthday in November. A day after a source told PEOPLE that Bieber and Jenner's oldest sister Kourtney were "inseparable" and "super touchy-feely," the supermodel and "Sorry" singer were spotted partying together in December. 05 of 09 KOURTNEY KARDASHIAN AKM-GSI "He and Kourtney were nearly inseparable – smoking on the patio together and were super touchy feely," a source tells PEOPLE of their cozy December outing amid a flurry of speculation that Kardashian and Bieber, a longtime family pal, were more than friends. 06 of 09 MYSTERY INSTAGRAM GIRL Justin Bieber/Instagram Buzz heightened about a potential fling with Kardashian after Bieber posted a 'gram of himself and a mystery girl with the caption "Lord knows," possibly referencing the reality star's ex-boyfriend Scott Disick a.k.a. Lord Disick. Paparazzi photos later revealed that the mystery woman in the post was not the Kardashian sister. 07 of 09 CINDY KIMBERLY Justin Bieber/Instagram It was a simple caption that sparked a short-lived (yet successful) search: "Omg who is this!!" Bieber took to his Instagram in December to call out a mystery beauty. With the help of his followers, the Instagram girl in question appeared to be found – and had a relatable response to the ordeal: "I so do not know how to deal with this." 08 of 09 ADRIANA LIMA Getty (2) The Victoria's Secret Angel shut romance speculation during an appearance on Watch What Happens Live in December. "Where did you hear that?! Where?" Lima asked host Andy Cohen. "Anybody below 6-foot-7, you know how I call them? Friends," she continued, ruining any chance of a potential love story (Bieber is 5-foot-9). 09 of 09 JAYDE PIERCE Instagram "People think Justin must be a brat and arrogant, but he's nothing like that," the British model told the Mirror in August. "He's a really tactile guy. He loves cuddles." The two were spotted together in May and vacationed together in Bora Bora back in October – when those nude photos of the singer were published. "I feel like I can't step outside and feel like I can go outside naked," Bieber said of the incident. "Like you should feel comfortable in your own space."