Jennifer Lopez and Drake Dating? Timeline

After a few months of are-they-or-aren’t-they conspiracy theories, the pair — who first sparked romance rumors back in December after the rapper was spotted (twice!) at the singer’s Las Vegas show — have ended their whirlwind relationship … which an insider close to the rapper revealed “was never very serious” to begin with.

As we mourn the loss of what could have been, we’re taking a look back at Drake and J Lo’s relationship timeline, which started off as a musical collaboration and blossomed into “having fun” up until their demise.

They ‘Really Respect Each Other’: Dec. 22

“They seem to really like and respect each other, but it’s early,” an insider told PEOPLE. “Where it goes, we shall see. Friends of them both are hoping it becomes something, but it’s too early to say more than that.” Further sources revealed the pair was spending time together because of a future song collaboration. “They’re making beautiful music together,” said the source. “They are spending a lot of time together and really enjoying each other, but right now it’s about the music.”

J Lo Is ‘Smitten’ with Drake: Dec. 28

While Lopez and Drake “do work on music together,” the pair also “clearly enjoy each other on another level, too.” A source told PEOPLE: “Jen loves the attention and she seems very happy to be spending time with him. Drake is very charming. He treats Jen with lots of respect. She seems very smitten.”

J Lo & Drake ‘Seem Really Happy’ Together: Dec. 31

“Jennifer and Drake seem really happy,” a source shared, though “friends have no idea where the relationship is going.” The source added that Lopez is over her relationship with on-again, off-again beau Casper Smart, and “that there is no way she is going back to him. She moved on months ago. He keeps trying to convince her he should have another chance but that door closed months ago. That door is not only closed, it’s sealed.”

J Lo & Drake Spend New Year’s Eve Together: Dec. 31

After canceling her New Year’s Eve performance in Miami, citing “personal and family time,” Lopez was spotted at Drake’s New Year’s Eve show at a Las Vegas nightclub. The rapper’s set began just after 1 a.m. local time, and went on for about 40 minutes, according to E! News. He never acknowledged Lopez’s presence formally — but as some photos shows, the “On the Floor” singer was on her feet. The couple left through the back door of the club together around 2:30 a.m.

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Drake Gifts J Lo a $100,000 Diamond Necklace: Dec. 31

Well that’s one way to make your relationship official! Drake gifted his rumored love interest the ultimate accessory: a Tiffany Victoria necklace for $100,000, PEOPLE confirmed. Lopez wore the 17-in. diamond strand — which features more than 15 carats worth of round-, pear- and marquise-shaped diamonds set in platinum — on New Year’s Eve.

J Lo & Drake Have a ‘Flirty’ Dinner Date: Jan. 7

“Drake had his arm around her and they looked very cozy,” an observer told PEOPLE of the pair’s dinner at L.A. hotspot Nobu. “They seemed to have a lot to talk about and looked very happy together. Jen was giggling. Drake was very flirty with her and you could tell that she had a great time.”

Drake Has Met JLo’s Kids: Jan. 18

A source told PEOPLE the rapper met Lopez’s 8-year-old twins (with ex-husband Marc Anthony), Max and Emme. “Drake spends time at Jennifer’s house and of course the kids are around,” said the source.

Drake & JLo Were ‘Never Very Serious’: Feb. 9

After reports claimed the duo had called it quits, a source who knows them both exclusively told PEOPLE the entertainers were never in an official relationship. “It was never very serious,” said an insider close to the rapper. “They like one another and had fun together.”

“It was and is fun when they see each other,” the source added. “They love hanging out and making music together. [Jennifer] has great respect for him and his talent and he does for her as well.”

JLo Addresses Her Relationship with Drake on Ellen: Feb. 21

The singer remained mum on any details surrounding her whirlwind romance with the rapper while appearing on The Ellen DeGeneres Show — only admitting to “hanging out” with Drake. The talk show host then asked her guest if she seeks out younger men.

“If I like them, I like them and if I don’t, I don’t. It’s just about the person. It’s about who they are, it has nothing to do with age,” the mother of two explained.

JLo Puts the Drake Talk to an End … Once and for All: March 6

Appearing on The Daily Show with Trevor Noah, Lopez put the nail in the Drake coffin, saying, “Let me clear this up. I am not with Drake.”

She added, “Maybe that’s all I need to say.”

Of course, the very next day the JLo dating machine spun up again with news she was now seeing MLB legend Alex Rodriguez.