On episode 9, season 20 of The Bachelor, Ben Higgins and his final three: Caila, JoJo and Lauren B., took their relationships to the next level in Jamaica. After several weeks of deliberating if they should or shouldn’t, all of the women admitted they were in love with the Bachelor, Ben found himself returning the sentiments to two of the women, leaving the third out in the cold. As if having his heart being tugged in different directions weren’t bad enough, Ben had to break one unsuspecting bachelorette’s heart. Here are a few times we knew Ben–and the ladies–were, and are, heading for heartache.

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1. Ben and Caila Share an Awkward Day

TheBachelor-133.jpgGoing into their date, Ben’s biggest concern was that the perky brunette was all show and no go. Caila was apprehensive to put herself all the way out there, since the man of her dreams also happened to be dating two other women as well. Their jungle river cruise was an exercise in awkwardness, as Ben tried to make small talk, and Caila failed to maintain her signature perkiness. Not even cocktails served in coconuts were enough to break the ice.

2. Ben Doesn’t Say the Words

TheBachelor-177.jpgAfter a lackluster day together, Caila knew she had to deliver a ratings-worthy moment, and, of course, disclose her deep feeling for the Bachelor. With some gentle prodding from Benjamin, Caila finally told the Bachelor she was in love with him. Fans knew, thanks to an abundance of spoilers, Ben said the L-word to two of the ladies, so when Caila got crickets, viewers knew the relationship was doomed. Not that Caila was the least bit phased by Ben’s failure to reciprocate. She was confident that Ben felt the same based on his body language and the look in his eyes. Can someone please get this woman a copy of He’s Just Not That Into You, stat!

3. Ben Says “I Love You”

TheBachelor-384.jpgLauren B. has been head over heels for Ben for a while, and like Caila, she knew it was time to put up or shut up. The pressure was on to declare her love, because we all know it’s more acceptable to spend the night with a man on national television if a woman is in love. Riddled with anxiety and insecurity, especially not knowing where “Big Ben” stood with her competition, Lauren B. delivered a monologue the length of a Bible outlining all of Ben’s attributes, and Ben was all ears. At long last, Lauren B. told Ben she was in love with him, and much to her surprise, if nobody else’s, Ben admitted he felt the same way. This revelation was bad news for Caila and potentially bad news for JoJo as well.

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4. Ben Drops the L-Word, Again

TheBachelor-490.jpgAfter spending the night with Lauren B., and uttering a nauseating amount of “I love yous,” Ben had to turn his attention to JoJo. Lauren B. may have had his heart, but Ben wanted the chance to sort out his feelings for JoJo. As soon as he saw her in her skimpy denim shorts, Ben was reminded of their smoking-hot chemistry. The two took a helicopter ride to a remote waterfall where they took the plunge literally and then metaphorically. JoJo told Ben she loved him and was shocked when Ben said it back. JoJo got her affirmation more quickly than Lauren B., which could be because she spoke up sooner, or because she looked better in her teenie-weenie bikini.

5. Ben Has Doubts about JoJo’s Family

TheBachelor-547.jpgBen and JoJo may be in love, but the course of true love never runs smooth, especially on The Bachelor. Ben still had reservations thanks his disastrous hometown visit with JoJo’s family, specifically her brothers who failed to welcome Ben into the family fold. Ben filled JoJo in on the tense interactions between himself and her siblings. JoJo worked overtime to put Ben’s mind at ease, promising him that her brothers would eventually come around. Ben felt better after their chat, but we all know her brothers are maybe the only two people on earth who think Ben is a major D-bag.

6. Ben Spends the Night with All Three Women

TheBachelor-407.jpgIt’s possible that what went on behind closed doors between Ben and the three women would only warrant a PG-13 rating, but it’s far more likely we’re looking at a solid R or NC-17. In the real world, sleeping with three women in one week would be considered anything but romantic, but the Bachelor gets a free pass, because planned intimacy, right before the big finale, is a must. Granted, these are big girls, and everybody involved is a consenting adult, but it’s a tad shady and a little gross, knowing Ben Higgins ¬†dipped his wick at every available opportunity.

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7. Caila Surprises Ben

TheBachelor-694.jpgStill basking in the afterglow of her night with Ben, Caila decided to drop in on her “boyfriend” to remind him what a great couple they made. Giggly and as excited as a kid on Christmas morning, Caila had zero clue that Ben was busy contemplating how to tell her she would make a great wife, to someone else. Ben has a horrible poker face, so it didn’t take long for Caila’s mood to go from jubilant to somber. It was Caila who got the biggest surprise when Ben revealed he was, indeed, in love with two women, neither of which was Caila.

8. Caila Calls Ben Out

TheBachelor-734.jpgOnce you get dumped by the Bachelor, standard protocol is to climb into the dark recesses of a luxury car and ruminate about what went wrong. Caila was all set to do just that–and did later–but she decided to jump out of the vehicle just before it pulled away. With nothing left to lose, Caila decided she wanted to confront Ben. You had to read between the pauses and unfinished sentences to fully grasp Caila’s grievance. The gyst was Caila was a bit put out the she “put out.” It’s possible I misinterpreted their completely incoherent exchange, but I REALLY don’t think so. Ben saved some face, declaring he had his epiphanies about JoJo and Lauren B. in the moment, and his heart couldn’t catch up with certain other body parts when it came to Caila. She crawled back into the car devastated..

9. JoJo and Lauren B. Size Each Other Up

TheBachelor-815.jpgBoth JoJo and Lauren B. went into the final rose ceremony feeling very confident. After all, when a guy tells you he loves you after just a few weeks of dating, a fairy-tale ending has to be the final outcome, right? As the completely unnecessary ritual progressed, it started to occur to the final two that Ben could be in love with them both. Since Ben can’t have his cake and eat it too, and polygamy isn’t legal, one, or possibly both, of the bachelorettes are in for a world of hurt.

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The Bachelor season 20 airs Mondays at 8pm on ABC.

(Images Courtesy of ABC)