Love and romance is as big a part of Younger as the idea of Liza trying to pass as a millennial post-divorce, whether it's her love triangle with Josh and Charles, Kelsey's search for the love of her life, or Diana's struggles with loving a plumber. Dating isn't easy in New York City, no matter what age the characters are, and everyone has their ups and downs as the show goes on.
The upcoming final season of the show is undoubtedly going to answer fan questions about who Liza ends up with (and whether #TeamJosh or #TeamCharles will win), how Diana will deal with married life, how things will work out for Kelsey and Zane, and if Lauren will find someone who doesn't bore her. Along the way, there are sure to be a few more questionable choices in romance, too, but who knows if they'll be worse than these choices - which definitely had fans raising their eyebrows.
10 Kelsey Dating Her Author
Kelsey's first major book as an editor was one she worked hard to get - Anton Bjornberg. This Swedish author was a huge get for Empirical, and Kelsey was thrilled to be able to work on the translation of his book with him. However, she also decided that it would be a good idea to have an affair with him, a choice that would put her job and her reputation as an editor on the line. On top of which, Anton was married, and his wife was furious when she found out.
9 Green Card Wedding
Poor Josh doesn't have much luck with love - even though he would do anything to make his relationships work, including getting married! When he fell for Irish bartender Clare, he was devastated when she had to return to Ireland, and flew out to visit her. So far, so understandable. However, they then decided to get married so that she could get a green card, even though they had only known each other a few weeks! This didn't work out, unsurprisingly.
8 Kelsey & Colin's Whole Relationship
Kelsey really does seem to have a bad habit of sleeping with her authors - and letting men walk all over her! Colin seemed like a charming writer, at first, but it quickly became clear that this relationship was just a series of questionable choices. First up, Colin asks Kelsey to 'look over' his book almost as soon as they meet, which should have been a red flag from the start. However, Kelsey then makes the choice to look over it and basically re-write it into something that will become a hit - she secures its success (but not for her own company), even though it's definitely not a good idea. In the end, there was no way this would work out.
7 Catfishing Diana For A Handbag
There was nothing questionable about Diana's choice to look into online dating, and try to connect with a man that way. However, her the choices her 'date' made were definitely eyebrow-raising, as he was actually a teenager just desperate to handle her designer bag (and no, that isn't a euphemism).
The kid essentially catfished her for the sake of his fashion blogging.
6 Kelsey And Tram Sex
Another scenario that seems to be one questionable choice after another comes when Kelsey hooks up with a new guy through 'Handlebar'. Everything seems perfect, until she discovers that he lives on, gasp, Roosevelt Island. Her first questionable choice is ditching a fantastic, single, interested partner because of where he lives (even somewhere as disconnected from the rest of Manhattan as Roosevelt Island). However, her far worse decision is to not just have public (and extremely visible and illegal) sex on the tram, but then refusing to even step foot on the island itself. It's a pretty terrible way to treat a decent guy, whose only fault is his address.
5 Office MakeOuts
Yes, it may be sexy, and is supposed to show just how passionate Liza and Charles are - they just can't keep their hands off each other! However, a makeout session in the boss's office, with the boss, while the cleaner is doing the rounds, is just too risky. Liza's relationship with Charles is fraught to begin with, and this was just too potentially problematic.
4 Hate-Dating
Kelsey and Zane are a complex pair. They seem to be great together... sometimes. They certainly have chemistry, they have similar interests, they challenge each other, and they want each other. However, their dating decision is always a little questionable, because a lot of their chemistry seems rooted in competition and even outright dislike.
Zane tries to poach clients, to start up a competing business, and to spend a lot of time smirking and Kelsey and attacking her under the label of 'challenging' her. It remains to be seen if this works out in the final season, but it's definitely one that fans are questioning.
3 Kelsey's Networking One-Night-Stand
There's nothing particularly questionable about a one-night stand, especially in this show. However, when Kelsey is still furious at Liza for lying to her and recovering from a break-up, the night she sleeps with a stranger at a networking event is definitely not the smartest move. For one thing, getting all-night wasted at a professional event isn't the best look to begin with, and having casual sex with someone that may actually be a professional connection in the future is just asking for trouble.
2 The Lip Shaving
For the most part, Maggie has possibly the healthiest romantic life of anyone on the show. She enjoys her flings and her fun, and her relationship with Malkie was one that stalled over the kids question, but seemed to be dealt with in a mature and reasonable way. However, possibly her most questionable dating choice was with a woman she met at an art show, who had hair on her upper lip. Maggie, rather than decide not to date someone she was not attracted to (which would have been the smart move), decided to try and date her anyway, focus obsessively on the lip, and then try and shave it for her while they had a bath together.
1 Liza, Don, And The Dine & Ditch
Liza may be playing at being a millennial, but she should know enough to act like an adult - and choose her confessions wisely. However, she throws caution (and courtesy) to the wind with journalist Don. On their date, not only do they decide to dine and ditch (or at least, part pay and leave no real tip) - a choice that is not just going to end up with the server paying for them (most likely), but is totally unnecessary, seeing as Liza could easily have paid the bill in full, with a healthy tip. Then, Liza reveals all to Don, even though she barely knows him, and he is a journalist. Unsurprisingly, this ends up causing all kinds of trouble.
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