Monica has two really serious relationships on Friends – Chandler and Richard – but Pete Becker comes in a close third. First appearing in season three, the two get together after a bit of a rocky start, and even reached a point where Monica thought that he might propose to her! In the end, though, he chose a (poorly considered) attempt to become a UFC champion over their relationship.

However, even if it hadn’t ended because of Ultimate Fighting, it would have ended – and most fans could see this from the beginning. Their early interactions proved that while they were fun for a time, there was never really going to be a long-term future for these two.

10 She Wasn’t Attracted To Him

A fairly huge stumbling block in any relationship is if one person isn’t attracted to the other one – and that’s what happens here. Monica knows Pete initially as a customer at the diner, and she just isn’t into him. And she later decides to try and date him a little despite the fact that she isn’t attracted to him and feels no chemistry, just in case she starts to. Terrible idea from the beginning.

9 He Asked Her Out At Work…

There’s something particularly awkward about the fact that a customer asked out a server, especially given the ridiculous costume Monica was wearing at the time. Monica was definitely struggling for cash, and didn’t do the work because she loved it, so a customer would potentially realize that she would feel pressured into being overly friendly or flirty in order to be seen as providing good customer service. Asking her out (quite aggressively, and after eavesdropping on her other conversations) puts her in a tough situation, and shows that he doesn’t really understand what’s appropriate there.

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8 …And Then Tipped Her Tens Of Thousands Of Dollars

The really famous storyline is, of course, that after asking her out, Pete tipped her twenty thousand dollars. Monica initially thought it was a cute joke, before learning from Chandler that Pete was a multi-millionaire, and it was a real check. The big issue here is, of course, that it feels a lot like Pete is paying for Monica to date him, especially given that (again), he knows she is working a low-paying job that she doesn’t love, in a cheesy diner, because she can’t get other work. It’s a power move that just doesn’t bode well.

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7 She Turned Him Down

More red flags, as Monica turns Pete down when he asks her out. Normally, being turned down would just be the end of it, but Pete continues to try and pressure her (with the aforementioned check, among other things).

It’s just not a great sign that a relationship would start with being turned down, then pressured and paid to go on a date. Not exactly instant romance!

6 And He Overcompensated

On their first date, he flew them to Rome. Plot issues aside (why did she have her passport on her? What about flight times and time zones?) this is way, way too much. Monica manages to find it romantic, but it’s just far too much, and for someone like Monica, who loves to plan ahead for every detail, it may have actually been more stressful than romantic.

5 It’s Not Clear What They Actually Have In Common

Although Pete and Monica date for a while, it’s never really shown what makes them a good couple, or what they have in common. He seems nice, and they are seen having some pleasant interactions, but there’s nothing really holding them together in terms of their day-to-day lives. They are both very driven, presumably, but in totally different ways. And Monica isn’t exactly a tech nerd, whereas Pete definitely is. They just don’t have much beyond money…

4 They Never Felt Like Equals

Becuase of Pete’s money, there was never a feeling that these two were dating on equal terms. He could change her entire life in an instant, and probably without thinking – if he can afford to fly every date to Rome, he could cover Monica’s rent for a year without breaking a sweat!

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And for someone like Monica, who is a very Type-A, driven woman, this was just not going to work. She would want to be on an even footing with her partner, and she just wouldn’t get there with Pete.

3 He Lied To Her

Definitely a bad sign for the future is lying from the start – and while this didn’t happen until a little further down the line, it was definitely a problem. After Pete bought Monica a restaurant, and she turned him down, he told her that he was dating someone else, so it wasn’t a problem. Which was a much bigger problem when it was revealed that he was lying about it, to try and convince her to take the job.

2 He Basically Bought Her Affections

This has already been alluded to a lot, but it was clearly the biggest issue from the start – Pete seemed to think he was able to just buy Monica’s presence in his life. Whether it was buying a date with a check, buying a second date with a trip to Rome, or buying more dates with a restaurant job, Pete clearly didn’t see an issue with throwing his money around to keep Monica interested, but everyone else did.

1 Having Monica Marry A Millionaire Doesn’t Work For The Show

The final reason that this would never work has little to do with the actual issues of the characters, but with the writing for the show. At this point, the characters are all still in the relatable, likable, struggling-twenty-somethings stage of life. Having Monica date a millionaire was fun, but having her actually marry him would have just derailed the premise of the show for her, and the writers weren’t about to do that.

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