The question in the title should stand on its own so if you wish to skip the story below feel free. It's merely a qualifying anecdote that cause be to think about something brought on by an ongoing situation with some people I know. For the sake of the story, let’s call them Ivy and Brian.

Anyway, one day they got to talking and he invited her to hang out one-on-one. Not long after he soon confided in her the details of his relationship history. His most recent ex was a girl (Amy) he’d had a crush on for a while whom, almost from day one had very low level interest but warmed up enough to him to accept his offer of a relationship pretty quickly for unknown reasons (I think it was because they’d slept together and “muh reputation”, Ivy suspects it was more of a “well I don’t have anything else going on right now soooo” sort of thing). She was high maintenance, rarely available and, shall we say, “financially conscious”; sex was infrequent but satisfying when it occurred. She ended up calling it off citing a change of heart.

The girl before her (Heather) showed more interest in him initially but still had a sort of frigid, bitchy attitude. LTR status happened fairly quickly here as well. The sex was frequent but your run-of-the-mill starfish/duty sex almost from the onset and there was a lot more she “didn’t do” in the bedroom than what she actually did. She was often naggy and hyper-critical and remained the same throughout. She cheated on him with an ex, left, came back and left again.

Now, backstories out of the way, Ivy has been going out casually with Brian for a bit now and has become interested in the idea of an LTR– for unknown fucking reasons tbh. However, he claims he’s tired of disappointment and basically wants to not make the same mistakes he has in the past by jumping into an LTR full steam ahead with girls who basically did nothing for it and it almost seems as if he wants Ivy to additionally “prove” her worthiness as LTR material as opposed to making things official with her at the rate in which he’s done in the past.

On the one hand, that seems logical because it suggests he’s learned from past mistakes and is being more careful about these sort of things because that kind of disappointment happening over and over sucks; on the other, he’s recently let it slip to someone that he gets along better and feels stronger mutual interest between them than with his last few girlfriends. So, it seems absurd and unfair that he basically wants Ivy to bend over backwards to “get” a relationship with him when previously, he LTR’d all kinds of (often) awful women basically at the drop of a hat. Ivy, is getting impatient and considering parting ways but more importantly, she’s quite upset.

TL;DR: See title question.

TL;DR II: My good friend is interested in our mutual friend who is reluctant to make things ‘official’ with her due to having previously been burned by other girls while making her jump through increasingly complicated hoops to prove she’s “LTR-worthy”. Is she right to be upset?