(cracks knuckles)
In doing an archive dive (okay, actually the WS Story Arc Summary list, but still), I think I may have discovered a primary reason why this is really bothering me - and, presumably, many of us who have been around Wapsi for a while.
Kevin is a FYC - First Year Character.
Turn your wayback machine to July of 2002 - when the strip was only 10 months old.
Monica's boss informed her that she would be working with a
"local photographer" for a museum exhibit.
Her first description of him? "Egotistical jackass."
His first description of her? "Egotistical bitch."
Oh yeah, this was going to be a love affair for the ages.
At the ensuing show, he asked her out to dinner... and
she didn't even set up a date for it.
Guess what? We don't run into Kevin again until two years later. If she wouldn't have been walking Dietzel in the park the same day
Alan and Kevin were walking along outside of work... well.
While we do see the first and second date, we have a rather long time between appearances for him. In fact, after Shel "interrupted" the two of them, we don't actually see Kevin again until he does the accidental damage in her basement in October/November of 2005. This was the first time M tried to hide the supernatural (namely the GG's) from him - which led to her
first attempt at distracting him with sex (If you need to remember which strip THAT was, you need your WapsiCred card revoked).
From there on, Kevin's relationship with Monica was pretty - um, one sided? Kevin even
mentions it to Alan in 2007. She continually chickens out in wanting to show him how she can "poit" - instead,
giving him the long tongue.
Kevin does make appearances after that - and, of course, he's the one who makes the suggestion
"Is there any reason that you have to wait until 2012 to fix it?"
Side note: I'm betting that in the previous 56 time loops, Kevin decided at this point that he had one loopy girlfriend, and booked on her. This was the first one where he made the suggestion.
Anyways - we know about the whole dancing thing with Bud, and his half-kidding comment about
"this snowman will take at least half-an-hour to build...", and of course the
"WHAT ARE YOU DOING IN MY BED?" routine.
The most telling thing? Doubt - before being distracted by Pizza - hit a nerve:
"You feel validated. You 'need' him, don't you? ...Of course you must know your worth. That's why you don't want him to leave."
Kids: this relationship was never on equal footing to start, and had portents of doom from day one. Yes, day one was 12 years ago, but that doesn't mean it was perfection.
Just my $0.02.