I very strongly feel that unreliable men don't magically reform when they meet the right girl, so I'm not sure what to think of this. Except that separate field assignments every now and then might be to their benefit.
No, not magically reform, but people do change over time. Haven't met one who hasn't. Him basing getting bored on a youthful relationship negates the growth he's done over time. And these two have had plenty of time. Plus there's the fact that while Wynston is sure that he would have gotten bored in all other cases (and maybe he would have) he has been avoiding permanent relationships for so long that he may have surprised himself somewhere else as well.
I thought his drunk overly pessimistic view of wasting time was interesting - drunk Wynston is moody and prone to melodrama lol.