Leland saw an opportunity with Cheryl because she appeared to be intelligent and professional in her job. She had something that went beyond the plastic personality he found in most of the other women with whom he worked.
Cheryl was intrigued by Leland. She, of course, had not known him as the scrawny pimpley guy he'd sort of naturally outgrown. At this point in his life, Leland graduated to simply not good-looking.