This is one of those moments where both you and the woman you’re critiquing are right. Email #4 is an idiot. Let’s say the guy is salvageable, for sake of argument. [He’s not.] Here’s where he’s gone wrong.

1. The girl he’s chasing is too old. Given he’s 48, I recommend the old rule of “half your age plus 7 years.” For this guy, that’s 48/2+7=31. Ignore anything older. [Edit: older women are acceptable, but one should comprehend that such women don’t see themselves as mistresses. This context is too complicated to explain here.]
2. If married, never get involved with a mistress who occupies your mind. If you’re already married with children and have a mentally rewarding life, you don’t have mental energy to spare on your own fixations. Women provide enough of their own.
3. Never go to her place. Ideally, she ought not have a place of her own. If you’re intending to keep two women, you ought afford them both, else your mistress may be somebody’s girlfriend, too. You’re not sharing your wife; why share your mistress?
4. Only very financially secure men ought ever try this game. You must be so rich, and the mistress so beneath your wife in station, that there is no chance your mistress can outclass your wife. Email #4 is interested in an office girl. Unless she’s a bona-fide sexretary, she’s almost certainly career-minded. For a married guy that’s already bought one cow, the next purchase needs to be a goat. Sure, it can be a pretty goat, but it better be a goat. Low maintenance and little aspiration are key here.
5. Some girls aspire to success in marriage as well as career. Don’t pursue such girls as mistresses. They’ll always be after your wife and your estate. Pick girls who self-select out of high-society. These days, that’s the chick at the tattoo parlor with a nose ring who drives an old pick-up. The waitress who’s worked the coffee shop for two years. These chicks are looking for a beta by working-class standards. Men who can afford mistresses look beta to girls who might otherwise date bikers and longshoremen and other laborers.
6. Be clear the relationship is at will but up for renewal. If you become suddenly cash-poor (it happens), you dump the mistress. Do not the wife: such is cost-prohibitive.
7. Yes, your wife should know about your mistress and vice-versa, but that’s about all the contact they have. Neither dictates your schedule, and any children by either are their day-to-day concern to manage under your approval.
8. Mistresses aren’t cheap, even if they’re “cheap.” Realistically, your gifts are their retirement money. You can’t skimp on jewels and gold. If you’re married, you know $10,000 per year is chump change for modern women, so plan accordingly. Refer to #4.

Don't bother.

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