Let's do a little deep dive. Skip this if you're not a Shep fan like me.
I Drink Therefore I Am
We've been watching this guy on TV for a decade now. He's the heart of the show. What happened to the affable unassuming guy we first met? Shep was 33 then and still on track for a normal life. Yes, he was already a privileged partying womanizer, but he also had a job (real estate, I think) and a modest outlook on life and himself. Southern Charm blew that all up.
Finding himself a local and online celebrity was more than Shep's ego could handle. The free money also enabled him to justify a life of luxury he was not previously pursuing, at least not to that degree. Shep's moneyed background is often advertised as the cause of his indolence, but he went to good schools and had jobs before the show. The caricature of an entitled trust fund baby is not real life.
Like most children of privilege, Shep likely grew up with an expectation of adding more success to the family legacy. Sure, there's plenty of nepotism and debauchery along the way, but children of the rich usually go on to their own high-status achievements. Shep's sister and brother are a testament to the real life he was expected to live.
Like a moth to a flame, Shep could not resist the trappings of reality TV stardom. He gave up on any greater purpose and opted for a life of hedonism, although he painted it as a noble pursuit of new experiences. In part, he chose dilettantism because it meant less work - Shep is lazy - but it was also a guard against failure. Southern Charm became Shep's excuse to not even bother, lest he find out he wasn't good enough.
Listen to any of Shep's interviews outside of the show. He is extremely defensive when the subject of his futility is raised. If he was content with his expedient lifestyle, he would not be so sensitive to criticism of it. The lad doth protest too much.
This professional malaise extended into his personal life. Easy girls obviated the risks of real rejection. Dating quality women would mean seeing how underwhelmed they were by his fruitless life. Better to stick to 23-year-olds wowed by his words and worldliness. Shep lacked the discipline to change course on his own, but not the self-awareness to know how pathetic he’d become.
That's where drugs and alcohol come in. They help silence those gnawing voices inside telling you you're capable of more, or at least bred for more.
Love Me Bender, Love Me Sweet
For all her faults, Taylor gave Shep a chance at redemption. Because she was so lax, he didn't have his usual excuses for running. She put up with a lot of bad behavior in the early stages of their relationship, knowing it was the only way Shep would stick around. After so many years of self-indulgence, he had grown allergic to anyone holding him to account.
Nevertheless, once he was fully committed, he welcomed the calm. He admits on the reunion that he was at his happiest when he was with Taylor, even adding that they might have wed if not for the show.
There it is again. The show. It's such low-hanging fruit, and Shep is a sucker for temptation. The real mailbox money is the show. Throw in drinking and it gives Shep the alibi to succumb to his basest instincts, and to silence his best instincts, which are myriad in spite of it all.
Bravado-Con
You'd like to think that Bravo-Con crystallized for Shep how low he had fallen. All those desperate Housewives with their plastic surgeries and plastic existences would drive any man to the bottle. That’s why they’re all divorced.
Sure, Shep partied too hard in Vegas, but maybe there was an epiphany too. Scanning the room, did he finally realize what a lowbrow crowd he'd fallen in with?
The equally low caliber of fans would only reinforce the point. Shep will always be a snob at heart, and you hope the crassness of this realm finally rang his inner white trash bell. He hates Trump so much because he is disgusted by his followers, but Shep's fawning throngs are the same philistines, albeit sporting different bumper stickers.
Shep knows on some level he's better than this. It's the good kind of elitism, an antidote to the anti-intellectualism that pervades our culture. A man of Shep's upbringing should chafe at this mass of troglodytes, but also the life they have bought him.
If he removes the drinks and drugs from his life, he may actually have to face that sobering reality. That would mean quitting the show, along with its attendant money and fame.
Righting the Shep
There is always the possibility that as a seasoned TV star, Shep is just playing up a new storyline for the cameras. Maybe this cry for help is no different than Austen's fake therapist.
Assuming it's not, the answer is clear: sober up and leave the show. Find something to do. What about flipping a house? Shep considers himself a man of taste, and he can afford the financial risk. Nothing makes a man feel more like a man than building something with his own two hands, or at least overseeing men building something with their own two hands.
In theory, if Shep can point to actual professional accomplishments, it should lead to more confidence in his love life as well. If he is no longer embarrassed by his listlessness, he will feel deserving of a good woman rather than the tramps he usually settles for. With that comes meaning and happiness, same as for everyone else.
Impulse control will certainly come into play, but Shep showed with Taylor he is capable of fidelity. Whatever slip-ups he had with her, they were mostly alcohol-induced and intermittent. He can do better. He just has to admit he wants to.
Way back, Cameran was lamenting Shep's deteriorating state. She said she wanted him to turn things around before he became Thomas. 43 is late in the game, but not too late. Shep always had more potential, integrity, intelligence, and charm than Thomas. Here's hoping he rights his ship, even if that means I never get to see him on my TV again.