madtomedgar:

“John and Abigail continued to worry over their son’s [Charles’s] alcoholism, and they were outraged when he squandered some of John Quincy’s money that had been entrusted to his care. But something else concerned them as well, although their correspondence and that of Charles’s siblings contains only dark hints and allusions with regard to this other, unspecified behavior. There are references to his alleged proclivity for consorting with men whom his parents regarded as unsavory. John Quincy, who remained a close, tolerant older brother through thick and thin, urged Charles to “be more cautious” and prayed that his conduct would remain within “the limits of regularity.” By the early 1790s, such references may have been occasioned by the fact that Charles was living in New York with an old revolutionary war general, Baron Friedrich von Steuben, who is now thought by some to have been homosexual. Charles clearly adored Steuben – “My dear Mamma there is something in this man that is more than mortal,” he told Abigail – and he was grief stricken when the old man retired to a farm in upstate New York. Following Steuben’s departure, Charles announced his intention of marrying Sally Smith, the sister of his brother-in-law Colonel Smith. Whereas his parents often interceded in John Quincy’s and Thomas’s matrimonial concerns, the vice-president and Abigail seemed almost relived at their son’s decision. Even Nabby breathed a sigh of relief. After “all the Hair breadth scares and iminent dangers he has run, he is at last Safe Landed,” he exalted.”

— John Ferling, John Adams: A Life (via publius-esquire)

Charles also had a long history of extreme emotional fragility and a strange and persistent childishness. He was very wont to court multiple girls at once, none seriously, and, as his money issues show, tended to befriend people who then manipulated and preyed upon him.