ROME, Italy—It’s always nice when old friends come around, and so it must have been when Russian president Vladimir Putin stopped by former Italian Prime Minister Silvio Berlusconi’s lavish Milanese digs in the wee hours of Friday morning. Putin, who was in Milan for a two-day Europe-Asia summit called ASEM, had just ended late-night talks with German Chancellor Angela Merkel and, no doubt, needed a little down time. His sleek motorcade pulled up to Berlusconi’s pad around 1:30 in the morning and left again well after 3:30 a.m.

Putin was photographed with his suit jacket slung over his shoulder while Berlusconi waited at the door with his trusted Russian expert Valentino Valentini, who acts as a translator for the two men.

Berlusconi, 78, and Putin, 62, have shared a long and complicated bromance over the years, cemented back in 2002 when Putin’s daughters spent the summer with Berlusconi’s Russian-speaking daughter Barbara on a yacht in the Mediterranean. Berlusconi even flew to St. Petersburg laden with fine Italian wine to celebrate Putin’s 57^th birthday, shunning the King of Jordan who was on a state visit to Italy. Berlusconi has been a guest at Putin’s dacha in the Black Sea, and their close connection was even the subject of a number of diplomatic cables exposed by Wikileaks in which one American diplomat noted, “Berlusconi admires Putin's macho, decisive, and authoritarian governing style, which the Italian PM believes matches his own.”

Their relationship raised eyebrows when Berlusconi was in power. Berlusconi advocated Russia’s membership in the European Union and there were numerous allegations that Berlusconi’s companies and subsidiaries, including the Central Energy Italian Gas Holding owned by his investment group, benefited from Russian investment.

“I think it’s interesting that Russia and Italy have this strangely close relationship,” Alexander Kliment, a Russia analyst with the Eurasia Group told The Daily Beast in 2010. “And I think it has to do with three things: One is the personal connection between the two leaders; two, energy deals and banking; and three, the similarity in political cultures.”

The two have been photographed together attending extreme fighting events in Russia and chuckling at a number of joint press conferences in Italy. And then there’s the whole fiasco about Putin’s bed, in which a high-priced call-girl, Patrizia D’Addario, taped Berlusconi during a sexcapade directing her to, “Wait for me on the big bed,” which D’Addario then referred to on tape as, “Putin’s, the one with the curtains.”

Berlusconi, who has been convicted of tax fraud, is serving a one-year sentence doing community service at a home for the elderly in Milan, but he has found ample time lately to carry on his active social life. Earlier in the week, he was caught in a widely published selfie with Francesca Pascale, his 28-year-old fiancé, and Vladimir Luxuria, a transvestite who served as a parliamentarian. The three were living it up at his Arcore villa outside Milan, made famous by his orgiastic Bunga-Bunga parties.

In 2013, Berlusconi was convicted of having sex with an underage prostitute known as Ruby the Heartstealer, but that conviction was overturned this year when the courts determined that Berlusconi had not known the young woman’s age.

So, what were Putin and Berlusconi doing in the wee hours of Friday morning? Probably, as always, pretty much whatever they wanted to.