It must suck to date Lindsay Lohan. Aside from the obvious reasons, which we won’t even get in to. No one likes to think about their current partner’s past. In fact we all know it’s polite behavior to generally assume they never loved, liked, or kissed anyone until you came along. Then all of a sudden it was like a rush of hormones and they discovered all these previously unknown emotions.

But that’s pretty damn hard when three quarters of Hollywood knows exactly how many freckles your lady love has on her lady bits. Thus the dilemma of being Samantha Ronson. While dating Lohan has some obvious advantages – including increased career exposure for the deejay – as someone who does the music at the very best parties, the odds of running into some guy that Lindsay use to… well… [insert various filthy act here ______]… are pretty damn high. And several previous lovers all came together to make Ronson and Lohan feel damn uncomfortable at a party recently.

Talk about awkward: Lindsay Lohan was celebrating the grand opening of West Hollywood club Apple Lounge with Samantha Ronson on August 14 when she ran into two ex-boyfriends – and an ex-girlfriend! “Lindsay chatted with her ex Harry Morton for a few minutes,” a witness explains about the first encounter. “Sam wasn’t thrilled.” Lindsay, 22, was there to support her live-in galpal, who was deejaying the event. But before the night was over, another of Lindsay’s exes, Calum Best, showed up, followed by former girlfriend Courtenay Semel. Although Lindsay’s rep says, “It wasn’t awkward for her to be with all of her exes,” a witness says, “That was definitely enough drama for Lindsay. She made sure the rest of the night was very mellow, drinking little as she smoked and stuck by Sam’s side.” “Lindsay reassured Sam,” a witness says, “by gently rubbing her lower back whenever they were alone.” Courtenay Semel dated Lindsay in late 2007, says an insider. Lindsay dated Calum Best for three months in 2007. Harry Morton romanced Lindsay in 2006.

[From In Touch]

I love how In Touch is polite enough to say “romanced.” As though anyone, guy or girl, has ever bothered to slip even the slightest notion of romance into a relationship with Lindsay. Here is what qualifies for romance to a Lohan: “Oh you didn’t slip any GHB into my drink? That’s so thoughtful of you! Sure I’ll take my panties off.” Roses and chocolates are not required.

Here’s Lindsay Lohan, Calum Best, Tila Tequila and Courtenay Semel at the Apple Lounge Grand Opening on August 14th. Header of Lohan and Samantha shopping yesterday. Images thanks to WENN.