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.

Courtenay Semel – the woman who supposedly was Lindsay Lohan’s first lesbian love - is easily the ugliest creature I have ever seen. Dlisted had a side-by-side image of her next to the Grinch, and the resemblance is uncanny. Even funnier is that several British tabloids referred to her as “stunning” last week. I’m assuming “stunning” is actually British slang for “looks like she got beat up with a bat.” I mean there’s ugly where you sort of feel badly for the person, and then there’s the sort of ugly where you’re actually mad at the person for existing, and shoving their ugly in your face. Courtenay is that kind of ugly.

Semel is now dating Tila Tequila. Always a good idea. Courtenay is also apparently pretty mad that she has a mouth that looks like she’s storing a giftbox. That’s the only reason I can guess why she’s act like a complete lunatic and end up getting her ugly ass arrested on Tuesday night.

COURTENAY Semel, the wild-child lesbian daughter of former Yahoo chief Terry Semel, went on a tear Tuesday night in Las Vegas and ended up spending the night in jail. Semel showed up in the party town without new girlfriend Tila Tequila and started the night at Sushi Samba in the Palazzo with Kourtney Kardashian. “They were filming their dinner for ‘Keeping Up With the Kardashians’ ” our spy said. Later, Kardashian called it a night and Semel went out to Pure at Caesars with Vegas showman Jeff Beacher - and proceeded to “go nuts,” a spy said. “Courtenay got so drunk she was falling down. Security asked her to leave, but she refused.” Semel finally left, but on her way out there was an altercation with a security guard. “She was arrested and spent the night in jail,” a Semel pal confirmed. “And she lost her phone.” Calls to Semel weren’t returned. Vegas police said, “We can’t confirm at this time.”

[From Page Six]

Here’s Courtenay at the Palazzo Hotel’s Sushi Samba Sugarcane Boutique Club in Vegas on Tuesday. Sorry. I’ve got to attach photos, and as much as I’d like to give you something less stomach-churning to look at, it just seemed weird to put up a picture of a rainbow or spaghetti cat or something. Header of Semel with Tila Tequila at the Apple Lounge Grand Opening in West Hollywood on August 14th. Images thanks to WENN.

Courtenay Semel and her new girlfriend, Tila Tequila, on 8/14/08. Tequila confirmed to in Touch in their 8/18 issue that they’re a couple. Credit: Faye Sadou / WENN

Lindsay Lohan was living with socialite Courtenay Semel in LA late last year. There were rumblings that the two were more than just friends, but Lindsay was also dating guys at the time and she wasn’t seen out much with Courtenay.

Courtenay was said to be jealous of any other women that talked to Lindsay and moved out of the Hollywood home they shared in late January.

Semel is the daughter of Yahoo! CEO Terry Semel, and is now openly dating idiotic reality star Tila Tequila.

Apparently she’s not over Lindsay, though, because she’s resorted to talking to the UK paper that gives ex lovers of celebrities a chance to sensationalize their past - The News of The World. Courtenay told the rag that she’s perplexed that Lindsay so quickly moved on to Samantha. She’s also upset that Lindsay refused to acknowledge their relationship, but is openly dating Samantha now:

Lindsay now does little to disguise the tenderness of her relationship with British DJ Samantha Ronson—but this is only after months of covert gay experiments with stunning brunette Courtenay Semel.

Everyone thinks Samantha is Lindsay’s first lesbian love, but we were very passionate until her fear of being found out drove us apart,” Courtenay told a pal.

“At the time she was terrified her career would be over if she revealed her sexual tendencies.

“But then Samantha came on to the scene and I was dropped.”

Courtenay, 25, also told how 22-year-old Lindsay, whose films include Herbie, Fully Loaded and Mean Girls:

BEDDED a string of men in a bid to suppress her lesbian urges — and to hide them from her public.

SANK into addictions as the pressure of her double life grew.

SLIPPED into a bizarre love triangle with both women.

Courtenay’s pal explained: “She met Lindsay in the summer of 2006 at a party in Malibu.

“From the start Lindsay was very confused about her feelings for Courtenay so did more and more drugs to stifle the sexual attraction she was experiencing.

“But eventually she just gave in and at every party they’d kiss and touch each other in the corner. It’s a miracle nobody found out.

“Both of them would do lines of cocaine in the toilets then head home and fall into bed together.”

Throughout the following year, the pair stumbled through an on- off relationship as troubled Lindsay checked into a succession of rehab units and continued to date men as a ‘cover’. But it was as early as January 2007 that she first met 31-year-old Samantha, sister of pop guru Mark Ronson.

[From News of the World]
This makes it seem as if a lot of Lindsay’s addiction and sexual problems came about as she tried to cope with her feelings toward women. Of course it doesn’t excuse her very obnoxious and harmful behavior, and she’s probably still a self-entitled brat, but at least she’s relatively sober and well-behaved compared to her wild past.

Courtenay eventually left Lindsay when she kept sleeping with men and didn’t seem able to take the relationship seriously. She says that Lindsay and Samanth were just friends for a while and that Samantha often gave her advice. The article concludes by making Courtenay seem like a crazy jealous person who is unable to move on:

By October, Courtenay appeared to have the upper hand. [over Samantha] She and Lindsay moved into a rented house in Beverly Hills. “But still Lindsay brought men back,” the pal added. “Courtenay would throw fits of rage, writing her hundreds of angry e-mails from another room in the house.

“The sexual attraction between them was electric though and they’d still kiss and make up.”

That ended last December when Lindsay bedded one man too many and, unable to take more humiliation, Courtenay moved out.

It was less than a week later that Samantha was back on the scene. Outwardly, at least, Lindsay became a changed person, even turning blonde.

The pal added: “Courtenay still can’t understand how Lindsay is now so open with Samantha.

“Every time she sees a picture of them together it kills her.

[From News of the World]
Maybe Lohan just never openly dated Semel because their relationship wasn’t stable. It’s no wonder she refused to make it known that they were together when Semel was acting like that - she must have doubted it would last.

Star Magazine reports this week that Courtenay ran into Lindsay and Samantha at a lounge at bar in LA and that she “was staring daggers [at Lindsay and Sam] all night.” It looks like Tila Tequila is more this woman’s speed and that Lindsay made a wise choice by picking Sam.

Lindsay and Courtenay are shown below in December, 2007. Credit: Splash News

Here are more photos of Courtenay and Tila Tequila on 8/14 and 8/18. Credit: WENN and PRPhotos. Lindsay Lohan and Samantha Ronson are shown out at the movies and to lunch on Saturday and out for a walk on Sunday. Credit: Fame Pictures