First Hugh Hefner’s heart was broken by the loss of his number one girlfriend Holly Madison, who made the somewhat perplexing decision to run off with a rubbish emo magician. And now one of his other girlfriends – the equally generic titty model Kendra Wilkinson – has decided to leave Hugh Hefner and get engaged to an American football player as well.

Although Hugh Hefner seems to remain on good terms with Kendra Wilkinson, this news must have nevertheless bruised him quite badly. After all, it’s hardly as if Hugh Hefner lives in a great big house stuffed full of identical booby halfwits all willing to have gruesome, underwhelming sex with a frail 82-year-man just because they’ll probably get a minor role on a crappy reality TV show out of it, is it? Oh.

Hugh Hefner has never wanted for female company. He’s dedicated his entire life to living out a sexually progressive agenda that’s allowed him to have instant quibble-free sex on demand with any number of women who all look so freakishly similar that there’s a strong chance they’ve all been glooped out of a pulsating Alien-style egg tube.

But lately it looks as though the only female company that Hugh Hefner gets is from the women who occasionally visit to wipe his bottom or make sure that he hasn’t been lying at the foot of his stairs meekly calling for help for more than a couple of weeks at a time.

It was only a few weeks ago that Hugh Hefner’s number one girlfriend Holly Madison dumped him, started hanging around with the world’s most easily-ridiculed magician and took to bleating on about how high maintenance Hugh was. And now Hugh Hefner has been dealt another cruel hand.

It turns out that Hugh Hefner’s number three girlfriend, Kendra Wilkinson, has left him too. According to reports, Kendra Wilkinson has decided that, rather than stick around to act out each and every sexual whim of a sleazy old man, she’s going to get married to Philadelphia Eagles receiver Hank Baskett. People reports:

“[She] has met someone who she would like to spend the rest of her life with,” Hefner said in a statement on Thursday. The Playboy mogul says Baskett proposed to Wilkinson on Saturday. I have given her my blessing and will be giving her away at a very special wedding ceremony at the Playboy Mansion this coming June,” the statement adds.

Oh good. At least Hugh Hefner is going to be giving Kendra Wilkinson away. There’s definitely nothing creepy about that.

However, just because he’s lost Holly Madison and Kendra Wilkinson in short succession, it’s not all bad news. After all, he may have bid farewell to his number one girlfriend and his number three girlfriend, but that still leaves Hugh Hefner with his number two girlfriend Bridget Marquardt, who’s presumably called his number two girlfriend because she lets him stick it up her pooper.

And besides, rumour has it that Hugh Hefner has replaced Holly Madison and Kendra Wilkinson with 19-year-old twins named Karissa and Kristina Shannon. You see? Hugh Hefner will never be lonely. Thank God for opportunistic moral-free fame-hungry tit models who couldn’t give off more of a gold-digger vibe if they chopped one of their own legs off.

It hasn’t, of course – which is why we’ve still got the horn for Fidel Castro – but it did come close. For the life of us, we couldn’t work out why the pretty young topless model Playmate Holly Madison split up with a wrinkled old almost-dead pensioner like Hugh Hefner.

And now we know. Speaking about the split, Holly Madison has said that she ended things with Hugh Hefner because he was so ‘high maintenance’. And, coming from a woman who looks like she needs six hours each morning to paint herself exactly the right shade of orange transvestite, that must be really saying something.

It’s never hard to split up with someone. Finding the right words can be a struggle. “It’s not you, it’s me” would be perfect if it wasn’t such a cliche. Or there’s “I just need some me time,” except that tends to make you look like the planet’s biggest twat.

There is always “You’re just too high maintenance for me,” though, which is perfect – an equal mix between vague and scathing. Call someone high maintenance and, while they’re busy picking apart their personalities, you can skip away without revealing that you’ve actually been having it off with the girl from your badminton club.

The genius of the high maintenance accusation is paying dividends for Holly Madison. Although she found fame as Hugh Hefner’s number one girlfriend for over a year, Holly Madison recently dumped Hefner and left him heartbroken. Why? That’s right – because Hugh Hefner is apparently high maintenance, as the New York Daily News reports:

Hugh Hefner’s former No. 1 girlfriend is excited about her future dating prospects – just as long as they’re not like her famous ex. “It might be refreshing to date someone who is not high maintenance,” Holly Madison told “Extra” in an interview set to air on Wednesday. “Sorry, Hef … I love you, but you know you’re high maintenance.”

But what does Holly Madison actually mean when she says that Hugh Hefner is high maintenance? We’ve rattled Holly’s statement through the Hecklerspray Truth Computer, and here are the options it threw up:

1 - Holly Madison would like a boyfriend who doesn’t need to have his food cut up into little chunks before he can eat it and, ideally, is able to wipe his own bottom.

2 - Holly Madison would like a boyfriend who is able to get an erection without pharmaceutical assistance, three hours of manual coercing, a winch and the song We’ll Meet Again by Vera Lynn played on a loop.

3 - Holly Madison would like an elderly millionaire boyfriend who’s at least willing to pretend that he knows why she’s with him and is prepared to write her into his will accordingly.

But regardless of the reason behind the split, we hope that all this new freedom has made Holly Madison happy, and that she’ll soon be able to settle down with someone less high maintenance. Someone like her current squeeze Criss Angel, even though he looks like exactly the sort of man who’d get into a fistfight with you if you used his hair straighteners without permission.

But you know who does? Criss Angel, the magician who’d be just like David Blaine if only David Blaine a) did magic tricks any more and b) constantly walked around in clothes that made him look like an emo weekend dad having a chronic mid-life crisis regardless of how much of a ridiculous tithole everyone thinks he is.

But Criss Angel must be doing something right, because he’s Holly Madison’s new boyfriend. Word has it that Criss Angel ensnared Madison by performing a number of magic tricks that Hugh Hefner could never do, like running up the stairs, doing the Can-Can and getting an erection unaided. But can Criss Angel doze off in an armchair in the afternoon while doing some gentle Sudoku? No he can’t – Hefner will always have that.

Here’s where we’ve been going wrong with the ladies. We’re not in our forties, we don’t dress in an utterly age-inappropriate way, we haven’t got hair that we seem to have copied from a Funeral For A Friend video, we don’t wear so much pretend-Gothic jewellery that we look like a negative of Mr T at a pikey seance, we’ve never had a knock on the head that’s caused us to believe we’re actually the lead character from The Crow and we don’t share a profession with Paul Daniels.

In short, we’re not Criss Angel. Criss Angel is all of those things, and his appeal to women is as undeniable as it is completely baffling. In his time, if rumours are to be believed, Criss Angel has worked his way through everyone from Cameron Diaz to Britney Spears, all with the aid of nothing more than old-fashioned mysticism and a profound absence of self-respect.

And now Criss Angel seems to have moved onto Playboy Playmate and Hugh Hefner’s ex-girlfriend Holly Madison. It seems as though Angel’s thing is blondes with big boobs. Antony Worral Thompson must be bricking it.

Anyway, the relationship between Criss Angel and Holly Madison was more or less confirmed at the opening night of his new Las Vegas collaboration with Cirque Du Soleil entitled either Great: Magic Needed To Be More Pointlessly Theatrical, Didn’t It or Sorry You Couldn’t Get Tickets For That Beatles Show: We Hope This Will Do or something, as People reports:

Angel and Madison have been spotted kissing and snuggling over the last several weeks in Las Vegas, but remain somewhat coy about their relationship. “This is one of the most special evenings for me in my life and I can not think of a more beautiful person, a more special person, inside and out, than Holly to spend it with,” Angel said.

That would almost be sweet, wouldn’t it, apart from two main points. Firstly, we could have done without the mental image of Criss Angel exploring Holly Madison’s insides, and secondly it only seems like a couple of days ago that Hugh Hefner was admitting how sad he was when Holly Madison split up with him. It seems a bit thoughtless to rub Hefner’s nose in it by getting off with an emo gimp like Criss Angel so soon afterwards, doesn’t it?

On the other hand, perhaps this is a step in the right direction for Holly Madison. After all, there was a 54-year age difference between her and Hugh Hefner, and only a 12-year gap between her and Criss Angel. Perhaps, with a bit of time and a lot of hard work, Holly Madison will one day be able to reduce that gap to something that doesn’t make us feel a bit creeped out at all. Fingers crossed.

Apparently Hugh Hefner has been dumped his number one girlfriend Holly Madison – a woman 54 years younger than him who looks like she was reared in a battery-farm for titty bimbos – and all because Hugh refused to marry her.

Touchingly, Hugh Hefner seems quite sad about the split. There’s no need for him to be – after all, he shouldn’t forget the old saying ‘there are plenty more opportunistic young women who’ve mutilated their bodies for the sake of beauty that are willing to fellate a very old man even though it clearly disgusts them on the off-chance that he’ll write them into his will and make them rich when he dies’. Um, ‘in the sea’.

Hugh Hefner has lived the male dream to the letter. Boys, at one point or another, haven’t we all wished that we could grow old trapped in a gaudy shrine to our own sleaziness surrounded by women who are effectively paid to have a fleeting superficial interest in us in a way that keeps highlighting our chronic inability to form genuine emotional bonds with people? Well, haven’t we?

Of course we have. Hugh Hefner is a lucky man.

Lucky, but sad. Although last year Hugh Hefner vowed to settle down with his girlfriend Holly Madison, it looks like that relationship has hit the skids. Apparently Holly Madison left Hugh Hefner because he refused to marry her and she was insulted by his lack of commitment, not the way that she wouldn’t automatically get half of his stuff as soon as he dies in the next couple of years.

And although Hugh Hefner has made his career by playing Mr Free And Easy, it seems like he’s actually really quite glum about being dumped by an utterly indistinguishable sexbot young enough to be his granddaughter. AP reports:

“If Holly says it’s over, I guess it’s over… She’s still here in the house. Until a few days ago, we were still sharing the same bed… There’s been moments that I’ve been down in the dumps about all this, and (personal assistant) Mary (O’Connor) told me to cheer up and pointed out that there are girls lined up outside the front gate. At my age, that’s hard to believe, but it seems to be true.”

That’s the spirit, Hugh! Up and at ‘em again! Holly Madison may have broken your heart, but there are 50 other girls who look exactly like her, talk exactly like her and give off that exact same creepy golddigger vibe as her, and they’re all desperate to ride your brittle, increasingly gaunt skeleton until one of you dislocates something.

So pick yourself up, Hugh Hefner, down a couple of handfuls of viagra and get right back in the saddle again. You mustn’t die of a broken heart!

At least not while you’re so close to getting Miley Cyrus to show you her boobs, anyway.