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But that doesn't mean that the man has remained utterly celibate and dateless. Somehow or rather despite his determination to mourn the man he lost, Will still manages to get dates in a variety of ways - usually with the help of his ill-meaning friends.
So far, Will remains single and eligible in New York. And rarely dates. A single, eligible gay man dateless in NY? Amazing but true!
Wealthy, obnoxious and arrogant, Nathan Berry is a highly successful New York publicist who drops first names at every turn. Armed with loads of cash, a lot of hot air and an empty apartment, he arrives on Grace's doorstep in search of a decorator and gets designs on the decorator's gay roommate instead. In order to secure Nathan's contract, Grace has to be sacrifice poor Will on the altar of Nathan's wicked intentions. Saving Grace, Will decdies to go through with it and finds that not only didn't he begin to like the man, he starts to detests him further. Which only makes the man far more interested.
However it is Will’s first real date after his ‘relationship with Michael’ so the man starts getting jittery – especially when Richard calls to say he’s running late – which is supposedly gayspeak for ‘I'm blowing you off’. But all ends well and the excuse is valid as the Borders hunk appears at Will’s doorstep - with bells on and muscles bulging.
Obviously tired of matchmaking for her daughter Grace, Bobbi Adler decides to try her skills on the unsuspecting Will. A childhood friend of Grace’s, Andy Fellner went to camp together with her and paticipated as Woodchuck Number 2 in the recreation of Noah’s Ark. Grace begs Will to agree in the hopes that the blind date would end up as a disaster therefore curbing her mother’s matchmaking. However, the lil woodchuck has grown up pretty well and Will soon has the opportunity to find out just how sharp a woodchuck’s teeth are. However Will’s plans with the cute woodchuck for a lil whack, bang, wiggle-wiggle totally fizzles out as an irate Grace – who’s irritated at the fact that Will and Andy are hitting it off proving her mother correct - keeps interrupting.
For some reason, people love finding dates for single gay men – meaning Will. Even his boss gets onto the bandwagon when he suggests that Will go out with an old poker buddy of his who happens to be gay. However the first date turns out awry and Will is incensed when everyone says that he is a lousy first date - especially when Charlie doesn't call him back.
The infamous man who dumped our poor Will Truman after 7 years! Talk about a seven-year-itch! Not only did the man supposedly dump him, he also left Will with nothing but a broken heart and a couple of love handles. After disappearing for some time and leaving Will but half a man, Michael suddenly makes a reappearance in downtown Manhattan - and asks Grace to decorate his townhouse. The loyal Grace tries to hide it for fear of Will's reaction but he seems fine with it when he finds out.
Although he acts nonchalant about it, it is not long before Will starts overreacting to the fact that his ex is back. It seems as if Will might NOT have totally gotten over his ex-boyfriend and starts getting the idea that Michael is back for him. Recollecting their past, he starts getting mushy and remembers the clock that they first bought together and the matching I can't even think straight T-shirts. It all ends not very well however when after all Will's soul-searching, he finds out that Michael is already seeing - and has been seeing another man since they broke up.
Neil is Will's mother's dentist's bridge partner's son... which obviously makes him eligible for a date with Will. In the beginning, Will does this as a favour eventhough he doesn't think much of the smarmy Neil - who thinks of himself as God's gift to gay men. In a bid to get out of the date, Will even made a pact with Grace to save him by calling him away for a falsified emergency.
According to rumours, a new man might be playing a significant role in Will's life not very long from now. I guess it's time for Will to have a leading man. And who else better than the personable sports writer Matthew who evidently does 32 long flat chinos real justice. A regular shopper at the Banana Republic, Matthew is quickly scoped out by the ever observant Jack. Enamoured with Matthew's obvious manly charms, Jack quickly makes a play for him. Unfortunately the usually gregarious, garrulous Jack is turned tongue-tied in the presence of such amazing testosterone. The fact that Matthew is a smarty who uses words with more than syllables also scares Jack to pieces.
Who could resist a line like that? The perspicacious Matthew finds Will fascinating and gives him a number - his home number no less. Thus rejected, Jack obviously moves on to greener pastures and better beef with alarming alacrity. Although the charming Matthew makes the first move, it takes a while before Will drums up the chutzpah to reciprocate. However, the two hit it off incredibly well despite Will desperately trying to impress Matthew with his meagre sports knowledge. All seems to go well until the issue of the closet comes into play. Matthew's still in the closet. And Will's reluctant to enter the dingy closet again. Things get worse when Matthew, still reluctant to out himself, starts introducing Will as his own brother. At the same time however, Matthew sweetens the pot by confessing his budding feelings to Will. Torn by his need to be true to himself and yet falling slowly for Matthew, Will finds himself in a quandary.
Obviously on the rebound from the irresistible Matthew, Will starts dating a man called Paul all for the sake of his big dog. A well-trained, kissable dog. You'll be forgiven for thinking what you're thinking but it IS actually a big dog. It's love at first sight as Will tumbles heads-over-heels in love with Pepper, Paul's St Bernard dog. But although Will loves sharing kisses with the hairy dog, he prefers not to share with the dog's owner, Paul. But for the sake of Pepper, he continues their relationship.
While Will is moaning and groaning about not having a man, he never notice dthe looks he's actually getting from other men. Not even a blatant come-on fazes the man and he is non-plussed when he finds himself the target of another man's attention... Drowning himself in liquor, Will is suddenly approached by an attractive... much, much younger man.
Of course being the typical ageist that he is, Will tries to keep his cradle-robbing affair a secret from his prying friends. Which isn't exactly Will's fault especially since people keep asking about how to get involved with the Big Brothers of America when he's on a date with Scott.
Neil is Will's mother's dentist's bridge partner's son... which obviously makes him eligible for a date with Will. In the beginning, Will does this as a favour eventhough he doesn't think much of the smarmy Neil - who thinks of himself as God's gift to gay men. In a bid to get out of the date, Will even made a pact with Grace to save him by calling him away for a falsified emergency.
Though it has never really been proven, there has been signs that his friend Jack had more than a passing interest in Will. Although he tries to hide his feelings with tubby jokes about Will's weight, there have been several instances when Jack seems to care more for his friend than they both knew.
JACK: Steven was a guy at his old law firm. They had a little fling last summer while he was still seeing Michael, and let me just say Hottie...McHot. Ssss...
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Which obviously drags Will into the picture. In a Cyrano de Bergerac plot, Will provides a front for Jack in wooing Matthew. However it turns out Matthew has far more in common with Will - and has far more brains than expected as the man easily finds out that Will is providing Jack's honeyed words.
