Not -- I hasten to add -- the most wanton, cruel or indifferent, but
specifically the most ambitious but inept, well intentioned but
bumbling, or solicitous but dull. This may encompass wooings at
balconies, strivings in the bedroom and attempts at gift giving and
poetry writing; you may, of course, go beyond any of these categories
to make your case. I'm looking for the widest imaginable gap between
effort and effect (or result). To prevent suicides and lawsuits, the
candidate must be dead at least a decade and his or her romantic
bungling should be backed by hard (or not so hard) evidence. Who does
the world say tried the most passionately and failed the most
dismally?

I vote for Victorian writer & critic JOHN RUSKIN. On his wedding night
he was so freaked out by the sight of his wife's pubic hair, the
marriage was never consummated.  (Up 'til then he'd never seen an
actual nude woman.  Only paintings and statues with smooth, un-hairy
genitals.)

While I was researching a novel a few years back, I came across a
story you might like.  It is a sad, very believable story, though I
can offer you no proof, since the story teller is certainly dead and
the subjects have both been dead longer than I decade.  I was setting
my novel in the 1940s and it revolved around a family with 2 children
and a drunk for a mother.  I needed some material to flesh out my
parents.  So using a connection at a VA hospital, I set up a couple
interviews with a few patients.

I went to see Mr. Gensch, but was sad to see him sound asleep when I
arrived.  Just as I turned to walk out of the room his wife entered. 
After explaining my situation and the appointment I had setup with her
husband she ushered me into the lounge and told me about her mother
and father.

Neither the mother nor the father got on very well together.  Father
felt as though all mother did was sleep and drink.  Mother just wanted
for father to stop trying to get her to stop drinking.  Mrs. Gensch
mentioned that father earned a decent wage at a factory making chairs
and tables, but due to the habits of mother (stealing money for
alcohol, breaking household items, selling items off) they did not
live very well at all.  Mrs. Gensch and her sister were very upset
about the family situation.  Her mother was a drunk, her dad was
always at work, and her brother was in jail.  The two girls approached
father and pleaded with him to fix the situation.  He promised to do
so.

Mrs. Gensch said that she never did understand the logic behind her
fathers attempt to fix things, but she explained it like this.  Father
came home with a bottle of Black Label Johnnie Walker Scotch (a nice
12 year old scotch), one red rose, and one white rose.  Mother was no
where to be found, which was not unusual.  He placed the roses in a
glass on the counter and hid the whiskey in the stove!  I asked Mrs.
Gensch why the stove?  She explained that mother had alcohol hidden
all through the house and thought that father figured there was no way
she would find it on accident in the stove.  Later that night Mrs.
Gensch was woken by a terrible scream.  She ran in the kitchen with
father and her sister to find mother lying on the floor bleeding and
crying.  Father grabbed mother and rushed her to the hospital.

What happened was mother came home and the kitchen was cold, so she
threw open the over door and turned it up (my family used to heat our
kitchen with an open stove as well).  She poured herself a drink and
sat at the table.  The bottle heated up, exploded, and threw a large
piece of glass out catching mother in the cheek.  Mrs. Gensch said her
mother, who at the time was a beautiful woman, was terribly scars
after.  The family never did rightly recover from the mishap.

Hope this helps, sorry this comment is so ragtag, but I have to run. 
Let me know if you need more clarification, I will dig out my notes
and find more detail.

Vern

For sheer ineptness, it's hard to beat Miles Standish, who was
reticent to court Priscilla Mullens himself, and asked his friend John
Alden to do the wooing in his behalf. Priscilla ended up marrying
John.

http://www.iamoconf.xroads.net/Globetrotter3/6Colonies/priscillam.htm

Oh dear, I hate even remembering about this poor couple I heard about
from a friend who worked in an emergency ward. They were a young
couple whose culture dictated that although living in London in the
late 1970s, their marriage had to be arranged and they were both very
accepting of this and eager to make it work, as you do. Not many days
after the wedding, the young wife was brought in with great pain in
her abdominal region. Upon examination, her belly button and
surrounding area was bruised, swollen, infected and very, very sore.
When asked what on earth had happened, it turned out that although
keen to consummate their marriage, neither one had any idea on 'how
things were done' and they assumed that sexual relations took place
via the belly button. Ouch. Doesn't bear thinking about, does it?
Happily, a few things were explained to them, they apparently
practised diligently and produced a couple of children in the ensuing
couple of years.

Stressed Mom, 

I wonder if this is an urban legend, since I heard it in another part of the world.

I, too, heard the "navel destroyer" tale in another part of the world.
The version of the story that I encountered was supposed to have
happened to a couple of hillbillies from the Ozark Mountains in
western Arkansas.

I thought of a candidate, but I guess he doesn't fit the description
of people who are already dead. Imagine a very famous person,
admitting in his recently published autobiography, that he slept with
hoards of women. However, this person is single at the moment. Do the
math:
- Slept with about thousand women (according to his accounts). 
- Very rich, and a celeb, which means that staying true to him would
be, even according to "rational choice" calculations, a good idea.
- None of these thousands stayed too long with him.

To add to the list, the Guardian have picked their worst lovers: Simon
Jeffery. "Fifteen ways to leave your lover " THE GUARDIAN,  July 29,
2003 http://www.guardian.co.uk/international/story/0,3604,1008140,00.html

You're kidding? You heard this too? Gosh, you can't believe anything
you hear, can you? To be honest, I am actually relieved that it's an
urban legend. It was too awful to contemplate.