If by "older" you mean old enough to have a non-synchro first, this
sounds normal actually

nate

   Sounds like the linkage needs adjusting.  The 'throw' on the 1st gear
linkage probably has decreased due to age & use.  Adjusting to move 1st
selector arm further in its direction of travel towards engaging should
solve the problem.  Also, put it into high momentarily before going to
1st--should stop grinding if it is not synchronized in 1st (from the
factory).  HTH, s

That sure sounds like your clutch isn't working well.  What model car
is this?
--scott

Is this a floor shift lever or a column shift?  Of course, older stick
cars do not have synchromesh on first gear, but that does not seem to be
your problem.  It sounds more like something in the shift linkage, which
is why I ask if it is a column shift lever.

If it is a floor shift the problem is likely something inside the box
itself.

A blown engine or tranny mount can cause the shifter to hit the body of
the vehicle or to bind up on the shifter boot.  I would start there.

Mike
86/00 CJ7 Laredo, 33x9.5 BFG Muds, 'glass nose to tail in '00
88 Cherokee 235 BFG AT's
Canadian Off Road Trips Photos:  Non members can still view!
Jan/06 http://www.imagestation.com/album/pictures.html?id=2115147590
(More Off Road album links at bottom of the view page)

You know, the previous owner knew about these problems, and probably
did something to temporarily mask the symptoms, with a little help from
someone.

Believe it or not, this is normal. It sometimes takes time for the
synchro mechanism to match the speeds so that you can push the stick in
all the way and mesh the dog clutch.

But what you are describing is abnormal.

Never let out the clutch until the stick is fully engaged. What happens
is that there is a little bit of travel from the point that the stick
passes thorugh the synchronizer, before the teeth actually make
contact. If the clutch starts engaging at this point, the gear will
lose its synchronization! Then when the teeth make contact, they will
grind.

If the stick won't go in, there is no point in doing anything with the
clutch. None of the additional problems that occur after you've started
letting out the clutch (like grinding) prove anything since that's
incorrect technique.

The stick won't go in because something is blocking it.

What could it be?

Maybe a blocker ring that is stuck: it intermittently won't release
when synchronization occurs, so the gear selection cannot be completed.

Maybe the synchro is okay, but the clutch doesn't fully disengage when
the pedal is all the way down, so synchronization isn't achieved?  The
pedal may need adjusting, or maybe the hydraulics or mechanical linkage
of the clutch needs to be looked into, etc.

If it's clutch-related, another possibility may be that the clutch
disk's hub does not move smoothly on the spline shaft!  The clutch
disk's hub, or the spline shaft, can rust.  You press all the way to
the floor, the clutch mechanisms do their job, the pressure plate backs
off, but the darn clutch disk doesn't slide along the shaft, away from
the flywheel, and thus takes friction from the wheel,

Could such a clutch disk problem be specific to one gear? Maybe. If the
disk is not separating from the flywheel, what will break it away, if
anything? The synchro. Higher gears have more torque in the reverse
direction from the drive shaft to the clutch, and synchros that are
typically less worn, too. If the car is moving, shifting into third
gear will apply greater torque to the clutch than first gear, because
it's a lower gear ratio in that direction. Whatever torque the synchro
manages to exert is multiplied by the gear. If you were to stop a
spinning, flat wheel with the friction of your finger, would you do it
at the edge or close to the center? Of course at the edge, where the
kinetic friction translates to more torque!

These are just wild-assed guesses.

Could it be as simple as the gear selector linkage needing adjustment?

If you shift fast, you will often feel the resistance of the blocker
ring before the gears are synced and you can connect them. But that
resistance is brief, and more or less predictable too.

Wrong question. The question is: can you go after the previous owner of
the car? Did you sign any "as is" type document?

You bought the car thinking that it had a working transmission, and
then a few days later, these problems happen. It seems that you were
ripped off!

That car has to go back to the whoever sold it to you, and you should
be looking for another car.

How very nice! Many people fancy an "older car", as do I.

Would you care to help those here to help you by telling them what
year, make and model this motor might happen to be? Or would that
information endanger some aspect of national security?