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That question wobbles a bit depending on whom your actually talking about.
If I'm your ally you can freely move through my square but can't stop in it as long as I'm still conscious.
If I happen to be your bitter foe however I will resolutely prevent you from entering my square or moving through it unless you manage to perform either some form of combat maneuver as you suggested or you succeed in an acrobatics check versus my CMD +5 (EDIT: Bearded Ben got it more correct!) You can't stand in my square at all unless I happen to be laying on the floor unconscious.
Of course there may be times when this isn't always the case. Special rules, abilities and the like come up when we're both not just generic medium sized humanoids, but those should be clearly labeled.

asthyril |

i would think the only way to stand in a square of the same sized opponent as you, is to make some kind of combat maneuver to get them out of that square. bull rush, re-position, a few magic ways i can think of (forced teleport or spells that bull rush)
i have often wondered what happens when someone falls into an enemy square though, by the rules. if you jump off a wall into an enemies' square, what happens?

Darksol the Painbringer |

Well Douglas, RAW you can't go into the space of an enemy's square unless there is a specific ability that allows you to do so (and comes with limitations; etherealness is a prime example). RAI, I believe that what you are trying to accomplish (assuming the guidelines you presented) is quite doable, but through an unorthodox measure.
I cannot step into the square of an enemy who is standing and conscious (you used to have to do this with grappling, but that was changed), but if either of those conditions aren't met, it is possible to do so. An unconscious enemy is a no-brainer, but what about an enemy who is on his/her back, or prone? Should be fairly easy.
Assuming you both have 5' reach, you move into melee range and want a means to force the target to become prone. Since they are medium, you can use the Trip maneuver. On a successful Trip maneuver, the target becomes prone; the best part about this is that if you use a Standard Action to Trip, you still have a Movement Action to either move into or past that square (but beware that if it's not just a 5-Foot Step, this movement will still provoke an Attack of Opportunity from the prone target, though they will have a -4 penalty to the swing).
If all you need to do is utilize a 5-Foot Step to stand in that enemy's square, you can also go ahead and utilize a Full Attack Action for a slew of Trip Attempts against the target until you get a success in (and any other attack rolls you have remaining can be used to beat the target down with those bonuses to hit).
I hope this helps!
(P.S. @ Asthyril: Assuming a reach of 5 feet, the PC will pass through a 10 foot threshold, all of which that creature threatens, meaning that when the PC makes the attack [or whatever action they are attempting], the creature will get to make an attack of opportunity after the PC's attack is resolved [since they can make their attack once the creature is in range, which occurs before the PC moves over 10 feet].)

Rynjin |

i would think the only way to stand in a square of the same sized opponent as you, is to make some kind of combat maneuver to get them out of that square. bull rush, re-position, a few magic ways i can think of (forced teleport or spells that bull rush)
i have often wondered what happens when someone falls into an enemy square though, by the rules. if you jump off a wall into an enemies' square, what happens?
Pretty sure you land on them and can take an attack, but you kinda roll off and land in an adjacent square.

Grick |
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i have often wondered what happens when someone falls into an enemy square though, by the rules. if you jump off a wall into an enemies' square, what happens?
Accidentally Ending Movement in an Illegal Space: "Sometimes a character ends its movement while moving through a space where it's not allowed to stop. When that happens, put your miniature in the last legal position you occupied, or the closest legal position, if there's a legal position that's closer."
Since the square above the enemy isn't a legal position to stay (unless you can fly/hover/etc) you'll get moved to an adjacent square.

Troubleshooter |

Well Douglas, RAW you can't go into the space of an enemy's square unless there is a specific ability that allows you to do so (and comes with limitations; etherealness is a prime example). RAI, I believe that what you are trying to accomplish (assuming the guidelines you presented) is quite doable, but through an unorthodox measure.
I cannot step into the square of an enemy who is standing and conscious (you used to have to do this with grappling, but that was changed), but if either of those conditions aren't met, it is possible to do so. An unconscious enemy is a no-brainer, but what about an enemy who is on his/her back, or prone? Should be fairly easy.
Assuming you both have 5' reach, you move into melee range and want a means to force the target to become prone. Since they are medium, you can use the Trip maneuver. On a successful Trip maneuver, the target becomes prone; the best part about this is that if you use a Standard Action to Trip, you still have a Movement Action to either move into or past that square (but beware that if it's not just a 5-Foot Step, this movement will still provoke an Attack of Opportunity from the prone target, though they will have a -4 penalty to the swing).
If all you need to do is utilize a 5-Foot Step to stand in that enemy's square, you can also go ahead and utilize a Full Attack Action for a slew of Trip Attempts against the target until you get a success in (and any other attack rolls you have remaining can be used to beat the target down with those bonuses to hit).
I hope this helps!
(P.S. @ Asthyril: Assuming a reach of 5 feet, the PC will pass through a 10 foot threshold, all of which that creature threatens, meaning that when the PC makes the attack [or whatever action they are attempting], the creature will get to make an attack of opportunity after the PC's attack is resolved [since they can make their attack once the creature is in range, which occurs before the PC moves over 10 feet].)
As long as you realize this is an adjudication. By RAW, you can't occupy an enemy's square just because they are Prone.

Troubleshooter |

Yes. RAW states that you cannot generally occupy a square of another creature, then lists specific exceptions that allow you to do so. Tiny and smaller creatures are one such listed exception.
Interestingly, it doesn't actually say they can occupy the square -- just enter, and move through. A very strict reading may cause a DM to assume that such a creature would have to enter a square, perform their attack, then get shunted to their last legal space after their turn concludes. Though I'm not sure that is the intention.