[mushaboom]

I've been asked to explain whether dimethyl maleate or dimethyl fumarate is more stable thermodynamically. Dimethyl maleate is more polar, giving it a higher boiling point while dimethyl fumarate is the trans isomer so it "stacks better" and also has less steric interaction than DMM. Given these two observations, I'm not sure which is the correct answer.

[orgopete]

I believe the question is asking about the INTRAmolecular forces, not the INTERmolecular forces. Melting and boiling points tell you about intermolecular forces.

[zsinger]

Orgopete is most certainly correct.  We can only study chemistry in two fundamental ways: thermodynamically and kinetically.  This is a thermodynamics argument which, as Pete pointed out, is due to the forces between the individual atoms of the molecule and not the molecule in relation to others.  I hope this furthers your understand.
          -Zack

[mushaboom]

Got it; thank you both!