1) Ch. 37, v. 35: "Va'yimo'ein l'hisnacheim" And he refused to console himself Rashi explains that although Hashem set into a person's psyche to forget the sorrow of the death of a loved one after the passing of a year (gemara P'sochim 54b), there is no consolation when the assumed deceased is actually alive (maseches Sofrim ch. #21). If so, why didn't Yaakov realize that Yoseif must still be alive?
2) Ch. 37, v. 36: "V'haM'donim mochru oso el Mitzroyim l'Photifar" And the M'donim sold him to Mitzrayim to Potifar A new name appears on the scene, M'donim. Targum Onkelos, mosaf Rashi, and some Baa'lei Tosfos, say that they are the Midyonim of verse 28. They offer no explanation for the change from Midyonim to M'donim. However, Targum Yonoson ben Uziel does not translate as Targum Onkelos, "uMidyono'ei," but rather, "uM'dono'ei," seeming to indicate that he is of the opinion that they are two nations. Similarly, some Baa'lei Tosfos say that there are two distinct groups, Midyonim and M'donim, descended from Avrohom's offspring, as we find, "Va'tei'led lo v'es M'don v'es Midyon." The Rashbam says that M'don and Yishmoeil are one nation. He does not explain why the Torah calls them Yish'm'eilim in verse 28 and M'donim here.
According to the commentators who say they are one and the same, why indeed does the Torah give them two names?
3) Ch. 38, v. 14: "Va'teishev b'fesach einayim" And she sat at a road junction This is Rashi's interpretation. The reason that a road junction is called "pesach einayim" is because one has to open his eyes, i.e. pay special attention at a junction, so that he continues his trip on the proper path (Rabbeinu Menachem and Pirush al Targum Yonoson ben Uziel). If this is so, why in verse 21 do we only have "vo'einayim al ha'derech," without "pesach"?
4) Ch. 38, v. 23: "Pen ni'h'yeh lovuz" Lest we will be a mockery Why a mockery? It would seem that a term along the lines of dishonestly, not keeping one's word, or the like would be more fitting.
5) Ch. 38, v. 25: "V'hee sholchoh el chomihoh" And she sent to her father-in-law Rashi (gemara Brochos 43b) says that Tomor did not simply say that Yehudoh impregnated her. Rather she only sent his payment, saying, "The man to whom these items belong is responsible for my pregnancy. If he admits it fine, and if not, let them burn me rather than my embarrassing him." From this we derive that it is preferable for a person to throw himself into a fiery cauldron rather than embarrassing his fellow man.
The Baal Haturim and Rabbi Yehudoh Chosid say that Yehudoh's words of the previous verse, "Hotziuhoh v'siso'reif," do not mean that she was to be burned to death, but rather, that a mark be made on her face with a burning brand, as a constant sign to her sin. If so, what is the proof that it is preferable to be burned to death, as that wasn't going to be her punishment? As well, how do we derive that it is preferable to "throw oneself" as she was not about to do this to herself, but rather, it would be done by others?