Can Jesus sympathize with what we are going through?
Yes. Jesus, our great High Priest who passed into the heavens, is not a high priest who cannot be touched. He can be touched with the feeling of our infirmities, and He remains constantly aware of our moment-by-moment existence, so He sympathizes with what believers go through.
Les teaches from Hebrews 4:14-16 that as believers we face temptation every day and will never leave it until we leave this life, but we have promises to hang on to. He points out that Jesus, the Son of God, has passed into the heavens as our great High Priest, fulfilling the priesthood of Melchizedek, and is constantly aware of our moment-by-moment existence. Les emphasizes the positive reading of verse 15: we do not have a high priest who cannot be touched; we have a high priest who can be touched with the feeling of our infirmities.
For we have not an high priest which cannot be touched with the feeling of our infirmities; but was in all points tempted like as we are, yet without sin.