Cross metathesis (CM) reactions of methyl oleate (MO) with cis-4-octene (OC), cis-stilbene (CS) using RuCl₂(PCy₃)(IMesH₂)(CHPh) [IMesH₂ = 1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene; Cy = cyclohexyl] afforded CM products with high MO conversion and high selectivity under high molar (OC/MO, CS/MO) ratios; CM with cis-1,4-diacetoxy-2-butene also afforded metathesis products with high MO conversion under certain conditions. The efficient CM with allyltrimethylsilane proceeded with high activity, whereas the CM with glycidyl ether, β-pinene, and vanillylidenacetone proceeded with low MO conversion.