In the Company of Men (1997)

Chad, a cold-hearted, sexist pig, has recently been dumped by his girlfriend Suzanne. His friend, Howie, is also having relationship troubles. Chad then comes up with a plan to satisfy their hate towards women; find a vulnerable woman with low self-esteem, date her for six weeks, and then dump her like she's never been dumped before. Howie agrees to the plan, though very reluctantly. Chad finds a worthy target in Christine, a beautiful, deaf secretary with a heart of gold. While Chad coldly slimes his way into her heart, Howie finds himself honestly falling in love with her, and finds himself changing his mind about the plan.

anonymous spoiler