5 Ways to Comfort a Heartbroken Guy Friend and Get Him Interested in You

5. Take advantage of the situation and confess your crush.

You could also surprise a heartbroken guy friend by confessing your crush. He might even say yes if you ask him out. “When men feel vulnerable, we are more likely to go with the flow,” a guy in his 20s explained. If your guy friend agrees to go out with you, plan your first date before he calms down. It’s essential that you take the lead at the beginning of the dating phase.