Perhaps approach him and explain it ' s just a temporary covering of expenses , and let him know when you ' ll pay him back for it . That might make it harder for him to give you a run around . I would hold off on telling him you don ' t plan to have a rehearsal dinner for now , because he might be offended by that . But approach him more in a We need $ X by X date in order to secure our dream venue . We can either pay you fully by X date , or can pay you back in X amount of installments if you prefer . We really appreciate you ' re ability to help us out while we transition between jobs blah blah blah butter him up . I ' m sure plenty will say something about don ' t count on money until you have it , and there is truth for sure . Use this experience to know not to count on anything from him despite what he says . Also , try and contact the venue and see if you can do a partial deposit split up . If your date isn ' t super popular , they might be willing to do that too .