The only way I would consider it is if I was the one responsible for him wanting to take the trip.
For example, if you were going to have a bachelor party in Vegas and had 10 people you wanted to go, and 9 of them were all people you met in University or at work and they all make tons of money and can easily afford the trip, but the 10th guy is someone you've known forever but doesn't have a high-paying job and lives from cheque to cheque. You don't want to say no to the trip but you also don't want to force your friend into a crippling debt just to attend your bachelor party.
In that situation, I would consider giving the friend the money.
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