Re: First time, considering a close friend
Doing it with friends is a tough decision.
It can go good or it can go bad. Be sure you have considered all the options you can think of first....including loosing your best friend.
One suggestion, being as you said you have already talked to your friend about it would be to have this kind of a conversation between the three of you, all together, all at the same time.
Lay the cards out on the table....see if it is a win-win and that everyone is on the same page, hears and understands the rules and concerns of engagement.
I think that's the best approach if you decide to go forward with it.
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