At start, when you reach to Michelle's house, Roman phones you saying he is getting beatings from Darden and his friends. So, what you guys chose? Did you go for your love and let Roman suffer? Or did you helped you cousin and depressed Michelle?
I went for Bleed Out. Just because I know how Roman is.
On my first playthrough of GTA IV I went for First Date only because Roman phoned me when I was already in front of Michelle's house, so I thought, "I can't really be bothered to drive all the way over to Roman not whilst I'm here now."
Though on my other playthroughs of IV I've chosen Bleed Out only because I tend to try and complete all of the missions for one contact/mission giver before I move on to someone else.
Well, after doing it many times, I went to Bleed Out because I didn't want to pick up Roman in the hospital and then do the mission, also, you will be like only one hour late, and Michelle will be waiting for you.
Well if you choose First Date then you get a text from Roman and you do Bleed Out anyway, whereas I don't think you can do First Date if you do Bleed Out first, although I may be mistaken. You relationship score with Michelle is hurt if you choose Bleed Out first, that's for sure.
I don't leave anyone hanging: After Michelle calls me, I put my phone onto sleep mode so that Roman can't call me and give me his mission. After that "First Date" ends, I get the normal mission-initiating phone call from Roman about how he needs my help, and then help him. So Roman doesn't get beaten up, and I don't have to cancel my plans with Michelle.
If I couldn't do that, then I'd just cancel the date with Michelle and do it later, because you can't cancel saving your cousin from loansharks.