Victories But Different Endings

I'm sure all of you have played one or more, or just HEARD games with open-ended gameplay, in other words, multiple endings. Usually it would be... Win, and get a certain result and then another also win, but a different result. Both are quite on par on worthwhile. Say you're a conquerer that has the ULTIMATE army. Conquering America, you will get the power of technology and conquering Iraq will get you oil. Either way, it's a good win, right? No losses whatsoever, discounting minimal foot soilder casualties la. Alright, straight to the point....

Scenario: Girl mentions that she likes another dude but I just freakin' gave her some V-day stuff. Should I go for it or screw it?

Action: Go for it!
Rewards: A relationship (Okay, might be a curse for some, but heck, willing to check this out)
Losses: Nothing much, except some alone time and attention that might be better used for other things. And awkward moments perhaps.

OR

Action: Screw it!
Rewards: More alone time and attention for other things and being SINGLE, and no awkward moments especially when things go real south. AND might have a better chance at another potential candidate!
Losses: 100 bucks.

Hmmm... Wow, Seems like a real doozie. I win in both scenarios and both prizes seem worthwhile. Losses are not too big in both, too. Seriously I have no idea what to do. And if you have no good advice (ie: Eating shorts) then dig deep down and think again, or just forget it. Damn man... I wonder who said life was simple? Must've been that Tokyo Drift dude. Peace out y'all.