Everyone has seen the way you've eyed Yeomen Kelly Chambers from the moment you first stepped on the Normandy in Mass Effect 2, but several flirtatious conversations seem to keep going nowhere. That's because Kelly's romance doesn't advance until the story is over, and even that depends on how well you complete the final mission.
Keeping Everyone Alive
Complete everything before starting the Reaper IFF mission. This mission is available right after the mission Collector Ship. Although this isn't specifically the point of no return in Mass Effect 2, this is the last point in which you'll have the most time to ensure the crew is ready for the final mission. Get everyone to maximum loyalty by completing their personal missions; if Shepard's crew is loyal, they're all more likely to survive. Lastly, be sure to upgrade everything you can for the ship.
With these objectives complete, start the Reaper IFF mission. When you complete this mission, a sequence of events occurs on the Normandy, leading to the most of the crew's capture, Kelly included. If you complete any additional missions at this point before passing through the Omega-4 Relay, Kelly will die. After rescuing Kelly, assign any crew member who is loyal to Shepard with the job of leading Kelly back to the ship.
"Come to My Chambers, Kelly"
If Shepard and Kelly both survive the last mission, you'll get your shot at romance following the credits. When you speak with Kelly, invite her to your quarters for a special dance routine she put together; unfortunately, you won't unlock the Paramour achievement, but Shepard also won't get in trouble from a significant other.
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