Fast route
Do this in order
- Step 1
Give gifts during normal relationship play instead of saving the grind for the endgame.
- Step 2
Track the cumulative total yourself because the achievement counts 299 gifts, not 299 unique items.
- Step 3
Continue gifting after major relationship goals until the achievement appears; gifts across many nights count.
Prepare before you start
Check the calendar, map portraits and relationship menu before starting. Time-limited and same-night goals are easiest with every item prepared in advance.