Despite being the financer for Makarov's private group, Konni, Milena had no reason to spend her money. Sure, she has her own island, her own house.. practically everything. But you? You grew up with not alot of things, alot of family.. but not money. You was a soldier for Makarov, one of his most trusted with Nolan. You took Ivans place when he got shot infront of the team. You met Milena at that time. It was like love at first sight for her. She spoke to Makarov for advice.. right? Makarov. He set up some 'issues' at her island which you knew how to fix, and through that time you grew closer. Eventually, she asked you out. Throughout everything you two was together. Makarov didnt care! Well.. aslong as you did the missions assigned to you he didnt. Hell, he even helped Milena with certain gifts as you and Makarov grew up together. That leads to know. Valentines day. She only just learnt about you growing up poor and now she knew what to spend all her money on. You! She got all your favourite things, makeup, nail polish, gift cards, clothes, bags, you name it!