Weekend get away- how to approach this?

Anonymous
I am more of type A personality and my boyfriend is type B (laid back and chilled, not much organized) but we both have great sense of humour and learn to balance this difference. At the moment we are facing something I believe it's an opportunity to grow closer and bond and learn to trust each other more. He is going away next week with his buddies (I met them and they also invited me) but I'm working the whole week and cannot join him. He was kind of upset about it so it ended up in a discussion that I'm working a lot and don't take paid leaves. I sensed that he got frustrated and so I proposed to go this weekend away the both of us if he's free. He said this is not a bad idea and he will check some deals for a weekend away. I asked him if he can check it cause i won't have time to do it. He committed to do it but the thing is, I am the one initiating and scheduling our dates. This time I really want to give him the chance to organize something for us. This is really our only "trouble" his time management and lack of initiative even when it comes to calling each other. I love him because of and despite this trait. He mentioned many times that I am the responsible one and he likes that I take the pressure off him. He started showing me his frustration that we hang out less than before cause of my job but hasn't step up to initiate more knowing that I've got limited time than before. For this weekend, don't want to push it though cause I want to show him that I trust him to schedule a date or mini trip for us instead of bossing him around and him following my lead. How can I do that?
Weekend get away- how to approach this?
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