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?

[BarryLiverstone]

By letting him plan it. You said he committed to doing it so just be available in case he has questions.

[Asker]

And if he doesn't? It won't be a dealbreaker but I'd pay attention to this, because it might show me that he doesn't care enough to take a lead even when I'm giving him all space and time to do it right? ☺

[BarryLiverstone]

If he doesn’t then that tells you how reliable he is. I get it. I am also a planner like you are. But I will step back if someone commits to planning something and judge how it turns out. If he flakes out then next time the situation comes up you will be more likely to not trust him

[BarryLiverstone]

But in reality if you want to have a serious relationship he will need to step up like this eventually right?

[Asker]

Well yes but we are both young and this is our first relationship. Last night we went out for dinner and he told me that I'm amazing and he loves me but at a totally random moment while we were eating. I'll give him some time to check this then. Not sure if i should bring it up cause we will speak tomorrow.

[BarryLiverstone]

It’s ok to talk about future plans and be excited about them. You can bring it up in a flirty way:

“I’m excited about what you are planning this weekend. But should I pack for a nice night out or pack for a clothing optional night in?”