I'm still new at my job...going on three months.

I have already requested two days off. I had requested November 20th off to celebrate my Thanksgiving and I have requested December 6th off to welcome my brother home from the military. I requested both of them off a month in advance.

I need to request January 1st-3rd off because I will be going out of town. I've planned these dates out months in advance and I will offer to work the following two days after (the 4th-5th is my assigned days off) but I am concerned for two reasons, first, because I have already requested two days off, and second, because on my Friday my boss and I spoke about switching from PT Front Desk/Housekeeping to FT Housekeeping until they find a new housekeeper to replace me and I feel it is bad timing to switch my schedule around only to ask for more time off when I am so new.

But my plans are very important to me because my best friends are also requesting time off to go out of town with me. It would be awful to have to cancel plans after months of planning it out, but at the same time I don't want to seem like a flaky employee. At least if I do request the time off I will offer to work extra days.

What should I do? After changing my schedule around I feel bad to request more time off, even if it's only three days off with the offer of working extra days, but at the same time I've been planning on going away since August and my best friends are involved as well and I'd be letting them down if I don't request the time off, and I need to request it off as soon as possible. If I request it now, then I have a whole month's notice, but I also feel it's bad timing.