Um, is it too late to back out of this? Because, if your boyfriend isn’t really “that comfortable” around your family, maybe dragging him along on a seven day “vacation” with the whole gang (siblings’ spouses and babies included) isn’t the best idea — especially if you truly think work might be more relaxing than spending “every minute” with your boyfriend. Perhaps a better way to see how you two might survive a week of intense togetherness without fighting is to go away just the two of you before you sick your entire family on the poor guy for that amount of time. Another option may be to have your boyfriend join you and your family for only part of your vacation — say the first or last couple of days instead of the whole shebang. Seriously, a week is a long time to spend with a family that isn’t yours — and who you aren’t all that comfortable around! — along a girlfriend who thinks being at work may be more relaxing than being with you.
I know you asked for actual tips to prepare for what sounds like self-enforced torture, but my best tip for you is this: don’t do it. And if you don’t heed that tip, don’t be surprised if it blows up in your face. Traveling with a significant other can be stressful. Traveling with a significant other plus your entire family for a whole week when you know your significant other doesn’t feel comfortable around your peeps sounds like a real recipe for disaster. Why put yourself — and him — through that if you don’t have to? But if you do, please be sure to make plenty of time for just the two of you — a dinner or two out, romantic walks along the beach, etc. And if that really doesn’t appeal to you, then again, I urge you to reconsider dragging your boyfriend with you this time. Maybe being the only single sibling left in your family has been a lonesome feeling, but don’t let that be the reason you put him through a week of discomfort.
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