Let me add, as an aside, that some would warn that you make those plans with someone of the same gender, lest you end up creating confusion or giving false impressions with your friend. Personally, sometimes I found that to be true, but there were other relationships in which a member of the opposite sex and I had clear discussions about our friendship and expectations, and so understood we were not interested in dating. In any case, however you choose to handle it, I encourage you now to identify some of those times that might feel particularly lonely or painful, such as sitting alone at a Christmas Eve candlelight service, and begin making arrangements to avoid unnecessary hardship.
The other suggestion I would like to offer is along the same lines, but with a different twist. If you choose to not put yourself in loneliness producing situations unnecessarily, then consider going one step further. Instead of focusing solely upon how YOU will feel in that time, is it possible you could find another person or persons who have needs that you could meet by using that time to minister or care for THEM? In other words, look out for somebody ELSE’S best interest, needs, or feelings. Be the one who helps somebody else conquer their loneliness by offering your friendship. I can guarantee you our world is full of people who long to know that somebody cares. Some of them live in nursing homes. Others work in sheltered workshops. Still others are just walking out of the divorce court themselves. And others have just left a loved one in a cemetery. YOU could be the key that could make all the difference in another person. If you begin to look for people who need a friend, and for ways to make that difference. You may find your holidays transformed into something more special than you imagine.
Oh, and by the way, a wise friend reminded me during my lonely days that though I might feel lonely, I was never truly alone. Because we have a God who promises to never forsake us. Don’t forget to include Him in your holiday plans, too!
TL:dr Holidays can be lonely, but less so if you plan ahead and involve yourself with others