The Loneliest Time of Year

It’s been a while, but I’m back.

I took some time off for personal discovery, adventure, and soul finding. I found a lot of what I was looking for, but not everything. Over the summer I had hoped to find Prince Charming. I wanted someone special to spend my time with, someone to have romantic escapades with that most dream about. I didn’t find him, but I did make some great new friends that I wouldn’t trade for the world.

Now I’m back in my beloved City of Roses, and after being gone, I’m even more in love with Portland.

The winter can be a dreaded time for most, but it still has some great moments. The holiday season is a wonderful time filled with kindness and magic. Downtown Portland is lined with trees wrapped in white lights, Pioneer Square is buzzing with holiday shoppers, and the mighty Christmas tree stands tall.

The real downside of winter in Portland is when you have to spend it alone. If you don’t have someone locked in before Thanksgiving you’re screwed. Dating is increasingly hard after the summer weather ends. With fewer options for a fun date, it takes longer to get to know someone. Once you get near Thanksgiving people are too busy with holiday preparations and plans that they don’t have time for a first or second date with someone they barely know. So unless you manage to fall into a relationship within a week, your chances of spending time with a special someone continue to dwindle as the date gets nearer to Christmas and New Years Eve.

Then you can look forward to spending Valentine’s Day alone, unless you take full advantage of January. This small window of opportunity is the best chance of snagging a date for February 14th.

There are some exceptions to the dating game. Some people have no problem finding a partner for the holidays, and others have no guilt about dumping their current lover around the holidays (sooooo wrong), but for the average person with a life and responsibilities, winter can be just as lonely and dry as a desert in the summer.

As I took a power nap on my lunch break today, I reclined in my car listening to the sound of the rain hitting the windshield. I kept hearing people’s voices saying how some day I will find the right person, and I wondered if that’s true then how long will I have to wait? If he’s out there, then where is he right now? If someday we’re together talking about our youth and how we wished we had met earlier instead of wasting so much time then how can we speed up the process?

If everything happens for a reason, then what’s the reason for me being single for so long? Not to sound conceited but everyone else says I’m a catch, and my standards aren’t that high. I’m excellent on dates, and I have motivation and goals for my life. I should have been snatched up a long time ago. In movies and on TV I’m the one people fight over. In real life however, it seems like no one wants to give me the time of day.

As the cold and bitterness seeps into my gloomy attitude this winter, I’ll try to stay warm at the thought that some day I will have him to hold. Until then I can only hope that one of the frogs I kiss along the way with be worth the effort.

A question for anyone who might be reading: How do you keep warm during the winter? If you have any great Portland winter date ideas, let me know @ portlandpridecityboi@gmail.com

You know you love it,
xoxo,
~ city boi