Lock Up Your Sons ... And Mothers. Cupcake and Pop are dating again.

You know when your friend comes to you for relationship advice, she'll pour out every tedious detail of her break-up, then you try to respond with compassionate, rational advice that she promptly disregards? Fun, right? Now imagine going through this scenario with your father.

My father and his long-time girlfriend recently broke up. It kind of came out of nowhere, and there was no real good reason for it, it just happened. I spent a lot of time talking about it with my father, giving him advice, including some of my own precious tips like, "Put a Post-It note on the phone that says 'don't call her', then everytime you're tempted and you pick up the phone, you'll see the note". It didn't work. Whether or not the advice I gave him was sound, we'll never know since he seemed unable to follow it anyways. It's been a month now, and the man is ready to date again.

My father's plan to re-enter the scene after an almost eight year absence is to put out the word that he's looking. He wants me to come up with some candidates, but, believe it or not, I don't actually know that many middle-aged single women living in Rhode Island. I've tried to lecture him about rebound relationships and tell him that maybe he should just take some time to enjoy being single; he isn't buying it. At all. Although he's not really looking to jump into another relationship, he wants someone to go out with. He calls me a lot, says that weekends are the hardest because the hours just kind of stretch out, with no one to spend them with. I tell him, welcome to my world. I sympathize with him, I do, but I tell him that he just described every weekend of my adult life and that he has to make a life for himself independent of another person. He tells me to cut the Dr. Phil crap. Okay, I concede that its easier for me because I do have a lot of single friends in the city, but I swear if he keeps making single life out to be a death sentence, I'm going to throw myself under a B67 bus.

To try to help my father out, I went on Match.com to try to look for single women in his area. As soon as the results came up and I started clicking on profiles I got hit by a wave of nausea. I was at work, and I literally thought I was going to have to put my head between my knees and take some deep breaths. As one friend put it, "Why are you are Yenta-ing out your father?!" I don't know. I'm just trying to help.

The problem I soon encountered was that every Match.com profile is basically the same. The bad ones drone on about a knight in shining armor, or blather on about their cats. Barf. The good ones say that they enjoy traveling to exotic places, reading novels, hiking, staying active, going to the beach and the occasional museum. Okay, this is just not going to work. My father does not like to travel. He has a comfort zone that is about 20 minutes driving time in either direction from his house and he doesn't really care to venture outside of it. You might be able to get him on a cruise or trip to Florida, but he also hates flying. His enjoyment of nature is limited to sitting on a park bench and smoking a cigar. Reading? Rarely. Museums? Never. Hiking? You're kidding, right?

I realized that I could solve a few problems if I just married my father myself, but I came to see, with the help of my roommates, that this is not really a viable option. And yet, I can't help thinking that if I had been born maybe two or three decades before, this is what my life would have resembled. My mother died when I was sixteen, and in a different age, I would have been expected to stay home, take care of my father, then get a job to contribute to the household income. I couldn't have even thought about dating or marriage unless I was ready to move the Old Man in with us. I think about people in my family, of different generations, who gave up their lives like this to take care of their aging parents. Since I thought of it that way, every day of my fabulously independent life, every day that I manage to navigate this city and my job and have a social life seems like a minor miracle and an incredible opportunity that I am just not going to take for granted anymore.

I was out with my friend LaHipster last night, who is wonderfully insane. Over ice cream at Maggie Moo's (cake batter with a Butterfinger mix-in, if you must know), we talked about dating. I told her I was on an indefinite dating hiatus. LaHipster likes to date older men, and she loves physical deformities. Acne scars? Great. Snaggle tooth? Yummy. Missing a limb? Bring it on. But the last guy, like so many others, had just disappeared after a promising start. She said she just couldn't do it anymore. She said, "Do you ever feel like you just keep putting yourself out there and putting yourself out there for ... nothing?" I did, but I wanted to take a hopeful tack. I likened it to that post-college unemployment phase, where you just keep sending out resumes, keep going on interviews until you don't think you can do it anymore, you're certain that one more rejection might actually kill you (and I'd like to point out that I applied for way more jobs (approx. 400) than dated guys). You just don't think you can take anymore rejection, but you have to keep. doing. it. Then something hits. And as I'm sitting here at my pretty sweet job, I can't help but think that maybe it's time to starting dating again. What the hell? Only 380 guys to go...