Bad dates are good material.

During the date, we got in a huge argument over whether Tom Cruise was irresponsible to say that women with postpartum depression should suck it up and take vitamins instead of medication. My date told me I was over-thinking it because women fake postpartum depression all the time. I told him that I felt sorry for his future wife, slapped money down for my coffee, and left. The next day he called to say he’d had a great time.

We made plans to go out, and I knew from a previous conversation with him that he had an ex-girlfriend who was pregnant with his child. When we met up, we had a good time talking and drinking all night–and then he mentioned that his child was born that very night and he had left the hospital to come meet me.

We met on the dance floor, swing dancing to be exact. He was fawning all over me, flirting shamelessly. By the way, I’m 56 and he’s 60. We go out for a date and had fun, were really comfortable together, and got  intimate–but then he dropped a bomb, saying, “You should use some of your inheritance and treat yourself to breast augmentation surgery.” WHAT? I’m perfectly happy just the way I am (and FYI, I wear a 32 C), but he told me he “just couldn’t handle it.”

When setting up our date, he repeated several times, “I’m going to pay for all this. I want it to be a REAL date.” I pick him up and we head to a Thai restaurant he picked in a seedy part of town. There are absolutely NO customers except for us–strange for 7:30pm on a Friday night. I have no idea why we drove all the way out here, seeing as there are a bunch of Thai restaurants closer in, but I soon realize why: He wants to have an art show in the gallery below the restaurant and  didn’t want to take the long bus ride to check it out, so he figured he’d just tack the visit onto date. As we look at the menu he comments about how expensive everything is–he orders a water and asks if we can share something (I again offer to go dutch but he’s still adamant about paying). We get our food and when the server doesn’t bring me a plate, I ask for one, to which my date says, “Let’s just use one.” I thought it was to be romantic, but it was actually so he could eat almost the entire thing himself. We head to the movies where he complains about the price of tickets, the price of popcorn, the price of soda…and pays for the whole thing with a gift card he got for his birthday a few years ago! I gladly dropped him off after the movie and didn’t return his text the next day that said, “Next time it’s your turn.”

We had a good (not great, but fine) time over dinner–he was awkward, but I mostly found it endearing. The next day, I got a text from him that said, “Are we exclusive?” I ignored it, not sure if it was a joke or he was nuts. He texted again: “I need to know–have another date tonight and not sure if I should cancel.” Kind of cute that he wanted to do right by me, but a guy who thinks a one-hour dinner makes a relationship is probably just too clueless for me.

When we meet up to go to a hockey game, he smells like booze and reveals he has chugged a six pack because “the beers in the arena are so expensive.” He is drunk and won’t shut up. At the game, I am thirsty and mention I’d like a beer. [crickets] Since he doesn’t offer, I say I’ll get myself one and him one ($8 a pop, he has a point) and he says “Oh yeah, that’d be great!” He gets drunker and won’t shut up. I learn intimate details of ex-girlfriends and his grandmother’s incontinence. He also regales me with a tale of a work event where he got “a bit tipsy” and was told to leave, because he may have a drinking problem. He informs me, in breath laden with Bud Light, “I don’t have a friggin’ problem. I’m a friggin’ young guy. I just friggin’ like to have friggin’ fun.”

We met at the library of all places, and had a really intellectual talk about our favorite books. We exchanged numbers, and I called him a few days later to see if he wanted to meet up again. When I asked what he was doing, he said, “Not much–just watching some porn.” I thought it was a joke until he asked if I wanted to come over and watch with him.

We were supposed to meet at a cute restaurant in my neighborhood at 7:30 that night. I went out to walk my dog, leaving just enough time to shower, do my hair and makeup, and change into a dress and heels when I got back. But when I got home, I realized I’d left my keys inside and locked myself out. I called a friend with the spare, but she couldn’t be there for an hour. Rather than stand him up, I texted him with the situation and–to my total embarrassment–he wanted to come meet me. He showed up at my front steps all ready for our date, and I was in a ratty T-shirt and jean shorts. He handled it well, but it wasn’t exactly the first impression I wanted to make.

Before he asked me out, we only talked briefly (about how I had just graduated from college. He looked like he was in his late 20s, and said he was currently a student after taking some time off). For our date, he took me to a bar to hear his favorite band. It turned out that it was his father’s band. I then met his father (awkward), who made a comment about how he wanted to take us out to get to know his son’s girl (um, this was a first date). Then, we sat down at a table and were ordering drinks, and started comparing driver’s license photos… and I saw that my date was 38! He knew full well that I was 22! Apparently, he was okay with that, but I most definitely was not.

When I picked him up, he’d just gotten a hamburger and chips and proceeded to eat them in my car. (I thought we were going for a meal, so I hadn’t eaten.) Then he asked if we could make a quick stop, so I followed his directions, and we ended up at his pot dealer’s house. I sat there for an hour watching them smoke before I stood up and announced that I was leaving. He asked for a ride home and I said okay. Before he got out of the car, he asked, “Can I touch you ‘down there’?” Needless to say, the answer was no.