1. When I was 29, I dated a guy named Louis, for a few months. I liked him. He was nice and cute and sexy and had a real job (he was a lawyer, not an artist.) We saw each other about once or twice a week. He wasn’t my boyfriend; we were just dating.

One day, Louis came down with a terrible cold and I decided to send chicken soup to his work. But there was a $25 minimum delivery so I ended up sending him 2 orders of matzo ball soup, two orders of French fries and a slice of chocolate mousse cake, so I could get to the minimum.

When he called to thank me, he kept saying, “Wow. This is a lot of food. I mean, it’s SO MUCH food.” His thank you was awkward. I felt shamed that I’d sent him enough French fries for 5 people. The enormous food delivery changed everything, I think, because we broke up on our next date, like this:

Me: So…. What do you think about what’s happening with us? (Inspired by the unplesant thank you for the gallon of soup.)

Louis: Yeah, I don’t think this is really working out. Wow, thank you for bringing this up. If you didn’t bring this up, I never would have. I mean, we probably would have gotten married before I would have ever brought this up. Whew, this is a relief.

So… Can I count that as a marriage proposal?

2. Simon and I had been on 2 dates. He was a 35 year old struggling jazz musician and cute. We met on line.

I got a voice mail from him saying, “I’m sick. Could you bring me soup?”

I barely knew the guy, but I decided I’d bring him soup – I mean, why not; maybe he would be my boyfriend someday. Maybe me saying yes would progress this relationship.

When I called to tell him I would bring his soup, he said, “I also need: cough drops, Kleenex, fruit, juice and Popsicles.”

I was quiet for a moment. Then I said, “so, you need me to go shopping for you?”

“Huh? Oh and Day quill,” he said.

He never actually admitted that he was asking me to shop for him and yet, I did. I showed up at his germy place with 2 bags of groceries, for this guy I’d met twice before.

“Wow, this is great,” he said, riffling through the bag of things he’d ordered me to get and NOT actually ever saying the words thank you.

“Can I…. Pay you?” he asked, as if he was sure I’d slap his hand and shout your money’s no good here!

His groceries had cost me about $60 and since we’d gone dutch on our 2 dates, it’s not like I owed him. But how the hell could I say Yes, please pay me $60?
I couldn’t.

“It’s OK,” I told him.

“Wow! Great!” He said, again not really saying thank you. “Here, take some chocolates.” He reached in a drawer and gave me a handful of those Ferrero Rocher chocolate balls that they sell for cheap at fine drug stores.

“Do you want to watch a movie with me?” He asked, with a stuffy nose so he said “boovie” instead of movie.

I’d driven about 30 minutes to get to his house, not to mention the travel time and shop time.

“OK,” I said and I sat on his couch that smelled of sick and watched a bit of “Shaun of the Dead,” while he utilized all the booty I had brought him. I wondered if this was all a ploy to get free stuff. I watched the move for about 15 minutes thinking, how soon can I go? To this day, that movie makes me feel dirty.

When he was well, we had a few more dates, but I never got over this whole weird cold-shopping incident. When I ended things with him, he got mad and called me a moron.

3. While I was trying to get pregnant, I had a date with Ian and I thought I might be pregnant.

“Let’s meet for margaritas,” Ian said. As I’ve mentioned before, I like to let the guy plan a date; it gives me good insight to his character.

Ian ordered his margarita and I, a geek on a first date who thought she might be pregnant, ordered a virgin.

It took a while for the bartender to truly grasp that I wanted lemon lime mix blended with ice, as I avoided Ian’s eyes.

When I finally looked at Ian, he asked, “you don’t drink?”

“Um, not right now,” I mumbled. I hadn’t really thought this through. I sounded more cryptic than intended, though, it was a pretty major conversation for a first date. I should have just said, I’m taking antibiotics. That’s a good one.

I sipped my disgusting margarita mix as we chatted. Even though it was a hot, summer night, my drink was not refreshing. The conversation was.

Ian was really nice and smart. We talked about things that were actually interesting to me. But, after a few minutes, Ian pulled out a huge wad of Kleenex and blew his nose in a very productive way.

I must have given him a look because he said, sweetly, “it’s just a summer cold.”

For the rest of the night, through our conversations about work and art, all I wanted to do was talk about the difference between a cold and a summer old. Did that mean it wasn’t catchy? Did that mean it is actually cured by tequila? What the hell was a summer cold and why was it ok to be on a first date with one?

The nose blowing continued right up to the moment he tried to kiss maybe pregnant me. It was just all too much. I didn’t want to get sick and it was too soon to tell him that I was trying to be a single mom and this might have been my first virgin cocktail with child.

As he kissed me, I tried to keep my mouth closed to minimize the germ contact. He seemed pretty into it. I was completely freaked out and I made an awkward exit.

I wasn’t pregnant at this point, by the way.

A few years later, I crossed paths with Ian again and we met for a cup of coffee together. I brought Spenser. Here’s the crazy part; we never talked about me being a single mom. I don’t know if he thought I was in a relationship or not. Maybe it wasn’t really a date, but whatever it was, I don’t think he had fun. I barely sat with him, because Spenser was running around non stop and I complained about my drink (that he bought me.) After maybe 15 minutes, he said, “Well, I guess I should let you go.” Which meant he wanted to go.

I recently had the best date of my life and we were both getting over colds. We split a burger and fries and he didn’t even offer to pay.