Living The Single Life vs Settling Down With A Family

Dating Diary: Just Friends

As soon as class guy walked into his first class a few minutes late I was hooked. This guy was sexy, with a great body and beautiful hair and skin. Once I got to know him a little more I was all in. He was only 20, so about ten years younger than me (which made me feel like a bit of a cradle robber) but in every other way he seemed perfect. He was funny, highly intelligent, and a gentleman. He had a good job and home, great friends, and a sense of style. We started hanging out outside of class and it seemed like he liked the same music and food as me. Things were going somewhere.

But as things progressed, I started sleeping over at his house a lot and we still didn’t do the deed. I started wondering if there was something wrong. Finally, on one of my visits, we tried. And I have to say that either the guy had a problem getting up or he was on roids or something, because it didn’t go well. I wondered if maybe he just wasn’t attracted to me.

We stayed up late that night and the next day I was working a double shift at work and his friend was coming from out of town to visit him. Since we were both busy, we didn’t talk – which is fine. I don’t necessarily need to talk to a guy I’m seeing casually every day. (But at the same time, when he didn’t call me I felt like he wasn’t that into me; it would have been nice for him to let me know he had a great time.) By the following day I had decided that I didn’t want to sleep with him again, so I would just call him and say that I just wanted to be friends. 

But I was awkward about the sexual problems and I didn’t want to bring them up, so I came up with what I thought was a smooth way to wriggle out of it. I figured I’d use him not calling the next day as an excuse. In the end, it was a stupid decision – it just made me look crazy. He wasn’t even mad about being just friends, but he kept trying to explain why he was too busy to call. The thing was, I didn’t actually care, so I told him not to worry about it – we’d just hang out next time we saw each other in class. The class rolled around, and we left together as usual. As we were walking, he turned to me.

“I just wanted to explain why I didn’t call. I knew you were working all day, and I was going to that show with my friend. I knew we’d talk to each other again…”

“Look,” I finally said. “That wasn’t the real reason. I don’t really care if a guy calls me the next day. The reason I told you that is because I didn’t enjoy the sex the other night.”

“Oh,” he said.

“So, just friends?”

“Just friends, okay.”

He didn’t ask any more questions and we went our separate ways. A few days later, I started wondering if I’d made a mistake. The guy seemed perfect in every way except in the sack. I messaged him saying I wanted to give it one more shot. Maybe our problems that first night had been a one-off, and there was more to him than that. He said he wasn’t really interested, that he’d moved onto seeing other people. I told him so had I, and we left it at that.

The most awkward thing was seeing him in class afterwards. We totally stopped hanging out as friends and for a while he avoided me like the plague. It made class super weird and made me realize why they say it’s not a good idea to hook up with anyone you’ll have to see every day afterwards if it fucks up. The weirdest thing of all is that after the class ended he started texting me looking for a quick fuck. I kept turning him down, but he kept asking even as I went through other boyfriends and changed phone numbers. Finally I told him I was pregnant and he backed off.

I don’t know what the lesson is here – maybe it’s to be careful what you ask for. Just because someone seems great at first doesn't mean they're right for you.

Dating Diary: A Foot Fetish?

I’d been casually acquainted with this fellow model at my agency for a few years. The first time we had met was at a Mac Body Painting show where we got to see each other naked. I liked what I saw and I guess he did too, but nothing came of it because he hooked up with one of the makeup artists after the show and I left. Years went by and we ran into each other at a few castings. We would talk here and there but I always thought he was a bit of a mimbo (male bimbo), so I wasn’t really interested. Besides, the only model I ended up dating in all my years in the industry turned out to be gay, which kind of turned me off the idea of dating the male talent in general.

But eventually this mimbo and I ended up doing a casting for an alcohol commercial where we played boyfriend and girlfriend. At the time I was newly single and had just moved back to Toronto, and after the casting we started talking about religion and astrology and for the first time in all my years of rubbing shoulders with this guy I thought that maybe there was more to him than just looks. I gave him my number and he walked me to the streetcar stop. We stood there talking for about an hour as streetcar after streetcar passed me by. It was like I couldn’t tear myself away. Finally I told him I had to go because I was going to be late for work. He gave me a hug and kissed me on the cheek. I was a little shocked.

“Thank you?” I said. Then I hopped on the streetcar.

I was busy for a few days, but we eventually made plans for the following Sunday. Every time I had seen him up to this point was at a casting, so I was familiar with his clean-cut photo-ready look, but on Sunday I was a bit shocked to find out what he looked like in real life – unshaven, with clothing that was a little bit dishevelled and long, dirty fingernails. (I can’t stand dirty fingernails.) He came to my area in Etobicoke and we went to an Italian bakery for lunch, then walked down to the water. He showed me some Tai Chi and I showed him the Kabuki movements I was learning in an acting class. Despite his appearance, I was having a really good time and we ended up going for some Thai food where he made me laugh super awkwardly by singing to me in the restaurant. Mostly it was goofy and fun and romantic, and I didn’t want the fun to stop. After dinner it was getting dark so I asked if he wanted to come over and watch a movie or something. Inside, we talked for a little while and then he asked if he could see my feet.

“No, why?” I said. “Do you have a foot fetish?”

“What if I do?”

I was a little surprised, but at this point I needed to know more.

“What do you do, like, suck on toes and stuff?”

“Yeah, among other things. Let me see them.”

I told him I wasn’t interested because I wasn’t into that. As we continued to talk, a few other things about him came out. He was thirty years old and still lived with his Mom, a pothead, and pretty into the Bible. He still went to church every Sunday and he wanted me to believe too. I don't know how I feel about religion, but I'm certainly not that committed.

I had a lesbian love scene I was working on for my acting class where I had to kiss the other girl at the end. I asked this guy to help me rehearse the scene, but I warned him from the top that I didn’t want to act the kiss out. I just wanted to practice my lines. We ran it through a few times without the kiss, but on the fourth go-round he came over and kissed me. He had great lips, even though they smelled like roast beef and cigarettes, and after we kissed I found I couldn’t focus on the scene anymore. I hadn’t been touched by a man in about four months and I knew I wanted more. We sat there awkwardly for a few minutes, and then I stood up and said I had to run an errand. As I walked towards the door, our eyes locked and suddenly we were kissing again, more intensely than before. Soon our bodies were all twisted together, my legs wrapped around his torso, but then I realized I didn’t want to go any further. We stopped, and I appreciated that he didn’t push the issue.

After he left, I thought about things and decided he wasn’t for me. I was probably just a bit desperate because I hadn’t hooked up with anyone in a long time. In the end, the foot fetish thing was too weird, and I didn’t want a relationship with a grubby pothead who still lived with his Mom. But we’re still Facebook friends and I wish him the best in finding a girl who is also into foot fetishes.

Dating Diary: Norton the Non-Communicator

It started on OkCupid. I matched with a guy who I’ll refer to as Norton, because he vaguely reminded me of Edward Norton. He seemed strange, mysterious, sexy, and intelligent, plus he was Irish. I have Irish heritage, so I’m always drawn to the Irishmen. After some back and forth on the site over a few weeks, I finally gave him my number and we planned to go out on two dates.

At the time I was dealing with some private family stress, and as I was struggling with that, I got sick. The stress brought it on. I had a serious infection and ended up spending some time in the hospital. I was completely out of commission for a week. Once I recovered from the infection, I got sick for another two weeks, and then I discovered I needed to get my wisdom teeth removed. After a month straight of being laid up in bed, this guy Norton was the last thing on my mind, but we kept chatting through the app as I recovered. I felt like through the sickness I was releasing all of the toxins – all of my negativity that had built up over time. It was awful, but it was also cleansing.

I wound up cancelling both of our original dates. Norton said he wasn’t going to ask me out again because a) I kept cancelling and b) I looked like a snob in my profile pic. (I don’t think I’m a snob!) I felt bad so I invited him out the following Saturday. We met at a French place I knew that had a broad menu and was kind of a bar – it was a good spot because we couldn’t decide if we were meeting for drinks, apps, or dinner. I wasn’t hungry so I ordered a fruit salad and a drink, and he ordered a huge piece of meat. (I was worried that he would think I’m one of those girls who doesn’t eat because of how thin I am. But really I just wasn’t hungry.)

The conversation went well – he gradually progressed from being a bit standoffish to opening up and telling me some things about himself. (Must have been the alcohol.) He told me his roommate was moving out. The night went great and we ended up back at his place. I told him casually during the course of our conversation that I was interested in going on a trip to the state of Goa. Later in the evening he flat-out stated that I was going to move in with him and then he was going to come with me to Goa. I told him he was nuts to say that on a first date, but at the same time I was tickled that he’d suggested it. It made me think that he really liked me. We didn’t end up sleeping together – he was too drunk – but I left his place at five in the morning feeling like things had gone really well.

I was busy with work the next day but we ended up on meeting on Monday. I went over to his place and we watched a few episodes of Sherlock. He lived near my work in the downtown core, and it was easier to go to his house than to go home or invite him over. Then on Tuesday we went out again. We had a drink on a beautiful rooftop patio and then went to a movie where I discovered he had a weird thing for Rachel McAdams. He told me that they worked out at the same gym, had had a couple of conversations, and that she even hired him to clean her basement once. The whole thing seemed kind of weird – people get really weird about celebrities. His obsession with Rachel McAdams should have been a bit of a red flag.

We had lunch again on Wednesday before I went to work, but then I started to notice something weird about the way that he was texting me. It was like he didn’t want to keep seeing me, but was texting me just for fun. We would talk back and forth throughout the day, but he didn’t answer my texts when I got off work. When I told him that, he denied it. He said he was already asleep by the time I finished up at work.

I invited him to a keg party on Friday. One of my girlfriends was throwing it for her brother who was going to be leaving to go touring across Canada and I wanted to bring Norton as my date. Before the party we went for Italian food and I made it clear that I was still talking to other guys because we weren’t official or anything yet. He didn’t like that and said he was jealous. At some point he admitted that he’d only had one serious relationship in the past. He seemed to be a little bit off in the way he thought about things, like he wasn't totally there. I think looking back that maybe he had Aspergers’ or something.

I think he enjoyed himself at the party, but it was a bit weird for me to be going to a kegger. I hadn’t been to one in years, I walked Norton home and took a cab back to my place. I was a bit annoyed that he had never attempted to venture into the west end where I lived. The next day we were planning our first official sleepover, and he made a big deal about popcorn. He said he had to get some and then asked me if I had any. When I got to his place he had to run out and buy some because neither of us had any popcorn. It was totally ridiculous. Then he promised me breakfast in the morning.

We didn’t do it that night – it was my time of the month and I didn’t want to do anything. The next morning I woke up before he did and asked him if he had any tea. He said he didn’t. I told him I had to go, and he walked me to the bus stop. I still hadn’t eaten anything and now I had no time to eat any breakfast, so I just grabbed some shitty Starbucks on the way to work. It wasn’t great.

I texted him a few times over the next couple of days, but our schedules didn’t line up so we didn’t see each other. On the following Monday I had my surgery for my wisdom teeth, and Norton asked if I wanted him to come over on Monday night for emotional support. I knew I was going to need some help, but my Mom was coming over to take care of me so I told him I’d be fine. I didn’t want him to see me all drugged up and swollen. The surgery was very unpleasant and my mouth bled for about three days afterwards. It’s not an experience I would recommend to anyone. As I lay in bed recovering, with my Mom taking care of me, I got all sorts of messages from friends and other guys who were flirting with me, all wishing me well. But nothing from Norton. Finally I messaged him to ask how his day was going. I was upset – I had thought he really liked me.

This is the reason you're single and why you've only had one serious relationship, I told him.

I said that I wanted to be with someone who showed me he could fit me into his life, not one that just says he wants me in his life. It takes effort to make a relationship work – a guy has to cater to a girls’ needs sometimes. He told me he had been golfing all day and went to dinner afterwards with work friends and was too busy to text me. It didn’t seem good enough. I was done with him.

It was a good-bye fight, an I’m-going-to-move-on-with-my-life fight, but that wasn’t quite the end of Norton. In the end he won me back and we started dating for real. I even moved in with him for a few months. But after a while, the Aspergers and the inability to communicate just got to be too much. I broke it off with him and found my own condo downtown.

Dating Diary: The Perfect Pickup Goes Sideways

This was probably one of my weirdest pickups ever.

The story starts by me taking a Thursday mid-shift. Normally I worked nights, but on this day I swapped it for a shift that ended at 9 PM, which worked out perfectly because I wanted to go to a Second City party that night (I was taking improv classes there). Once I finished up at work I headed straight to Second City, sat down at the last remaining seat at the packed bar and ordered a drink called a Moscow Mule (a vodka and ginger beer cocktail). The Moscow Mule is my favourite drink – if I had a choice, I’d never drink anything else. I hadn’t seen anyone from the party yet, but I thought maybe I was a bit early. I texted my friend and found out that I’d gotten the date wrong – the party was the following Thursday. 

I thought: well I have NOT EVER drank in a bar by myself, but since I already ordered my drink I might as well finish it. As I sipped it, two separate guys came over and tried to hit on me. I basically shooed them off. After the second guy left, the guy sitting next to me eating and watching the baseball game turned to me and said, “I’ve counted two so far.”

“What?”

"Two guys trying to pick you up in the first ten minutes since you sat down - that's pretty good."

He was tall, maybe 200 pounds, with curly dark hair, a nice smile and steel blue eyes, and dressed in a suit. He ordered a Moscow Mule - my drink - and started chatting with me. Apparently he had just gotten off work and lived across the street. He was a designer, and just so cute and smart and funny. He seemed a little insecure, which just made him seem available. It seemed like we liked a lot of the same things. In the back of my mind, I was thinking, this guy is so perfect it’s cray. He told me he had squash in the morning and then he said he should make sure to grab my number before he forgot. Once we traded digits, it was like bang. The Jays game ended and he quickly downed his drink, paid for both bills and ran off. I was left sitting by myself at the bar, thinking what the fuck just happened?

I wasn’t planning to text him the next day. Like, who knows what that was? But at some point in the afternoon he texted asking if I wanted to grab a drink on Friday night. I had to work but I agreed to meet him afterwards. So at midnight on Friday he picked me up in an Uber and took me to a bar that had live music. He told me it was his favourite spot. I had to pay for the drinks because he wasn’t carrying cash on him. (Totally fine.) Then we went to a super-nice bar where we sat and gabbed till close and he covered the bill.

We went back to his place. It was sort of empty - not a lot of furniture in the living area. Definitely a guy's place. He offered me a joint. I turned it down but hung with him on the balcony while he toked. He was playing all sorts of music and it was all the same things I loved. It all felt so comfortable. We watched videos, listened to music that moved our souls, and just sat together. Eventually he asked me if I wanted to watch a movie with him in bed and I said yes. After we turned it on we starting making out. Everything was going great, but at some point I had to pump the brakes. I realized I wasn’t ready to sleep over or sleep with him yet. I told him I had to go. He didn't seem super thrilled about it, but he walked me to the door. As he showed me out, I got a bit of a rude, sarcastic vibe from him. He sort of half-jokingly shoved me out of his apartment at the last minute. It seemed weird at the time but I didn't think too much of it.

The next day I texted him and he asked me when I was done work because we had to finish watching the movie. I told him, and again he came to pick me up in an Uber. We went back to his place and chilled again. He got stoned again and I just hung out as he showed me some of his artwork and some various videos online. I don’t think we actually watched the movie we’d started the night before. I went up to his bed again, but it was late and we were both tired so nothing happened between us. As I lay there, he wrapped himself around me like he had to hold me tight. He was like a bear protecting me. I couldn’t leave the bed. He rained light kisses on my neck and the whole experience was just so sweet and charming.

The next morning shortly after I woke up I had to leave for class. He was still wrapped up around me and asked me to stay a little longer. We started chatting, and then he said if we didn’t have sex now it would never happen. I thought he was joking. I had to get to class. I got up, kissed him on the forehead and teasingly said, “then it’s never, my friend.”

As I was leaving, I called up “bye” from the main floor and got back a gruff response like, “yeah, we’ll talk later.” It seemed weird but I shrugged it off at the time. Later in the day I texted him with a joke I thought was funny. He didn’t respond. I waited for a while and just…nothing. He was gonzo - a ghost.

I was left wondering what I'd done wrong. I felt like I was terrible at dating. Was he really just after one thing all along? Our two nights together had seemed so sweet and lovely, and then it was like - no sex, I'm out. I know now that it was selfishness on his part but at the time I spent a lot of time wondering if it was something I had done that had ruined it. 

Time passed, I saw some other people, moved on, and almost completely forgot about him. Then one day I was bartending at work when a familiar face sat down and ordered a drink. 

“I feel like I know you,” I said.

“Yeah, I met you at the Second City bar,” he said.

“Oh, yeah,” I said, suddenly recognizing him. All the feelings I had pent up from that week suddenly came rushing back. I felt myself losing control and I'm sure my face turned a fire-engine red. “And you never messaged me again.”

After I said that, I had to get someone else to cover the bar for me until he left. It was upsetting. I felt a bit used. Like all that niceness we had built up had been for nothing – in the end he was only after one thing. Thinking back, I remember how unfurnished his house was. I've seen other guys who were just as single-minded, and it seems looking back like they always had totally vacant houses. It makes me wonder if that’s a red flag when it comes to guys. Like maybe empty houses mean empty hearts? Maybe sometimes the guys who don't have enough love for themselves to turn a house into a home are the ones who aren't capable of having a relationship in the first place.

But who knows?

Dating Diary: The Angry Artist

Here’s another doozy of a dating story. You can’t make this shit up.

A friend I worked with named Peter had some art done by a local tattoo artist. I saw the tat after he got it done and immediately fell in love with it. Peter told me that the guy who did it was amazing and super chill and down to earth. He told me he was Asian and had tattoos all over the place and hinted that I might really like the guy. I do have a soft spot for Asian guys and tats, but when I first went to see him I was more interested in getting some of his art.

At first, I emailed him to ask about getting something done, but I didn’t hear anything back I added him on Instagram and thoughtlessly liked a bunch of his posts. Like I said, he was an amazing artist, and I wasn’t even thinking about the fact that he could see who was liking his stuff. He added me back and suddenly I noticed that he was liking a bunch of my posts.

“Is this a liking contest?” he messaged me.

I told him I loved his art and had emailed him about a job. We set up an appointment and I went into his studio for a quick look and to set up the actual appointment. In between the meeting and the appointment we texted back and forth a bunch. It was mostly just about the artwork but I tried to flirt with him a bit. He was a hottie.

On the day of my appointment we hung out for about three hours, just talking about everything. I thought that he was fun and interesting and seemed to be into all the same things as me. I was totally into him. I thought we had connected and was waiting for him to ask me out, but he didn’t say anything that day. Over the next couple of days we texted back and forth. I told him I was very intuitive and he asked what I was thinking.

“I think you want to ask me something but you’re holding yourself back,” I replied.

“Wow. UR Psychic.”

“Look if you want to ask me out just do it.”

“I don’t know. U might think I’m boring LOL. Lemme sleep on it.”

“Fine, whatever,” I said. But I was thinking, Are you kidding me?  He certainly wasn’t boring, but that whole exchange was a bit of a red flag that he was a bit weird. I waited all day the next day to hear something and then in the evening I finally texted him something like, “if your heart is telling you you should then you should.” He got the message and finally asked me out.

Our first date was probably the best date I have ever had. We had brunch at a lovely little place that my friend had recommended and then went to the valley by Old Mill subway station and watched the salmon migrating upstream for about five hours. We didn’t kiss, but the whole experience was amazing.

Over the next few weeks the guy was just such a sweetheart. I had had a few too many bad experiences and had resolved to try and wait a month before I slept with anyone. With this guy, it was easy to play it off as inconvenient at first because my Mom was staying with me at the time and he still lived with his parents while he saved up for a studio, so a “sleepover” would have been awkward. Most guys seemed to give up and leave long before we had made it a month, but this guy just stuck around. I enjoyed hanging out with him tons. He was so affectionate, loving, friendly, chilled, and easy going. Just lovely. He only texted me which caused a few misunderstandings because I like guys to call me as well. But he was great. With everything going so well, after the first couple of weeks it was getting hard for me not to sleep with him and hard to explain why I wanted to wait. Even though a month isn’t that long, in the modern world it feels like a lifetime, especially for men.

Finally it happened. We had made it about a month so I went to bed with him and the first time it…wasn’t that great. It was fine, but there was nothing memorable or exciting about it. The second time, though, was different. The tender guy I had been falling for turned into a completely different person. He went at me like a jackhammer, smacked me in the face, and called me dirty names. He tried to strangle me and talked way – WAY – too much throughout the entire thing. I let him finish and thought – nope.

I didn’t say anything about how I felt immediately but a few days later I brought it up over text. (I had wanted to talk it over in person but he didn’t want to wait until we met up.) I told him that I didn’t like it like that, and that girls who did probably think about sex differently than me. I even suggested that maybe the girls who do have had some sexual abuse in their lives (I’m not saying that they necessarily have, but that was my personal opinion at the time). And even if I had been willing to go along with some of what he did, he needed to bring it into our relationship way slower – one thing at a time – and warn me in advance about what kind of stuff he was going to be pulling out. Even then, I don’t know if I would have been into it. But at least I would have been willing to try rather than noping the fuck out.

After I told him all of that, he told me he was super embarrassed and sorry. He told me his last girlfriend had been into some crazy shit and he had transferred it over to me. He told me he could go along with whatever I liked. But I’m not like that. I don’t want to direct the whole process when I’m in bed with someone. I’ve never had to do that and I didn’t really want to start.

The question of whether we could make it work simmered for a few days. Finally I asked him straight out, “Is that what you’re into or not?”

He got angry and defensive, and I realized things would never work between us. A few days later we officially ended it. I never slept with him again, because I just didn’t think that I would enjoy it. We’re still friends and I think he’s a great guy and an incredibly talented artist. I don’t hold any of it against him. 

But sometimes two people are just incompatible…

-Sarah

When A "Dating Diary" Isn't Really About Dating

A couple of weeks ago we posted a video categorized as a “Dating Diary” in which Sarah discussed an experience she had where a man posed as a producer offering her a part as a way of trying to get into her pants. Since that time, Sarah has realized that this was not a dating story at all, but something much darker. In light of all the sexual assault allegations coming to light recently against Harvey Weinstein, Kevin Spacey and innumerable others in Hollywood and elsewhere, it’s important to recognise the line where things stop being professional and become abusive, and enforce that line. This is one of Sarah's (far too many) stories. In this case, she did go to the police - too late to actually press charges, maybe, but early enough that the next time this happens it will be a black mark on his record as he will be seen as a repeat offender.

#metoo

Dating Diary Vlog: The Man Who Wasn't Camera Shy

Hey followers, since we didn't post a fresh article on Monday, here's a bizarre dating story about an experience Sarah had with a "producer" who offered her a role in a movie...

Dating Diary: The Blond-Haired Englishman

A few years ago I put myself in a very weird situation. It all started one night when I was out drinking with the guys and a tall, thin blond man with an English accent approached me. I was polite with him but not interested because a) I was busy with my friends and b) tall and skinny and blond is not my type. After I gave him the cold shoulder he started chatting up one of my guy friends (I didn’t really notice because it was a standing bar and everyone was milling around) and when last call came and we headed back to a girlfriend’s place, the blond tagged along. The group chilled all night and I ended up chatting with him a bit. At that hour, he seemed cute and interesting, and when he asked my number, I gave it to him (partly because I was into it, but mostly because at that stage of my life I was terrible at saying no to any man who asked for it – thankfully, I’m better about that now). When I had to leave and he made to leave at the same time, my girlfriend pulled me aside. “Do you like this guy?” she asked. I told her I didn’t and she rushed me out before the guy could follow and try and get me back to his place.

He went back to England and we texted back and forth and Skyped a few times. Neither of us seemed that interested in making things happen. It’s hard for me to fall in love long-distance – I feel like I need to see, hear and feel a lot of interest coming from a man before I’m engaged. But a few months after I had first met him he mentioned he was coming back to Toronto on business, and he suggested we see each other. It seemed like a good idea but the timing was bad for me – I was scheduled for three straight 12-hour waitressing shifts (11 AM-11 PM) on the weekend he was coming. I told him I would try to see him, but deep down I knew I wasn’t going to put in much effort. Once he got to town he texted me several times. I felt bad and agreed to meet him after work. I was very tired and felt sticky and yucky from a long day in the restaurant, but we chatted for an hour or two and then I went home. The next day he again met me after work. This time we went out drinking until last call and then I went back to his hotel and talked some more. He was a complete gentleman – he didn’t even try to kiss me. I crashed on his bed for an hour and then I went home to clean up and get ready for work. He gave me a little peck on the cheek and headed back to England.