This week, a newly single woman, mixing business with pleasure at her tech job: Day One 7 a. I wake up and go to the gym in an attempt to burn off the mistakes of the weekend. I listen to my morning podcasts and arrive at work, exhausted. Luckily for me, my company is based on the West Coast, so mornings are typically slow. I grab some cold brew and start working on a presentation I have to give to the entire company in a few weeks.
I have to admit, I never thought twice about him, and our first encounter happened by total chance. Ugh, there he is. I start going through Hinge to distract myself … but none of these guys seem appealing. Andrew texts me, confirming plans for tomorrow.
We met on the League and then had an amazing eight-hour first date. Since I just got out of a very long, serious relationship, I know I should keep things casual. But I would basically marry this dude if I could. I run into Matt in the kitchen and wish him a happy birthday. Why does every non-sexual encounter feel so awkward? I tell Matt I have a birthday present for him. We met at a bar and were together about four years — probably moved in together way too soon.
We had a ton of issues he was kind of a controlling dick , yet he was totally blindsided by the breakup. Day Two 10 a. Eating lunch, and Andrew texts me to tell me how busy he is. Is he trying to blow me off? Andrew suggests meeting at a place downtown at 7: Matt is sitting at the desk across from me, chatting with one of his friends. Stop torturing me, guy! I arrive to my date and feel super nervous. What happened to the cool girl I was on our first date?
Why do I psych myself out like this? We are on our second drink when we start getting handsy and making out. At the next bar, we continue making out, joking about future plans. Then, he asks about my tattoo. I should just brush it off and give some surface-level explanation, but I tell him the meaning behind it.
I guess my nervousness got the best of me, and I continue to ramble on about my life story. The date is going to shit. We end the night. He kisses me good-bye and asks me to text him when I get home. I am so tired. My friends want to murder me. I need to get over it. Oh well, at least I have Matt to look forward to. I have an afternoon coffee and prepare for the networking event that I am reluctantly attending tonight. I really want to put myself out there, make connections, and excel in my career … but this shit is exhausting.
She invites me, and I gladly accept. Drinks turned into dinner that turned into more drinks. I am small-talking with this New Hottie and feeling much better about myself and the disaster of last night. Everybody decides to go home, and I ask New Hottie if he wants to grab another drink elsewhere. He has a tattoo that looks like a tribute to his dad. I decide not to bring it up. He starts going down on me and sticking his fingers in my mouth. Oh my God, he is so fucking good. I come really hard.
I give him head, he comes, then he tells me that he can get hard again and fuck me right away. Where has this guy been all my life?! He was letting his starving-artist friend stay the night, but we slept through all 16 of his calls. In a total daze, I get up, get dressed, and order an Uber. His friend shows up before I can make my escape, and apologizes profusely, encouraging me to stay. I kiss New Hottie good-bye and bolt the fuck out of there. That sex was so good. I get ready, head to the office, and put my head down in work.
She suggests we go to a sex store and buy something. Matt and I have had some kinky sex … a little hair pulling, choking. I buy a pair. He cabs it to my place. We start hooking up. I can feel his hard-on through his sweatpants. God, I missed his dick. I handcuff him and start riding him. He loves being submissive.
I eventually let him get on top, and we continue having sex. Is he actually into me, or does he just not know to fuck and bounce? I want the casual sex, and am down for avoiding the serious talks — but nobody wants to feel completely used. He reluctantly leaves because we both have early meetings. I welcome the sleep and pass out in a buzzed, sex-induced coma.
Day Five 7 a. I am exhausted, but not hungover. I wake up, head to the gym, and take my morning meetings from home. Matt makes eye contact with me when I walk in. Less than 12 hours ago, he was handcuffed in my bed. And now here we are, co-existing in this office, like nothing happened. Headache starts to creep in. I am SO tired now. Sarah comes to see my apartment, and then we head to the park. We sit at my favorite secret park spot by the lake, chatting about life and laughing away.
I wish she lived in NYC. Sarah goes out with friends, but I decide to go home. I order in some Greek food and eat while reading The New Yorker.
Eventually, I make some detox tea I really need to flush out all of this alcohol , watch some SATC, reply to my boring Bumble and Hinge matches, and pass out. Day Six 9 a. I love waking up not hungover! I throw on my running shoes and do the Central Park loop.
I walk to an art studio near my apartment. He seems interesting and attractive. I grab a pre-date drink and apps with Nikitha, and meet Dave at a wine bar. I walk in, and there he is. This cannot be real. I reluctantly sit down. I ran a 10K this morning and this guy is having an emotional meltdown over his ex, eating God knows what.
I still have a glass of wine, politely decline a second, and leave. I meet my friend Jon and another friend for drinks near Union Square, where I quickly down two dirty martinis.
We left the party and are now making our way to some speakeasy.