sex diaries

The Woman Secretly Dating a Professor She Works With

Illustration: Marylu E. Herrera

This week, an event planner who’s wondering if it’s time to expand her dating pool: 34, single, Boston.


8:30 a.m. I work at a university doing events, so my summers are a good time to refuel the tank.  For me, that means waking up, making coffee, and sitting on my porch and reading. I’m surrounded by really smart people and often I feel self-conscious about not being well-read enough. Today, I’m trying to finish The Sympathizer.

9:30 a.m. I’m seeing a professor at the school I work at who has been divorced for about a second. It’s hard to go even an hour without checking to see if he’s texted. The last time I saw him was a few nights ago, when he came over for a “booty call.” We both knew that’s what it was. We had some wine and fucked on my screened-in porch. I came while riding his dick for about one minute — that’s how attracted to him I am — and he came while fucking me from behind.

I’ve wanted him since the day I met him at a work function, about four years ago. We first hooked up about three weeks later, and have had about several secret but non-scandalous flings since then. His marriage was always falling apart, and they don’t have kids, so I never felt any guilt about it. And I have no delusions that he’s going to bounce from his marriage to me.

1 p.m. No text yet. I’m in a constant state of waiting to hear from him. This state of mind has gone on, again, for four years. It’s very uncomfortable. I do date other people, but I’m pretty much addicted to him.

3 p.m. I have errands around town. Target, the grocery store. I listen to podcasts as I drive around, call my mom and my sister-in-law to check in. They’re all in California, where I’m from.

6 p.m. I know he’s not going to text today — he would have done it by now. I go pick up some Thai food and settle in for the night.


9:15 a.m. Today should be interesting because I’m running a photo shoot at the school with the professor in the center of it all. We’re highlighting his department.

10 a.m. I work very hard on my hair and put on the perfect summer dress. Effortless but sexy. My legs and arms are a bit tanned and I feel really pretty, to be honest.

I’ve had four long-term relationships since college (of about two to four years each), but it’s been hard to date since meeting the professor because I’m so consumed by him. I’ve had sex a few times with other men in the last few years, but they can’t keep my attention.

12 p.m. We’re all in a big event hall and he’s there talking to colleagues. We do a double kiss hello on the cheek. I swear, I could cum just from that.

What I love about the thing with him is that he does flirt with me in public. It’s not like I’m pushed aside. He doesn’t hide his affinity toward me. My friends think I’m the one giving mixed messages. Cold and distant when we see each other during the day, hot and slutty when we meet up at night. But I’m walking a tightrope … I don’t want to mess with my work life, and I also fear looking needy or desperate.

2:30 p.m. Well, that was pretty boring. I like my job because of the stability and it pays well. I used to work for a very stressed-out wedding planner in New York, and I’d never go back to that kind of pressure cooker again.

2:45 p.m. As we all say our good-byes, the professor asks if I want to have dinner later. I tell him yes, but to text me with the details. I don’t want to discuss it at work. A little later he texts about a wine bar, and my body is on fire.

7 p.m. We meet up. I can tell he’s horny. My dress today did the trick. We have some wine, a few small bites, and head to his place. I’ve only been there once, but his ex-wife has moved out and it’s safe to go now.

8 p.m. We’re fucking in his bed. This is a first. I ask — mid-fuck — if it’s weird for him, and he says we can talk about it later.

9 p.m. We’re having tea on his back porch and he starts talking about the divorce. It’s the most he’s ever shared with me about his marriage and the inner workings of it all. The more he talks, the more anxious I feel. He’s still struggling with it. I don’t like to hear that. The wound is still open, unhealed. I try to be a good listener and a good friend, but I actually just want to cry. This guy is not going to be my boyfriend. Not today, probably not ever.


7 a.m. I wake up feeling sad.

9 a.m. Grab a coffee with my friend and we walk and talk. She knows all about him. Her main concern is that I should have kids soon, and I’m just so stuck in this weird thing with him. I definitely want kids. I’m only 34, but I know I have to figure out the plan soon. Either I have to really date around and meet someone to start a family with, or freeze my eggs, or plan to have a baby on my own. I know the first thing I need to do is free myself of the professor thing, though.

2 p.m. Redecorating my little house. I post some pictures on Instagram of my artwork and cool ceramics. The house is looking very chic, I have to admit.

5 p.m. I make myself a big salad and open up a bottle of chilled white wine. I’m going to rejoin some dating sites tonight. And I’m not going to text him.

8 p.m. There are really, really terrible options out there. I matched with a few not-horrible people, but sheeeesh, this is not looking promising.

10 p.m. Today was a bummer. Let’s hope I can sleep it all off.


9 a.m. It’s a beach day with some friends. They’re all bringing their kids. I’m fine with that — I love kids! Feeling a bit vulnerable and hope I can get my spirits up, but otherwise, I’m excited.

12:30 p.m. We’re all set up on the beach. Good food, drinks, books. The kids are all playing nicely. It’s lovely. All the couples want to know about my love life. They don’t work with me, so I can tell them about the professor and not worry about work gossip. Everyone says he’s bad for me. One friend says I need to work on my self-worth. It stings to hear that, even though she’s probably right.

5 p.m. One of my favorite things to do after the beach is to take a shower, put on pajamas, and chill. I love the feeling of being sun-kissed and tired and lazy. I do this and then I look online to see if any of my matches panned out.

6 p.m. Professor asks if he can stop by. What’s one more harmless fuck?

7:40 p.m. He knocks on my door. Because I know that I’m ending this soon, and I think he knows that I’m pulling away, the sex is extra-passionate. It’s a bit rough and super-intense. I’m wetter than usual (didn’t think that was possible). He goes down on me ferociously and then we fuck hard.

9 p.m. Lying in my bed, he asks if he freaked me out talking about his marriage like that. I say, “A little bit, yeah.” He apologizes. But in this moment, we both know that we can’t give each other what we each need. I don’t want to be his therapist. He’s not ready for another serious relationship.

10 p.m. As we hug good-bye at my front door, I fight back tears. I will miss him so much when I get the courage to end this.


10 a.m. Work Zooms. I can’t believe the summer is halfway over!

11:30 a.m. I do some online shopping. Would love some new items for fall. Maybe some new clothes will make me more excited to go on dates with these online guys too. I actually have one drinks thing set up for tomorrow.

3 p.m. I stop by a pet store. I’m thinking about getting a dog. These puppies are so cute! I’m dying over them. But the store feels icky and I have guilt about not getting a rescue, so I leave.

6 p.m. Sushi delivery!

8 p.m. In bed, reading. A nice, calm day.


10 a.m. It’s not prohibitively hot out, so I take myself on a nice long hike. I like to listen to comedy podcasts when I do this. It’s good to laugh while pushing my body.

1 p.m. Make a big sandwich. I’m starving!

2 p.m. Start to think about what to wear tonight to meet Michael, the Tinder date. He seems really nice and pretty cute too. He works in politics, which is interesting, and that’s about all I know!

4 p.m. In the shower, I masturbate and try to think of anyone but the professor. I close my eyes and think about a celebrity — it works!

7 p.m. Michael is at the bar waiting for me. He’s very … clean. That’s my first impression. Freshly shaven. Smells good. Professor is more of a scruffy-intellectual-looking type. Michael’s not hot, per se, but he’s perfectly fine-looking too. We start to talk. He seems nervous but also very friendly and warm.

9 p.m. The date is over and we hug good night. I’m not dying from the sexual chemistry, but I’d definitely see him again. He tells me that he’d love to do it again too. We hug good-bye one more time, this time with a bit more heat, and walk away toward our respective cars.


9:30 a.m. Michael sends a “good morning!” text. It’s one of those things that’s cute if you like someone and annoying if you don’t. I find myself charmed by it. I write, “Good morning to you too!”

12 p.m. I feel a little lighter on the inside today. I’ve been thinking about the professor a little bit less. He texted me while I was on my date last night and I ignored it. That wasn’t a strategy; it was simply because I was distracted. I don’t plan to text back, but we all know this is a “one day at a time” situation.

3 p.m. I’m getting a pedicure and my eyebrows waxed. A good waxing always feels like a spiritual rebirth of sorts.

4:30 p.m. Michael asks about tomorrow night for a “proper dinner together.” I tell him, “I’m in!” From there, I let him steer the ship and pick the place. It’s nice to be courted. The one problem is, I haven’t looked online since our first date. It’s not that I’m smitten by Michael … not at all. I’m just such a one-man woman, I can’t really engage with more than one at once.

7 p.m. The professor texts, “Are you mad at me?” I don’t want to ignore all his messages. But I don’t feel like feeding into them, either. I write back something about how I’m not mad at him at all, but that I’m also looking for a healthy, real relationship, and I’m not sure if he can be that person for me right now.

8 p.m. I’m shocked by his response. It’s something like, “Don’t underestimate me, please.” Are these mind games? Is this bullshit? It’s a little emotionally exhausting, honestly.

9 p.m. I put my phone down and decide to revisit this tomorrow. Everything is always better after a good night’s sleep.

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The Woman Secretly Dating a Professor She Works With