The Executive Recruiter With an Unemployed Lover

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New York's Sex Diaries series asks anonymous city dwellers to record a week in their sex lives — with comic, tragic, often sexy, and always revealing results. Check back Sunday nights for your weekly peek behind doors left slightly ajar. This week, an unlucky-in-love recruiter in a monogamous, three-month relationship: female, 32, Ditmas Park, straight.

DAY ONE

10 a.m. I’ve never been lucky in love, as they say. I was bullied in high school, largely because my twin sister was a legit “nerd” and everyone assumed I was, too. This made getting a boyfriend impossible. I had a four-year crush on one guy who would make out with me occasionally on the bike path home and then deny it to his friends — it was pretty brutal. None of that should matter now that I’m 32, other than to illustrate that I don’t have the best self-confidence when it comes to men. My only real boyfriend happened between ages 27 and 30: He was a simple guy; our sex was meh. He moved back home to Minnesota and that was that. Two years and practically zero dates later, here I am, dealing with “Davis,” a guy I met on the Q train three months ago!

Noon Davis and I meet for lunch at our favorite counter-only café. We go out to eat a lot, and I pay for us every time, but it’s not as bad as it sounds … I  have a lot more money than him. I have a solid savings, some help from my family, and a great job as a freelance executive recruiter. He has no job. He is 40 years old, a so-called photographer, but he never pursued anything … a gig here or there. I think he’s depressed — not because he seems depressed but because a complete lack of ambition seems like a symptom of depression. Nevertheless, Davis is incredibly kind, deep, honest, and sensual. He is broke, yes, but I try not to give that too much power. I urge friends not to write him off as a loser. At lunch today, we eat, talk, and laugh — three things we do exceptionally well. The fourth: sex!

3 p.m. Two rounds of hot sex at my place. Before Davis, I hadn’t had sex since my ex — two years ago. Davis brings me to orgasm every time, often twice or three times. He is so focused on my body. His penis is big and friendly and strong.

4:30 p.m. Davis falls asleep in my bed after sex, while I hop on the computer to work.

7 p.m. We go to another restaurant in my neighborhood for some dinner. Our bodies are spent from afternoon sex, so we say good night after dinner.

10 p.m. David texts me good night and sends a selfie from his bed. He is so sweet and handsome. We haven’t labeled ourselves yet, but a few weeks  ago we assured each other we were monogamous. I still insist on condoms (he does not mind).

DAY TWO

9 a.m. I am lucky that I can work from home on most days. I make coffee and get to it. Davis texts "good morning" with a selfie. He does the "good morning/good night" thing every day.

3 p.m. I worked a few hours and feel like I can step away, so we make like Europeans and have an afternoon vino and siesta. We meet at a bar for carafe of red wine and some olives and nibbles, and then go home to have sex. Davis has taught me so much. He took me to a sex shop last month and helped me pick a vibrator (I paid for it); today, we use that on me. He fingers me with the vibrator on my clit … simultaneously, he sucks, almost bites, my nipple. I try to give him a blow job after, but he is more of a giver than a taker.

6 p.m. I kick him out so I can finish my work. My period is coming any second now, anyway.

10 p.m. He FaceTimes his "good night" from bed. “Hey, babe,” he says. When he calls me babe, I melt. If this guy weren’t broke and unemployed, I would feel like the luckiest girl in Brooklyn. I go back and forth about how much his work status matters. The fact that he has no money matters very little (to me at least); the fact that he can’t hold a job, nor wants to, is the red flag. I vow to bring this up — to dig a little deeper — in the next few days.

DAY THREE

9 a.m. I spend the day at a client’s office. So many people hard at work. It makes me turned off by Davis. All these men would rather be home in sweatpants, too, I’m sure, yet they know work is important. Work is a thing. How did Davis not get the memo?

7 p.m. I take the train home. I’m tired. It was a long day with lots of meetings. Davis wants to grab dinner; I don't want to see him tonight. I say I have a bunch of work to do … and I rather enjoy rubbing it in (albeit in a very passive-aggressive way).

10 p.m. I have guilt. If Davis’s lack of work is actually a condition of something deeper, something sad or broken inside of him, I should not treat it this way. I text him that I’ve missed him all day. He texts me a few times. Babe this, babe that, and "good night."

DAY FOUR

9 a.m. I’m meeting my best friend for coffee. She is on maternity leave, and she brings the baby. I want kids — and considering Davis is so good-natured and handsome, I have imagined kids with him. But — I know I sound like a broken record — isn’t having kids with a man WHO DOESN’T WORK completely unfathomable? Best friend says: YES. It irks me that everyone writes Davis off so fast since he doesn’t have a job. What about all his other qualities — his warmth, depth, etc.? I am guilty of it, too, though. Ahhh … I got my period and I’m all over the place, hormonally.

1 p.m. It is a quiet workday. Davis and I decide to meet at our favorite counter. I want to talk; I just don’t want to be insulting — it’s such a tricky subject. I blab a bunch of words … basically, “I don’t care about the money, I’m worried that your lack of work is reflecting something deeper, something you might want to talk about.”

He handles the talk well, but he seems slightly embarrassed. He also doesn’t really have an answer for me. He says something about possibly being afraid of success, and something else about not having the guts to put himself out there. He also told me he’s like the superintendent of his building — which is how he affords to live there. He called it “odd jobs in the building,” but I think he meant he’s the super. I’m okay with that; it’s good, honest work.

3 p.m. Neither of us feel horny after lunch. I tell him I have my period anyway, and he lifts an eyebrow. Davis is kind of into period sex. I tell him to come by later tonight. I have hours of emails to respond to.

8 p.m. He comes over. Towels on my bed. Period sex. It’s not too messy and I do have to say, it feels incredible. We shower off together after. No mention of our talk at lunch.

DAY FIVE

9 a.m. Davis slept over. I ask if he can run out and get us some coffee since I’m out of beans. He says yes but hesitantly, and I realize he has no cash. Not even two dollars to get two coffees. He also doesn’t “believe in” credit cards. I try very hard to play it cool and I tell him to grab my wallet. I’m so annoyed. It’s NOT okay to not have enough money for a fucking coffee. It is not caviar.

9:20 a.m. He returns with our coffees and I tell him I have tons of work; he’s gotta go. I can’t hide my annoyance but we both pretend it’s not there. He takes off quickly, kind of pathetically.

10 a.m. I get to work.

5 p.m. I’ve ignored his texts all day. I feel bad but I’m still seething from the coffee. I need to choose to be okay with his situation, or break up with him. Accept him or end things. I so don’t want to end things!!!

9 p.m. I go to bed pretty early, still giving Davis the cold shoulder though not communicating why.

DAY SIX

Noon It’s the weekend. I have a friend’s birthday dinner tonight, and I already know I can’t bring Davis because it will end up being $60 dollars a person (or so) and I just can’t put him on the spot like that. I tell him I’ll come over after. After two glasses of wine, I know I’ll want to.

7 p.m. I go to the birthday thing. No one likes these group dinners! And actually, it comes to $75 per person.

10 p.m. I Uber to Davis’s apartment. He’s reading in bed. He smells great and holds me really tight. After hours of superficial conversation at dinner, it feels so good to have some real intimacy with him. We kiss a lot, and I actually get off from “dry humping” him. I don’t want period sex on his sheets … it’s just too much. I fall asleep in his arms.

DAY SEVEN

11 a.m. I head home and take a long autumn jog. This is what I realize on the way: Since money is not really an issue for me, I am going to try and get over his situation. He seems comfortable with who he is, so who am I to judge? Also, he is good to me. The sex is phenomenal. I trust him. And I believe he has a very pure heart. 

Noon I return home from my jog happy with my decision. Stay with Davis and accept him entirely. If I accept him entirely then maybe my friends will, too. If not, who cares.

7 p.m. We meet at a new wine bar in the neighborhood. I am always happy to see his face. “Hey, Babe,” he says, kissing me on the lips, as we start off another lovely night …

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