Sex Diary: Awkward Groping, Meh-Makout, Ex-Tension, & An Emotionally Ambiguous Cuddle

Welcome to the Frisky “Sex Diary,” in which an anonymous person shares the details of her sex life over the course of a few days. Sometimes these entries are filled with revealing romps, while other times there is nary a naked moment in sight. Some of these diarists are frequent contributors. Want to share a page from your sex diary? Email [email protected] All entries will be anonymous.Diarist: College student in her early 20s, stuck in her college town for another semester. Single-ish.


8 pm: Drinks with J, the new guy I’m dating, before going out with E, my (male) best friend for four years. It feels like an awkward first date even though we’ve already slept together. About 45 minutes after we get to the bar, J’s buddy comes to meet us, because he got stood up on a date. I’m almost relieved because I need to make an exit.

10 pm: Make excuse to J that I have to go do homework, but really make my escape to pick up E. J texts me after I’ve left, wanting me to come back. We haven’t slept together in three weeks. I say I can’t, I have to go to the library.

10:30 pm: E and I take Everclear shots, head downtown before they kick in. I can tell I must look good. He is staring. We hit a dive bar; he buys my drinks. He looks good in a button-down. Later on that night, this awkward bar girl asks me how long E lasts in bed. I drunkenly tell her he’s good, that I’m in love with him. At least one of the two is true! (We haven’t slept together, so how would I know?) Also, Long islands? Yes, please. Possibility of driving home is gone. I am OK with this. Decide to either sleep at E’s or just wander to J’s for post bar sex.

12:45 am: Texting J, who is suggesting sex in the stacks at the library. I wouldn’t say no to that. Bucket list. Instead, E and I walk back to his place. I plan on crashing on his futon, so I throw off my boots. E asks me to cuddle. I can’t say no to him. He strokes my arms and sides all night, but we never even kiss. I wake up at 4 am, realize I am still in E’s bed, and that I am in trouble.

7 am: Roll out of bed to go to bathroom. Settle back in on other side of bed. E rolls over, wraps arm around me. Uh oh. Just. Kiss. Me. Already … Nope, back to sleep.

9:30 am: E complains about getting out of bed with me, but after getting ready, we do the walk of shame back to my car. We talk about our standards – how we need them. We don’t discuss us. I drop E off at his car. F**k. F**k. F**k.


3:30 pm: I wake up super late, decide to get a tattoo. One hour and $80 later, I am a happy girl and have a religious tramp stamp.

7:30 pm: Dinner for the best friend’s birthday. I’m sitting next to a former hookup at dinner. Said hookup is referenced. Awkward! After dinner my friend and I make plans to go to our new favorite bar. I hope to meet someone interesting. Instead, we get face time in with some frat boys we know and they buy us Lemon Drop shots.

11:10 pm: Text from this photographer I know, asking what I’m up to. I have avoided hooking up with him because he acts like a child. I text him back anyway and return to dancing. The photographer continues texting me all night and eventually makes an appearance at my bar. He convinces me to dance with him. He has no rhythm. I wonder if this correlates to his abilities in bed.

1 am: We all leave the bar. The photographer asks me for a ride home. I realize there is a potential for sex here. He asks me if I want to come over, but I tell him I need to go home and he can come with. When we finally get to my place, I discover my roommates are sleeping, but I’ve lost all interest in having sex. Just want to go to sleep. He tries to validate me, tells me I’m beautiful, compliments my work. I am not having it. We sloppily make out, but that’s it. I’m a sucker for a good kisser. We go to sleep and I discover he likes to cuddle, and snore.


8:30 am: Kick the photographer out of bed so I can go to church. Seriously.

9:30 am: Something in church stuck with me. I need to be a better person, I tell myself. I have a post-sermon conversation with my most recent ex. The situation is still tense, and then he tells me he is worried he might have cancer. He says he wants to get back together. Sometimes, I think it’s a good idea. In actuality, it’s probably a bad idea.

2 pm: Buy books on Christian ideals in dating. Start reading. I forgot those books usually condemn sex, am a little miffed.

8 pm: Go to concert with J. The concert isn’t bad, but J confuses me. He is so touchy in public but doesn’t cuddle or make out much in bed. We’re neck kissing in public. No one knows me here, so I don’t really care. When the concert ends, J offers to walk me to my car. A goodnight kiss? This is a new one. Usually, we are the awkward side-hug type.

10:45 pm: Back at home, settling in for a post-beer all-nighter. J texts me, wishing I was with him. I wait five minutes — an appropriate delay! — then text back something witty and make plans for later in the week. I fall asleep at keyboard again, around midnight. Must get a sleep schedule soon!


11 am: The Ex calls — he does not have cancer. We make plans to talk later about what we want out of a relationship.

3 pm: J texts. He’s persistent, if nothing else.

8 pm: Get to library, stake out table. Ignore texts from J, who wants me to go play “drinking games” with his buddies, who are married and circling 30.

2:30 am: Closed out the library and now I’m home, prepping for bed. Text from J. “Wish you were here.” I fall asleep watching “Gossip Girl.” Slept with my laptop again.


3 pm: J texts me Royals baseball trivia, obviously an opener to “when can I have sex with you?” We make plans to go out, even though I’m exhausted. I get a blue manicure in celebration of impending sex. It’s been three weeks! Clean entire apartment from top to bottom.

12:50 am: After we hang out a bar all night, J wants me to come over, but I convince him to go back to my place instead. Thrilled to discover my roommates are asleep, I plan to have loud sex. An hour later, though, J is too drunk to finish. Still does not cuddle.


5:45 am: Wake up to awkward, from behind dry humping. He already has no pants on and is “good to go.” Pillow talk quickly evolves into sex. Why do guys think groaning is sexy? Can I put a sock in his mouth? In 10 minutes the whole thing is over. Well, that was fast. Again, he does not cuddle.

8 am: Stumble out of my room after waking up, for real this time. When J and I go to leave, we run into my roommate. I am not amused. I drop J off at his house, awkward hug. Manage to back out into traffic without killing self, others.

TOTAL (if you’re counting): Sex twice with J, a bad make-out and awkward second-base groping with the photographer, ex-tension, and one emotionally ambiguous cuddle fest.

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