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Diary of a Disillusioned Dater: Don’t be Disappointed

This is a true story…

I envisioned the emergency room surgeons desperately trying to remove my face from her gigantic ass cheeks

t finally happened – or did it? I’m not really sure. I’m still trying to figure out what exactly I did with Marty Applebaum’s niece.

About a half hour before I was going to leave my apartment tonight to meet Tammy, I noticed an email from dad that he had sent a few hours earlier. The subject was “Have a good time on your date.” The body read: “Don’t be disappointed.”

Don’t be disappointed? What the hell is that supposed to mean? I started to panic, and immediately called dad to find out what he meant, but mom picked up.

“Your father’s sleeping. It’s past eight-thirty. What’s wrong?”

“I’m supposed to meet Marty Applebaum’s niece in less than a half hour, and he sends me an email saying ‘don’t be disappointed.’ What’s that supposed to mean?”

“Why should it mean anything? He wants you to enjoy yourself. That’s all.”

“Then he should’ve said ‘enjoy yourself.’ Not ‘don’t be disappointed.’ Is there something you’re not telling me?”

“I wasn’t involved with this. I have no idea what he meant. Just go on the date. What’s the worst that could happen?”

“She could be two-hundred pounds.”

“Your father would never set you up with someone who was two-hundred pounds.”

Once again, mom was right. Dad would never set me up with someone who was two-hundred pounds – but he did set me up with someone who was two-hundred fifty pounds.

I sat across from Tammy in Starbucks, waiting for the hour I had allotted for this date to go by. After the general pleasantries about work, family, and how dad knows Marty, we had little to say to each other. I wasn’t really that interested in making an effort to keep the conversation going because Tammy was an absolute pig – both in terms of size and demeanor. She snapped at the kid who made our coffee for taking too long and she practically swallowed her Cinnamon Swirl whole.

I still felt an obligation to dad and Marty Applebaum to be nice to Tammy, so I tried to fill the dead air as best I could, but Tammy kept giving me one word answers to my questions. I was about to ask her about her shower routine when an old Chinese man walked by our table, and asked in a thick Chinese accent if the newspaper on the seat next to us was ours.

“Nee How,” I said to the man. “It’s all yours.”

“Nee How,” he said, smiling, as he took the paper and left.

“You speak Chinese?” Tammy asked, confused.

“Not really. But I’m taking classes,” I lied just to say something.

“Of all the languages you could learn, why waste your time on Chinese? Why not learn something useful like I don’t know – German, or something?”

“Because China is on its way to becoming the world’s largest economy. If you wanna take advantage of that, you need to speak the language.”

Her eyes lit up for a moment – like she hit the jackpot.

“So, like, you’re into finance and stuff?” she asked in such an excited tone that if she were a guy, she would have had a boner.

she asked in such an excited tone that if she were a guy, she would have had a boner.

“Not really. I just wanna be able to have an actual conversation with the Chinese guy I buy my bootleg DVDs from. I’ve been buying movies from him for over a year, and I’d like our relationship to move on to the next level. And somehow I don’t think he’s gonna learn English.”

Maybe I’m a really good actor, or maybe I don’t convey sarcasm well, but for some reason, she didn’t get it. I’m guessing it’s because she’s a moron.

“So, what – you’re into Chinese men?” she asked in a disgusted tone, her she-boner now subsiding.

“No. I just think it would be really cool to be able to speak Chinese.”

“I see,” she responded, disappointed that I wasn’t the rich international man of finance she was hoping to land – and we spent the rest of the hour quietly sipping our drinks.

I sat there wishing I actually did speak Chinese and that the Chinese man hadn’t left, so I could have someone to talk to. When the hour was up, we stepped out of the Starbucks together, and Tammy asked me if I’d mind walking her home. She said shedidn’t feel safe walking home alone at night, and I figured it was the least I could do for Marty Applebaum’s niece since I was never going to see her again.

We arrived at her building, and I was giving her the old “It was great to meet you, take care of yourself” routine, when all of a sudden she lunged at me. I thought she was going in for the cheek kiss, but our lips touched, and she thrust her tongue into my mouth. I pulled back, fearing for my life, but she lunged in again for a second attack. I saw her lips moving closer to mine in slow motion, and I felt trapped. I didn’t want to insult Tammy by pulling away a second time, but I didn’t want to lead her on either. I wondered why this couldn’t be happening with someone I actually liked, or was attracted to, when all of a sudden, I heardShmegs’ voice egging me on: “First get laid. Then meet someone you like. It’s been a year.” I looked at Tammy – all two-hundred-fifty pounds of her – and wondered how bad it would be if I listened to Shmegs. Maybe I’d be in for the ride of my life. Maybe Iwouldn’t be disappointed at all. Before I could decide what I wanted to do, she made the decision for me. Tammy’s tongue was in my mouth again, and her hand was down my pants.

I followed her up the stairs to her second floor walk-up. As she struggled to lug her oversized body up each step, I feared she’d fall back and crush me. I envisioned the emergency room surgeons desperately trying to remove my face from her gigantic ass cheeks, while mom watched in horror, as I gasped for each breath.

“You think he’s disappointed now?!” I could hear her crying to dad. “Breathe, Ray. Breathe!”

When we got to Tammy’s apartment, she grabbed my hand and led me to her bedroom. After more than a year of celibacy and numerous failed dates, I was seconds away from fucking MartyApplebaum’s fat niece.

“Get naked,” she ordered.

As I took off my clothes and watched Tammy take off hers, I was both excited at the thought of actually having sex, and repulsed by the sight of Tammy naked. The only thing preventing her gargantuan, drooping breasts from touching the ground was her Buddha like belly, which was likely the only thing preventing me from finishing before we even began. I stood there completely naked and completely erect, feeling weird, even ashamed, that anything in the room was turning me on. I worried that Tammy might confuse my raging hard-on with a desire to want to be her boyfriend when all I wanted to do was bust a nut in something other than a tissue. I feared having to go with her to MartyApplebaum’s retirement party, or to her niece’s graduation, or to some family wedding all because of what I was about to do. I felt guilty that I was using her just to satisfy an urge, and even guiltier that I wasn’t the least bit attracted to her, despite my boner’s insistence to the contrary. I was bothered by the fact that Icouldn’t just take care of business and worry about the consequences later like most other guys. I wondered why I was sogoddamn impossible, when I heard Uncle Jerry’s voice telling me, “You’re impossible because no one is good enough for you” – but I knew Tammy certainly wasn’t. She wasn’t attractive, interesting, intelligent, or nice, but then I remembered that she seduced me, and I used that to soldier through. If there were to be any hurt feelings on her part, they were of her own doing. I was just trying to be a nice guy by walking her home. I had no idea she used the “I’m afraid to walk home alone” line to get guys to fuck her.

As she pulled me into her bed and on top of her, I felt like a bear cub nestled in its mother’s bosom.

“Wait,” I said, stopping her before she could pull me in all the way. “Do you have condoms?”

She reached over to her nightstand and opened the drawer to reveal what looked like at least thirty female condoms. She grabbed one out of the drawer and ripped it open with her teeth like a fat, horny lioness tearing into a carcass to feed her young. I was surprised she didn’t growl as she handed me the wrapper and proceeded to insert the contraceptive.

“I’ve never seen one of these before,” I said, studying the insertion instructions on the packaging – more to avoid watching her put it in than to actually learn how.

“Okay. It’s in,” she said.

“In where?”

“In me!” she screamed, impatiently. “Stick your cock in.”

I tried to oblige, but I couldn’t find anywhere to stick anything in. Granted, it had been a while, but could I have possibly forgotten how to screw? Tammy noticed my look of confusion.

“Are you a virgin?” she asked.

“No!” I said defiantly, like a five-year old who’s been asked if he was a baby.

“Then fuck me already!”

“I’m not wearing my glasses. I’m having trouble – ”

“Gimme a break,” she sighed – and an image of Nell Carter popped into my head, which didn’t help matters.

She was losing her patience and I was losing my wood. Then suddenly, from in between the thigh and belly fat emerged what looked like a plastic bag with a ring around the opening.

“Stick it in there?” I asked, pointing.

“Yes!” she moaned – and I did.

I pumped away at that plastic bag for twenty minutes with my eyes closed, trying my best to think of someone else besides the behemoth from whose vagina the bag was protruding. I wasn’t sure if I was inside her at all, or if only the Glad Bag was on the receiving end of the pounding. When she screamed, “Cum with me!” I started frantically flipping through my mental rolodex of images of women so that I could blow my wad and be done, but nothing was working. The guilt, disgust, and severe back pain I was feeling prevented me from experiencing anything remotely ejaculatory.

“I’m cumming,” I said, giving her my best cross-eyed orgasm look.

“Me too!” she moaned, as she pulled me in even closer.

My face was now buried in a pool of her breast sweat while she continued to moan, and I almost cried. When it was finally over, she released me from her bear hug. I pulled out of the Ziploc and quickly scanned the room for my clothes, so I could get dressed, go home, and bathe for a week. But then the guilt set in once again. I couldn’t leave this sad, lonely, overweight woman alone after I’d just violated her. It was clear she had sex with men so quickly after meeting them as a way to prevent them from rejecting her. She obviously didn’t want to be alone. Though I could totally relate to her desire for companionship, I was dreading the thought of having to lie next to her for the remainder of the night, possibly even having to cuddle, when I head her say, “You should go.”

“Excuse me?” I asked, not sure I heard her correctly.

“It’s late. I have work in the morning,” she said.

What I should have seen as a gift from god – the ultimate get out jail free card – actually insulted me. I was worried about violating her and hurting her feelings, when she was the one who violated me, and hurt my feelings. She basically used me as a human dildo, and was now kicking me out into the street, feeling completely used and entirely unsatisfied. Was this what dad meant by “don’t be disappointed?” Did he know she did this to guys? Did Marty Applebaum tell Norman that his fat niece fucked guys on the first date and then sent them packing?

I got dressed and watched Tammy pull the sheets over herself, as if she was suddenly embarrassed to be naked around me. For a moment I knew how Jonah must have felt. Tammy had completely taken away my upper hand. I was the one who was supposed to be rejecting her.

“We’ll talk,” she said, as I put my shoes on and walked out of her bedroom.

“Yeah, say hi to Marty for me,” I shouted back, as I closed her apartment door behind me.

I walked the thirty blocks home in a state of bewilderment. This was the “walk of shame” to end all walks of shame. I thought about stopping and asking a man I saw hailing a cab on Columbus Avenue if screwing a plastic bag without cumming actually counted as sex. I envisioned him answering, “You must have just fucked Tammy. Welcome to the club.”

I considered calling Shmegs to tell him what had happened, or responding to dad’s email, but I’m too embarrassed. Helen and Norman will definitely be hearing about the Starbucks portion of our date, but the rest of the story I’ll have to take with me to the grave.

At this moment, I’m no closer to meeting “the one” than I was when I first asked Shmegs to set me up with Linda. I’ve been rejected, humiliated, disillusioned, and now molested. I had hoped that by now I’d have had a romance that lasted more than three dates – or at least had intercourse with something not made of polyurethane.

Tonight, in my most recent moment of weakness, I logged back on to Jdate, hoping to find some fresh faces. I thought bathing in the cesspool of Jdate would wash away the shame I felt from fucking Tammy that my forty-five minute shower couldn’t. But I found the profiles of the exact same women who ignored me when I was a paying member.

I was actually pleased to see these Jdate Superstars still just as hopeless as I was waiting for their Jdate princes. I took solace in the fact that they hadn’t yet found the men of their dreams, and it wasn’t just me they were rejecting. I scrolled through a dozen pages of pictures I’d seen only weeks earlier, and somehow despite their forced smiles for the cameras, they seemed sad and defeated. I wondered if the men they were writing to were ignoring them like they did me. What once looked like The Hadassah catalogue now looked more like an online version of “Auto Trader” magazine. These women looked used – or certified pre-owned at best. They’d been around the block more than a few times, and the long numbers after their user names might as well have been a listing of the mileage they’d accrued.

When I read one woman insisting in her “About Me” section that: “I’m not into the drug scene! If it’s not legal, it’s a drug. Don’t try and tell me otherwise. Just keep moving!” I imagined the baggage she was carrying around with her from her ex-boyfriend the pothead, and I kept moving – right off the site.

I even logged on to to see if they were still overstocked with women, but their excess inventory looked scarily like what Jdate had to offer – despondent and discouraged women with poorly written profiles. I thought about signing up for Match’s free trial and emailing the woman whose entire profile consisted of the phrase “I like dogs, shopping and Bingo.” I was going to write her that I knew of a fixed Bingo game at a retirement home I could take her to, and that we could go dog shopping with our winnings. I then remembered that she ignored me when I emailed that to her on Jdate.

I officially have no prospects and no hope.


This article was generously contributed by diaryofadisillusioneddater. Check the blog out for more!

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