An Open Letter to My Latest Date, Part II

At least your apartment was clean; I’ll give you that. I’m not a fan of going back to guys’ apartments. I’d much rather bring a guy back to my place and be in my own environment (read: control freak) than risk the unknown (and likely visible pubes in the bathroom) in his.

I’d dressed up for our date and asked if you had a T-shirt I could sleep in. The first one you handed me, a shiny athletic shirt that was probably 100% polyester and would make me sweat all night, was so tiny it wouldn’t even fit over my boobs.

“Don’t you have anything bigger?” I asked, both mortified and annoyed.

You pulled out another shiny shirt, also doll-sized. I knew it wasn’t going to fit and didn’t want the indignity of even trying this one on.

“Are you serious? You don’t have a big T-shirt or anything?”

Here a new lesson was learned: Ladies, never go home with a man so skinny he won’t own one shirt that will fit you.

“Wait,” you said, “I know!” As though a proverbial light bulb had gone off.

You reached into a bag of laundry and pulled out a big, gray hoodie.

“Is that laundry clean?”

You assured me it was and said that the sweatshirt belonged to your friend.

I pulled on the hoodie, which was soft and fleecy inside, and you took off your shirt.

I feel horrible saying this – even now – but my first thought was that topless, you looked like Mr. Burns from “The Simpsons.” How could someone that skinny have that paunch?

You’d mentioned something at dinner about getting a beer belly, and I was like, “What are you talking about?” You probably weighed 130 pounds, tops. But it was true – your beer belly was just well concealed beneath your “GREAT MINDS DRINK TOGETHER” T-shirt and unappealing brown and cream hipster jacket.

We lay down on your bed, me in the hoodie and you in your boxers, and it was clear we weren’t just going to go to sleep.

I still didn’t want to have sex with you – and not because of your Mr. Burns-esque physique, but because it was our first date.

You crawled under the sheets and between my legs. It was great, except that you sounded like you couldn’t breathe. I’ve never had a man sound like he was suffocating in my vagina before, and it’s certainly distracting.

You stopped before I came, but I couldn’t blame you what with the way you were gasping for air.

“You need to learn to breathe at the same time,” I said.

You wanted me to give you head. I didn’t want to, but it was harder to say no after you’d gone down on me. I am not a fan of tit-for-tat sexuality, yet somehow I felt coerced into reciprocating.

This was when I first actually saw your penis, and it was tiny. Not microscopic tiny, but let’s just say if it were a cocktail wiener served to me in a bun at a party, I’d still be hungry after.

But I obliged, at least for a few minutes. Sucking a tiny penis is not an activity that I would ever actually enjoy, but I didn’t want to be selfish.

When I stopped, you wanted to have sex. I didn’t see any point and hadn’t wanted to in the first place, yet somehow I still let you nag me into it.

The sex itself was over almost as fast as it had begun.

When you came and started to pull out, all I could think was, “Really?

What had I expected?

“The condom came off,” you said.

What? Jesus.

If only I’d know this was a recurring theme on your dates. You didn’t even offer to take me to get Plan B.

Despite practically everything going wrong that could, I fell asleep easily, to my surprise. It was 4:30 in the morning after all.

You were a cuddly sleeper, which I like. Every time I changed position during the night, you changed position to keep holding me.

If only you were as good at sex as you were at cuddling.

The light leaking in through your blinds woke me up three hours later.

While I was still in bed, half asleep, you got up and left.

When you returned, you had half and half from Trader Joe’s as promised, and you even brought me coffee in bed. Then you got back into bed next to me and put your arm around me while I drank my coffee, with half and half and sugar just the way I like it.

So you actually were a nice guy after all.

Who cares about your tiny dick?

Ok, ok, I’ll be the first to admit I do care. But I was willing to give you another try. It was late the night before, you were tired, and you said it had been a while.

You had to leave soon because your friends were coming to pick you up to take you for a day in Los Olivos to celebrate your recent birthday.

Considering we’d already had short sex in which the condom slipped off, I really had nothing left to lose by giving you another try.

I lay on my side but it seemed like you were having trouble getting it in. Not only was your dick small, but it had a bend in it. You were tiny and bendy.

I turned onto my back, the same way we’d had sex just a few hours before.

You still seemed to be having a problem.

“Why won’t it go in no matter what position I get in?” I asked.

“It is in,” you said.

In all my years and all my sexual experiences, that is the very fist time that has ever actually happened to me.

What could I possibly say after that?

Your dick wasn’t just tiny and bendy, it was invisible, too. I literally couldn’t tell it was there.

Again, you came in under three minutes.

But what did it really matter? Even if you had gone on forever, I wouldn’t have felt anything.

Yet somehow, against all logic, I still liked you. The coffee and the cuddling had gone a long way. When was the last time a guy brought me coffee in bed? I couldn’t even remember. I was always the one waiting on the guy, bringing him coffee in the morning and wine at night.

I still wanted you to come make me chicken curry masala on Wednesday, tiny penis be damned.

You’d come through on the half and half, so you could be trusted. Right?

And there was the $100 you’d given me as collateral, to insure your appearance on Wednesday.

In being swept up on a sea of sweet, creamy caffeine, I neglected to mention that while I was having my coffee and you were cuddling me, you asked if I could give you $40 from the $100 you’d given me at the pool hall.

“I don’t have any cash,” you said, “and don’t want to go out to Los Olivos with my friends without any cash on me.”

“No,” I said reflexively. “I’m keeping it til I see you on Wednesday, like you promised.”

I was laughing and so were you.

But just like to get me to have sex the night before, you kept nagging me.

“Just give me back $40,” you said. “You can keep $60.”

You were being serious.

And what kind of asshole would I be to refuse to give you back any of your own money, when you’d gone out and bought me half and half when the store opened at 8 am and made me coffee and brought it to me in bed, and were going to cook me dinner in a few days?

“Ok,” I sighed. “You can have $40. In fact, you can have all your money back. You’re a nice guy.”

“I told you I do what I say,” you said.

I reached into my wallet and handed you back the $100 you’d been so anxious to hand off to me just hours before.

“But I’m keeping the sweatshirt until I see you Wednesday,” I said.

As I walked out, I realized I’d left my prescription sunglasses at home the night before, since I didn’t think there was any chance I wouldn’t be coming home. So I had to drive all the way from Manhattan Beach to Santa Monica without my sunglasses, and on three hours sleep.

I texted you when I got home like you asked me to. You responded immediately:

I had an awesome time last night.

I wrote back saying I had a great time too and telling you what a sweet guy you are.

You responded with a happy face emoji.

That was the last time I ever heard from you.

I was a fool to believe anything you said, to go back with you to your apartment, to let you nag me into sex, to be too easily charmed by too little effort, to have such a low bar for male behavior that basic keeping your word seemed charmingly chivalrous, and most of all, to believe what you said to me when all you wanted was to get into my pants.

Clearly, I should have kept the $100.

At least I got the hoodie. It fits perfectly.

This Post Has 20 Comments

    1. Sadly, Rebecca, it wasn’t even a damn good cup of coffee. It was just a decent cup of coffee. If only he’d been a decent guy.

  1. OMG, the invisible penis and sweatshirt slogan is too much and literally had me laughing out loud. It is hard to believe these men exist. I guess I need to appreciate my husband more, despite the occasional frustrations!

  2. Wow….Lisa…I..I have so much to say… And to ask..
    Now I’m hoping that this is some awesomely funny self-deprecating, fiction, as opposed to the living purgatory you seem to be dragging yourself through bi-weekly or monthly or however often you write this blog.
    I think I read the sentence… I didn’t intend to…. and the phrase… But I felt I had to reciprocate… at least 6 times in this piece
    To be clear I love you reading your blog. The entries you share are always insightful and well-thought-out.
    But let’s just say it seems that these retards you seem to be dating wherever you live have set the bar so low you’ve just become accustomed to capitulating in hopes of striking oil.
    Stop putting out until you either find yourself in the situation that the sex is worth humiliating yourself over or he’s so wonderful and goes down on you on the first date and live with wondering if he’s inside you or not.
    All said with love Lisa.

    1. Thanks for your concern, John. I don’t think sex is *ever* worth humiliating yourself over, but I do agree with much of what you said. Not being a woman yourself, you may not realize to what degree girls are socialized from early childhood to “be nice” and please men. This is why in self-defense for women classes they teach about the “internal attacker” that often makes women freeze when men are violating their sexual boundaries. Even assertive, feminist, grown women like myself may find ourselves rationalizing reciprocating when really we should be running for the door. Sex should never be about capitulating.

      1. Also, women need to really listen to those “little red flag” warnings they get throughout a date, and feel free to ditch the guy before it even becomes a sexual situation.

        “Giving him a chance” is one thing, but women needn’t ignore or accept obnoxious comments and inappropriate behavior to begin with. It’s definitely OK to say, “See ya!” after that first drink. Then go home and watch Netflix and chill with a glass of wine — by yourself. 🙂

      2. Totally agree. This creates an annoying situation in which women have to be extremely careful about the boundaries they set and how they communicate those boundaries. Specifically, if you tell a guy you aren’t going home with him, then you do, he’ll often conclude that your boundaries are negotiable and will attempt to get you to agree to the next thing he wants, usually sex (to be clear, this is not acceptable behavior on the guy’s part, but that doesn’t mean it isn’t super common).

        Social psychologists even have a name for this: The Foot In The Door Phenomenon. Basically it states that people are more likely to agree to a larger concession after having previously agreed to a smaller one. Rather than leading with “let’s have sex” a guy might start (as this one did) by saying “let’s go back to my place to hang out/have another drink/sleep/whatever”. Because you previously told him you didn’t want to go, changing your mind signals to him that you’re persuadable, which prompts him to launch into the next stage of his attempt to get you to do what he wants. I don’t think this is a conscious thing for most guys, but unfortunately telling him “no” and not sticking to it sets a bad precedent (it’s very different once you’re in a relationship, but when you’re first getting to know someone it’s helpful to clearly establish that what you say re: boundaries carries weight, and you’re not going to do things you aren’t comfortable with or interested in just because he whines/begs/bribes etc).

        In my experience the only way to avoid this situation is to not comment on whether or not you’ll go home with him until you’ve made up your mind. If he asks and you aren’t sure, be noncommittal; say “we’ll see” or something to that effect and change the subject until you’re ready to decide. I definitely don’t agree with “rules” about not having sex on the first date — I think you can and should if you want to. Just don’t let yourself be talked into it. Obvious exception to this is if you enjoy playing reluctance and being persuaded, but in that case you need to have a conversation ahead of time so you both know you’re role playing. Under normal circumstances, if you’re feeling indecisive about going home with him, you probably aren’t all that interested and it’s better not to bother.

        1. Thank you for the insightful and helpful comment, M! I actually did not know about The Foot in the Door Phenomenon, but I certainly demonstrated it in this situation, proving that my boundaries were fungible. I like your attitude and your suggestions. You are absolutely right that it’s better to be noncommittal than to say you won’t do something and then later do it. I am going to keep this in mind on all future dates.

          1. Glad to hear it, Lisa! Learning about Foot in the Door was a revelation for me as well – once you know what to look for you start seeing it EVERYWHERE.

  3. The tendency to give someone a chance is rampant, not just with first or second dates. Red flags are rampant as well, only we tend to ignore them thinking the person or situation will change after . . .
    Pay attention daily and speak up!

  4. People who romanticize the single-but-looking life don’t remember how annoying it can be. It takes superhuman resiliency. Good luck out there, Lisa.

    1. Thanks, Jenelle! Since the single-but-looking life does take superhuman resiliency, as you pointed out, maybe there should be a new superhero (or should I say shero?), Dating Woman. New meme, stat!

  5. I have a theory. Maybe these dudes you spark with have poor impulse control, as well? (Not saying you do, but if you have a hard time sticking to your own rules, then maybe?) I think when two people like this meet, it can be electric. It makes for a very fun time, because you both are being spontaneous and going with the first thing that comes to mind. That said, I don’t think it’s a good fit in the long run, because it can burn itself out rather quickly. Not sure what the solution would be. Maybe give the “meh” guys a chance? If they are promising on paper, give ’em two or three dates at least if they get in touch and seem honest? Give ’em a chance to let their guard down and show their personality, while at the same time giving the “sparky” guys a handful of dates to prove their trustworthiness?

    1. Interesting theory, Fontina. While Rebecca has a point that there are not a ton of “promising on paper” guys just floating around the dating pool, I did, in fact, have a date with one recently. We met for drinks and had no connection whatsoever. There were lots of long pauses in the convo, unusual for a chatty girl like me, but he’d actually written in his profile that he likes when the woman allows the awkward pauses in the conversation, so I repeatedly forced myself to sit in silence for 20 seconds, waiting for him to say something else. (Yes, I actually counted the seconds.) A first date like this creates no interest on either side to continue on to date two or more. And how boring would it be for you to read stories about three dates with a “meh” guy? I don’t foresee that being a popular series. 😉 I do think there has to be at least a tiny spark for either person to want there to be a date two, but yes, there has to be a middle ground between no spark and instant burnout.

      1. Agreed that you cannot manufacture chemistry. I think what may be the larger issue is recognizing the “asshole” right away in the potential burn-out guys (or any guys). If an early comment or conversation (such as this guy’s age diss, or his really inappropriate condom story) makes you uncomfortable, then maybe this guy is showing you who he is, and you should just say goodbye before it even gets to the point of making a sexual decision.

        Instead of dismissing the signs of dickishness, embrace them, accept them, and get up and go home. In this case, at least from what has been described in these posts, it seemed fairly obvious early on that this person was a bit of an asshole/pretty disrespectful. This was proven 100% AFTER the bad sex. Next time, the bad sex needn’t even happen.

        It can be tough, I know, if you want to give someone a chance. But if you’re getting bad feelings right away, listen to your instincts and tell the guy it’s time to end the date. If things start off in that manner (especially since “good behavior” is supposed to be the rule on date one), they are probably unlikely to get better.

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