It’s Too Soon To Break Up, But Too Late To Make A Clean Exit

A dating conundrum.

It’s Monday and I have a date today.

Technically, it’s my second real date with a guy I’ve had sex with, twice. Ray and I had a great first date and he’s swung by my place a few times for “a quick kiss” between meetings. While he gets the job done, I don’t particularly like having sex with him but I figure, that’s a teachable thing…right?

Ray is my rebound from my relationship with Jeremy, a guy I dated blissfully for nine months, and out of nowhere, he ended things. Every week, Jeremy breaks No Contact and reaches out with breadcrumbs. My brain tells me I need to survive the next seven days and if he reaches out again, I’ve got a message planned telling him to stop reaching out to me.

The way I figure it, the first stage of dating is fair game. Everyone’s dating multiple people until someone plants the flag of commitment. It’s only been two weeks with Ray but homeboy is smitten.

I know this because he repeats “Hey, I like you”. He tells me how different I am from Southern California women because I’m smart and can hold a conversation.

I’m not looking forward to this second date. That was my MO before Jeremy; begrudgingly getting ready for dates and driving home resenting my choice to date. With Jeremy, I was excited to get ready to see him and I was on cloud nine when I left.

But I need to give Ray a fair shot, so I vow to make an effort. I look at the self-tanner bottle on my bathroom counter. I’m half Indian, which means I look sickly if I’m not tanned but I avoid the sun like the plague. It’s a pain because there’s standing around drying time and showering off.

Eff that. The guy seems to think I’m hot as-is. I look at the bottle of hair dye on the counter. My divorce caused a few grays which kill my soul that screams I’m still only sixteen. It’s too late to apply now because I’ll reek of ammonia for the date.

At least I blow-dry my hair, get my makeup on, and find a dress. And then in true female form, I take it off and try on a few other dresses only to end up with the original fucking dress. It’s a light blue, short-sleeved fuzzy dress that clings to every curve. I pair it with baby pink heels.

This is my first time seeing Ray’s place and I try to keep an open mind. “Sorry, it’s still a mess from having the kids this weekend,” he tells me. As we walk to his car, I learn that he’s renting. In my experience, it’s a red flag if the guy is dating a relatively crummy-looking place. Not because I expect to date a millionaire but I’m not in a position to be anyone’s sugar mama like I was with Thomas, who made half my salary.

As we drive to the restaurant by the ocean, I glance at Ray. He’s a good-looking guy. Imagine Jake Gyllenhaal but with a longer chin and less hair. Ray constantly looks at me, saying nothing.

The guy does that all night. It’s creepy. It bugs me. I can’t help but say, “What?” when he looks at me in silence. “I can’t just look at you?” he replies.

No dude. Stop being weird.

Everything by the beach is a paid parking lot. As we get out of his car (the smaller version of my SUV, which makes me feel like I have a bigger dick), I see there’s some white stuff on the bottom of his jeans. Like someone threw white paint on them. I bite my tongue from saying anything.

As we walk, I struggle to pay attention to Ray. There’s something about the cadence of his speech combined with the boring content that shuts my brain off. I notice he takes any opportunity to brag. When talking about my current company’s shitty purchasing habits, he interrupts to say “You know I’m also an accountant, right?”

Uh, no. Also, I don’t care. What does that have to do with me talking about how it took me two months to get a $60 software approved?

Walking along the road, I notice that Ray doesn’t switch sides with me so that he’s on the side closest to the cars. Even my high school boyfriend knew the silent rule of being a gentleman. My brain flashes to Jeremy, who always moved me away from both cars and large dogs.

Instead of going to the planned restaurant, we pass by a popular spot and Ray decides we’re having dinner there instead. It’s packed and we’re at a small hightop against the wall. I look at the bar and long for the days when Jeremy and I beelined for sitting there because it always has a fun, upbeat vibe with everyone around.

Ray slides in throughout the evening about how we’re going to get naked later. He makes it sound like I’m the one who wants him and I can’t take my hands off of him. That’s what I get for having sex too soon.

It begins to irritate me how much Ray likes to tease me. I long for the days when I teased Jeremy, who said he liked it because “It keeps my ego in check”. They’re not cute, flirty teases. He interrupts me to make snarky comments and when I pause (because I’m annoyed he interrupted), he says “I’m just kidding!”

Ugh. If you have to repeat that you’re kidding, you’re doing teasing all wrong. I play the classy female by putting my hand on his arm and say, “You never have to tell me you’re kidding. I always know you are. I’ll never assume that what you’re saying to me is to purposely be mean. I know it’s a joke.”

I have never chugged a glass of wine so fast in my life. I need to get a solid buzz to survive this.

We continue chatting and I ask random get-to-know-you questions like food aversions and unpopular opinions. Ray asks the same in return but every time I answer, he attempts wisecracks. Listen bro, I’m the mother-effing queen of wisecracks. If the other person isn’t laughing hysterically and only gives a polite smile, you’re doing it wrong.

I tell the story about getting my green card and US Citizenship. I’ve told this story a thousand times, down to the funny parts or the topics people find interesting. As I talk about the quiz portion, Ray pipes in and asks, “Who was the sixteenth president?”

“Uh…I don’t know?” I reply. That wasn’t on the list of questions for citizenship. He practically yells the answer: Abraham Lincoln. I try to continue my story but he interrupts with, “How many of the original colonies were there?”

“I don’t know…fourteen?” I irritatingly reply. “Close, thirteen!” he answers and proceeds to list them off. As I type this up, I realize he sounds autistic but I assure you, he’s not (take it from someone who was diagnosed with autism and has a son on the spectrum).

Ray is arrogant. That’s a big red flag.

After dinner, we stop for gelato. I rush to pay for it because I want him to know I’m not a gold digger who expects the guy to drop cash on me. We walk to the beach while he tells me all the ways his ex-wife is a hot mess. Ray says that when his kids are older, he’ll tell them the truth about their mother’s bad behavior leading up to the divorce.

I try telling him that studies show even adult children are negatively impacted by divorce if parents smack talk each other. It makes them feel like they’re in the middle. Someone can be a shitty spouse but still be a great parent.

As Ray tells me he doesn’t care about the psychological toll it’ll be on his kids, I bite my tongue and simply say “To be clear, I’m not telling you how to parent. You have to do what you think is best for your kids.”

Oh, I’m totally telling him how to parent. This guy is parenting all wrong.

We walk back to his car and he makes a few more comments about how naked we’ll be in twenty minutes. Ray’s teasing about how badly I want him makes me want to claw my ears off. Women don’t want to talk about how much they want a guy. Women are turned on by hearing how much a guy wants them. I’m capable on my own of saying and demonstrating my eagerness without him announcing it every few minutes.

At the car, Ray kisses me passionately. I try my best to lean into it since he’s a good kisser. I’m trying. He opens the door and a sun hat I brought is laying on the seat. “Don’t forget your hat, I might want you to wear it during sex later,” he attempts to joke as he closes my door.

Time stops.

I think about how Jeremy keeps a hard hat and construction clothes in his truck for the times he visits job sites. I used to tell him I wanted him to fuck me in that uniform but we never did. The memory causes me to let out an audible gasp as I cover my mouth. Tears swell to my eyes and my body quivers in emotional pain.

When Ray opens his door, I slide on my sunglasses so he doesn’t see my tears.

We get back to his place and he immediately gets his Sexy Time on. He directs me to the bedroom.

Do you know what’s not sexy? A messy bedroom.

I get that life is hard with kids. But he hasn’t had his kids since the night before. And this is only his bedroom. I never make my bed but if I’m having a guy over, damn right my room’s going to dazzle like prom night.

He has a plastic Sterilite 3-drawer dresser next to his bed. I wouldn’t have noticed it except all the drawers are open with random things hanging off each one. His bed has blankets all bunched up. I can’t tell if I’m in a college kid’s room or if he’s been robbed.

Ray’s bedroom has a large closet with mirrored doors. As I watch him during sex, I tell my brain not to think of Jeremy’s mirrored doors and how good his reflection looked. Ray doesn’t have anywhere near the same physique. He also has a weird pattern when thrusting. Like it’s simple: in, out, in, out. He puts it in…then pushes a bit harder…then leaves it there…then pulls back…then pushes in deep…then pulls back…it’s all over the place.

I’m not sure why Ray’s dick keeps falling out despite it being on the larger side (no, I don’t have a large vag). Is it the angle of it compared to my vajayjay? I want this to be over but Ray’s ego is stroked by how often he can make me cum. Eventually, I start faking it.

I’ve learned that for Ray to finish, he needs a solid five minutes of barely any movement from inside while having his body smushed against mine. He held me on top of him while he moved his hips barely two millimeters. I had one hand over my head braced on the headboard. My right hand contorted itself behind me, rubbing his man meat as he slid in and out.

My arm is about to fall off. But Ray likes this new sex move I invented (don’t try it at home, it’s awful) and I need this night to end. Finally, he finishes. I think he wants to snuggle but I pull the oh-look-at-the-time-I-have-to-work-tomorrow move. He lets go of me after intensely staring into my eyes and repeating that he likes me.

After I get dressed, Ray gives me an affectionate hug and kiss. “So, I’ll see you again, right?” he says. From talks of our dating history, this is a guy who has no problems keeping women around. I nod my head in affirmation.

As I nod, my brain thinks “Aww hell nahh, this has to end”. I’ll figure out a way to end this before it’s already moving faster than I can handle. Plus, he’s intolerable between his bragging and interruptions.

I drive home, sobbing and missing Jeremy.

And then someone hits my car.

We were in the intersection driving straight, the guy tried getting in front of me but did it while he was right next to me. He barely spoke English and kept saying that he put on his signal. “I can’t see your signal if you’re next to me!” I yell.

I’m not confrontational. But my emotional state has zero effs to give. I yell at him to give me his insurance and registration. The guy refuses and tells me to call the police.

Geezus christ. I’m trying to find the local phone number since it seems the damage is cosmetic. After giving up, I call 911. The dispatcher tells me to pull into a restaurant parking lot nearby so we’re not blocking the road. Still, the guy won’t move and because his car is ahead of mine, that means I can’t move.

I call 911 again, which feels dumb because there are people actively getting murdered and here I am whining about this jackass who clipped my car. She tells me to hang tight and wait for the cop to arrive.

As we’re waiting, I call Ray and tell him that it’ll be a while before I send him a “got home safe” text. He immediately asks where I am. “No, no, I didn’t call you for you to come and help with this, I got it. I’m freezing but it’ll be fine the cops will be here soon.”

Ray tells me he’s coming regardless. It’s going to be one big party in the left lane of this street.

The cop arrives and directs us into a nearby parking lot. As he talks to the other guy, Ray arrives with a hoodie and a bottle of water. “I didn’t need you to be my white knight but it’s very sweet of you to do this.” I tell him, guilt-ridden that I want to cut him loose.

“Well, now you can see me in PJs and my glasses,” he responds, showing off his sweatshirt and shorts. He hugs me and repeats “It’s fine,” which is a catchphrase he often says, even during sex. Like dude, I know it’s okay. My car’s damage is minor compared to the other guy, I just refuse to pay to fix it when I didn’t do anything wrong.

When the cop has wrapped everything up and handed me paperwork for insurance, Ray kisses me and tells me to let him know that I got home safe.

Fuck. I can’t end this now, not when the guy knew the right thing to do was to show up instead of leaving a female wearing a dress out in the cold in the middle of the road at night. Ray was very, very sweet in that moment. There must be hoards of women who want a guy like him.

Now this means I have to have another date so that I don’t look like a dick ending things with a guy who immediately rushed out with a warm hoodie and hydration.

When I pull up in my driveway, I burst out crying. Everything feels upside down and not the way it’s supposed to be.

I just don’t know how to make it better.