Encounter #76.1: Navy

App: Tinder

Name: Kurt*

Date Location: Dovetail – Charlestown, MA

Location Review:  4.5 Stars – Drinks were great. Food was tasty. Would 1000% go back.

Date Duration: 6 hours

What Happened:

Kurt appeared to be cute in his profile and was someone who not only could keep a conversation going on the app but, he kept it interesting. He asked unique questions and it seemed like he truly wanted to get a sense of who I was, my values, and what I was looking for. Not bad.

He gave me a date and place to meet and when I saw the menu I was pretty excited. I don’t normally drive down to Boston during the week but for that menu, I could make an exception. He beat me to the restaurant and as I approached him it looked like he put some real effort into his appearance that day. My dude had a fitted button down, nice pants, whole thing.

Overall Kurt was really kind. He grew up with a single mom and very much respected women because of that. He had an interesting history and it was clear he really had to bust his ass to get where he is now. He used to do video editing for a local college back in Denver but with COVID had to shift gears and decided to join the Navy.

Despite that, there was just something off. I didn’t know if he was just an awkward person or if it was because he was from the midwest but it just wasn’t working for me. He also had an interesting dating history in that he didn’t have any whatsoever and he did tell me that he was a virgin. Nothing wrong with that but, just not something I am looking to jump into.

He walked me to my car at the end of the night and we hugged good bye. Because he was so nice I felt like I should text him rather than ghost. I said my piece, let him down easy, and that was the end of that.

Encounter #74.2: Deez Nuts

App: Tinder

Name: Peter*

Date Location: The Hidden Pig – Haverhill, MA

Location Review:  4.0 Stars – The dry rub wings? Fucking magic.

Date Duration: 6 hours

What Happened:

I was dead inside. Peter was there. He offered to take me out for food. I said yes. I met him at his place and we had some time to kill before our reservation. So we ended up making out very aggressively, me blowing him, and him finishing on my chest…I had been there 10 minutes.

After some clean up, we drove over to the restaurant together. Despite us having different values, he was extremely easy to talk to. There was never any awkward silence and genuinely, I did enjoy talking to him so dinner went fine.

When we got back to his place we cuddled up on the couch and watched some Netflix. I did notice though that he’d ask for my opinion and then completely disregard it. He asked me what I wanted to watch and before we settled on Netflix I saw a tile for South Park. That was shot down. We got to Netflix and he asked me again and I saw something that looked good. That was also shot down. Bro, why bother even asking me my opinion if you’re just going to do whatever the fuck you want anyways?

We settled on Sex/Life and watched a few episodes. Then he asked me if I wanted to continue what we were doing earlier upstairs. Fuck it.

It was uhhh not great. At first things were fine. He was doing stuff to me but the issue was that it lasted about 2 minutes. We were upstairs maybe 5 minutes and he already reached for a condom. I asked for more and he just kinda rubbed my clit for a sec and that was it. We started fucking and it just wasn’t all that great because quite frankly it was entirely about him and his ego. Since he blew a massive load earlier, he wasn’t having luck finishing so he asked if I’d lick his balls again.

Hoping that last time was a fluke, I agreed. A few minutes in it started. “You like deez nuts?”. I dried up instantly. There was a moment when I was down there that I thought to myself, “Laura, if you end up dating and marrying this guy you’ll have to hear this for the rest of your life” and I couldn’t do it. It took everything in me not to bust out laughing.

I left not too long after and decided that that was the end of this run. I will say, for someone who claimed to be such a gentleman this fucker didn’t text me the day after we had sex. Actually he didn’t text me for a week until he asked at 8pm if I’d come over to Netflix and chill. Hard. Pass.

Encounter #74.1: Deez Nuts

App: Tinder

Name: Peter*

Date Location: Buono Bistro – North Andover, MA

Location Review:  4.0 Stars – So nice and very classy! Would absolutely go back to try some of the entrees. They looked amazing.

Date Duration: 6 hours

What Happened:

You know how when you’re hungry you shouldn’t go to the grocery store? Same idea applies to using dating apps when you’re lonely.

I swiped right on Peter during one of those nights where I just wasn’t feeling fantastic so when he messaged me and asked if I’d like to get dinner the next night I wasn’t expecting much. Tbh I didn’t even remember his profile so figured I’d just say “Fuck it” and go for the meal.

The restaurant he picked looked v nice so was excited at least for that part. When he got out of the car he was a bit more petite than I thought he’d be. Not unattractive but I had a solid 2 inches and 25 pounds on him. Fuck it. I was already there.

We got seated in a booth and he ordered a bottle of wine and an app for us to share off the bat. AIGHT. It didn’t take much for him to give me the life story. He worked in finance and recently bought a condo. Definitely had much more traditional views than me especially when it came to gender roles in a relationship. Politically he was a, “I think we need to come together…I didn’t like Trump as a person but fiscally he made more sense” types. So take that as you will.

He also was relatively fresh out of a relationship so that was a fun thing to hear about. Basically, he dated this 21 year old girl (he was 28), she felt that the relationship was moving too fast, and she freaked out. Totally get it. She was a baby and he was talking about her moving in and eventually getting married. Just different walks of life. He did mention though that he normally dates in that 21-23 range but then also didn’t understand why that wasn’t working out. K. You do you, Peter. But he did say that he was totally fine to start dating again and be out with me because he hadn’t thought about her all week. What a flex.

Now I can’t explain how the rest of this happened but all I can do is chalk it up to I felt dead inside and just wanted to see wtf would happen out of sheer boredom. If you’ve ever dated a lot, you may know this feeling all too well. You’re truly just numbed out and want to see if you can feel anything. Could be happiness could be disgust. Just want to see how dead you are. (Disclaimer: I go to therapy and shit regularly. It’s really fine).

Throughout the night, I did notice he was constantly staring at my tits. I mean I get it but be less obvious. He was also moving closer to me in the booth. We were talking love languages and I said mine was physical touch and he started holding my hand. This man had baby hands like I have never seen before. Wow. Truly a modern marvel.

Somehow we ended up making out in the booth and I was 50 shades of uncomfortable. I’ve waitressed before and this was a nice restaurant. I can guarantee our antics were gossiped about in the kitchen.

I suggested we continue this at my car. He paid the check and let himself into the car. I meant outside of it but okay. I guess we’re doing that. He kept insisting that I go back to his place and I agreed on the basis that we don’t fuck. Apparently that was fine and I went to the condo.

Place was decent. Little bare on the walls but for a man’s place not bad. He gave me the tour and as it always goes, when we made it to the bedroom started making out. I was still on my period so I didn’t get all too much out of it but when do I ever? I made moves to blow him and he asked me to lick his balls. Fine. I’m already down there and about to put a dick in my mouth. Doesn’t make too much of a difference. Then it happened.

He was more vocal in bed than I had been used to which wasn’t necessarily a problem. What I had issue with was what was said. After a few “Oh fucks” he came out with “You like these nuts?”…what? There was no way I heard that right so I just kept going and he said it again. And again. And he didn’t stop until I said “Yeah” which, by the way, is very difficult to say when you have someone’s balls in your mouth.

I was shocked so when he asked to finish on my face I really just kind of went with it. He really said “these nuts” in bed. This couldn’t have been real.

I left shortly after and for whatever reason, agreed to go out with him again.

Encounter #72.1: Mr. Brown

App: Tinder

Name: Stanley*

Date Location: River Bar – Somerville, MA

Location Review:  4 Stars – We just drank so not sure how it is food wise. Was close to a parking lot and faced water so that was really nice.

Date Duration: 4 hours

What Happened:

After the trauma of a date the night before, I needed a win. Stanley came off very high energy and fun based on his profile alone and looked like Sterling K. Brown so I was down for whatever. He asked me out for drinks and took the time to find a place with parking so that only got him extra points.

When he walked up, he looked just like his photos and really did look like Sterling. It was wild. I had just come from a baby shower so I was a bit more dressed up than usual. He gave me a hug and immediately went in with, “Damn, look at you! Baby isn’t even born yet and you already stunting on that kid.” I was sold. This was going to be a fun date.

Talking to Stanley was freaky easy. We both love to just shoot the shit so there weren’t any awkward pauses. From what I could tell, he had his shit relatively together. Because of COVID, he had to move back in with his family but he signed on a lease and was moving out by the end of the summer. Stanley went to Boston University and was also a former RA so we had plenty to talk about there and he also worked in marketing. Just endless things to cover.

We were there quite awhile and I wasn’t sure if he was into me or not. Yes, conversation was there but we’re both bullshit artists. Was he just talking to talk, or was there something more?

At one point he reached across the table and tapped my hand while he was talking. Okay, promising. I pushed my hand a little closer towards him and he took the bait. Hand was held. Houston, the ship has landed. Apparently we looked cute together because the waitress kept stopping by and going “Ugh, you guys are so beautiful!” and shit like that.

It was getting late so Stanley held my hand and walked me back to my car. I thought he was going to go for the kiss but instead we had an oddly long hug. When we broke apart he asked if he could kiss me. It was alright. I was coming off the Air Man from a few weeks earlier so in comparison, it just didn’t have that same magic.

We texted here and there in the weeks after but with it being summer, neither one of us was ever free and the spark died naturally.

Encounter #69.2: Air Force

App: Tinder

Name: Colton*

Date Location: Panera Bread

Location Review:  N/A

Date Duration: 5 hours

What Happened:

Since our first date, Colton and I talked nonstop. Also, things got a little saucier than they were before. Like we were writing each other erotica and having the “What do you like?” conversation. Despite us both being truly disgusting, it never crossed into a creepy or uncomfortable territory. Even though he said filthy shit, it was still respectful if that makes any sense at all.

The plan was I’d meet him on base and then we’d go and get brunch. Gotta be honest, the Air Force base in Massachusetts looks like a 1970s community college. I parked at the house and somehow I ended up inside. Within about 30 seconds we were making out, he picked me up, and carried me to the couch. Hot.

I was a bit hung over so even though the work he was putting down felt great, I needed to eat something. I pumped the brakes and we headed out to brunch.

Now I was told we were getting brunch in Boston. We ended up in Burlington, MA. Not bad, but it’s not Boston. A bit different. The restaurant he wanted to go to was nice but they didn’t do reservations and there was a 40 minute wait. Then we tried 2 more places and they were both closed. This left us with Panera Bread.

He insisted on paying for everything and made a point to be the one to go up and get the food and all that. Any opportunity he had he’d touch me in some way either by holding my hand or having some part of him touch me which I really liked.

Brunch was fine. I was hurting and he had a cross fit competition the day before so we were both a bit dead (more on that later). But once we got some food in us we started to get back to our normal baseline.

On the way home, he gave me a tour of the base and mentioned again that he was looking to leave it. After seeing everything, I didn’t blame him. But, it made it clear that this was probably just going to be a casual thing. It wasn’t ideal but, I also wasn’t opposed to having a little summer fling situation.

We got back to his house and as expected, things started happening upon arrival. He got my clothes off and went to work pretty quickly and it just wasn’t it. I won’t say it was bad but, it wasn’t my vibe. The moves he whipped out were something I’ve only seen in porn. He more or less spread my cooch apart and went in like it was a watermelon. Sir, there is only one spot I need you to work on and you’re everywhere but there. On top of that he was playing with my tits but not in a pleasurable way. It felt like he was trying to pull them off my body. Just no chill. Warm up the car a bit before getting in there.

I asked if I could reciprocate so I made my way to blow him. At this point in time he was completely soft. Okay, he’s the type of person who needs to be actively touched to get hard. That’s fine. I got to work and after about a minute he pulled my head up. I kept jacking him off and 30 seconds later I felt it. My hand was suddenly drenched and was incredibly warm.

I didn’t want him to feel weird or be embarrassed so I didn’t look down. I just kept making out with him and waited for him to say something. He sighed, apologized, and blamed it on being dead from his competition the day before. I mean it happens. I wasn’t going to make it weird. I get it. He wasn’t feeling 100, I was a new person, whatever. I was going to be there a few more hours anyways.

We spent the next few hours cuddled up naked on the couch making out. The conversation just wasn’t there though. I realized that since I got there that morning, he asked me maybe 3 questions and it was a lot of me carrying the team.

Eventually things heated back up again and got better on my end. Still not as good as promised but, it wasn’t horrible. I asked again if I could work on him. This time he lasted 2 minutes. I know my strengths and I know I’m good. I’m not that good though. This was a day for personal records.

We cuddled a little bit longer and then it was time for me to head out. He had to watch his sergeant’s kids and I was just tapped out. He walked me to my car but made no mention of future plans. We kissed and I went on my way. When I got home I sent the “Thank you for having me blah blah blah” text and to my surprise he responded and said he’d want to do it again. We texted here and there in the days after but it just wasn’t the same. He wasn’t nearly as talkative and it just felt forced. The only times he really asked me anything or seemed interested were when things got a little sexy.

I never answered his last text of “hahaha”, and that was the end of that.

Encounter #69.1: Air Force

App: Tinder

Name: Colton*

Date Location: Sully’s Ice Cream Stand – Chelmsford, MA

Location Review:  4 Stars – Ice cream was so good and was super thick and creamy. Is cash only but has an ATM.

Date Duration: 6 hours

What Happened:

Colton was a winner of “how hot can I bag”. I didn’t really know what to expect but he was good looking and double messaged me on a day I ran into an ex’s family member and was vulnerable. Bitch couldn’t resist.

Talking to him was oddly easy. We had very similar, dark senses of humor and just vibed. He grew up in North Carolina and then joined the Air Force as a medic so he had lived a bunch of places. Despite being military and originally from the south, he didn’t seem to have the belief system to match. He was very respectful of me though and would call me m’am over text which was so fucking hot. Colton was into cross fit and was ripped af so that was fun. Wasn’t mad about some of the pics I got leading up. Also he was reform Jew so that was on brand for me. Was bald though. Can’t have everything.

He wanted to meet my dog and go to a place where we could walk around for a bit so we decided on an ice cream spot that was halfway between the base and my place. He walked up to my car and he looked just as good as he did in his photos. That body don’t quit.

We got some ice cream and took our spot on a bench. Conversation flowed just as easily as it did over text. My dog was being a pain in the ass so we decided to walk around so she could calm down. There were a few times during the walk when I thought we were going to kiss. There was a moment where I saw a horse and I was trying to point out where it was and he just kept staring at me. Then we stopped to chit chat while I let my dog off leash and thought it was going to happen. Nothing. Finally, he went in for it and holy fuck it was perfect. Just the right amount of tongue, had his hand tangled up in my hair while the other was on my back, and the whole world felt like it stopped for a minute. Just magic.

We kept walking around holding hands. We had established early on in the texts prior that we were physical touch type of people so it felt easy in that aspect. No matter what someone was either holding a hand, touching a shoulder, or putting a hand on a back which felt so safe and nice. He was into me and the feeling was mutual.

While we were out he asked me out for another date a few days later so he could take me out to brunch. #Swoon The only possible red flag was that he was looking to transfer to a new base…in Arizona. I wasn’t sure if I had misheard him so I wasn’t going to make it weird.

Despite that, the whole night was just comfortable and very easy. We laughed a lot and made out in between jokes. Eventually my dog was pooped from running around and we decided to call it a night. After I threw her in the car he really went to work and holy fuck the man was good with his hands. Dear god. Basement was flooded.

It was exciting to just be excited about a person again. Even if it didn’t pan out, I was happy and just so curious to see what could happen next.