When I was around 17, my parents took the family on a trip to the east coast. At one of the resorts, after what was a long travel day, the rest of the family went to bed early. I was not interested in sleeping at 9pm, so I donned my board shorts and went to the resort pool to do laps.

About 10 minutes in, a girl around my age and her little brother got in the pool and kept to themselves, so I continued swimming past them as they splashed each other.

Another 10 minutes go by, while I was thinking of wrapping things up, two girls, both look to be around my age, slide into the pool. Both were extremely attractive--tall, slim, almost comically large chests, which, in bikinis was almost too much for my 17yo brain to process. Immediately after getting into the pool, they approached me to see if I want to play catch with a tennis ball.

Twist my arm...

I come to learn that the taller of the two, is also 17, and the shorter was her 12yo sister. Within 5 minutes of playing catch, the older one switched up the game; instead of catch, it was more of a monkey in the middle ball toss.

The original girl and her brother left the pool, probably annoyed by our game, which was getting raucous. Now a three-person game of monkey in the middle, the older girl began to make sure I had the ball while she was "in the middle", and aggressively tried to get it; not by intercepting it in the air, but by grabbing it. She would reach across me to get it, very intentionally rubbing her disproportionally large breasts on my body and face.

Let's be clear: I was perfectly content with this setup.

As I got more playful with keeping the ball from her, she got more even more aggressive; with one hand trying to get the ball, the other was actively groping, rubbing, grabbing, and squeezing my now extremely hard package.

By this point, was throbbing hard. I could barely think straight, and as if by ESP, the younger siste excused herself from the pool to go back to their room.

This left the older sister and I alone in the pool. She pulled me in as hard as she could, my pulsating cock pressing into her abdoment while we made out.

After about 15 minutes of pawing, grabbing, squeezing, and caressing, she literally grabbing my package as if it were a handle and effectively motioned to get out of the pool. We walked to a pretty dark part of the property, where she then took off her top, pulled down my swim trunks, and stroked me--and said something that I will NEVER EVER forget: "oh my god. You're like twice the size of my boyfriend". She wasted no time going down on me, giving me what was probably the best worst blowjob of my life, all while I felt her amazing body up.

I hate to say it--my life may have peaked that night.

And: For the record--I'm pretty sure she was exaggerating, because, if not, that poor poor guy...

While I was working retail, I met up with a match about a mile from my store. On paper, she was a good fit; attractive, well educated, and had a stable job as a children's therapist.

We enjoyed a delicious pizza and what was (and still is) one of my favorite pizzerias, though the conversation was...difficult. I tried to start a meaningful conversation, but either she wasn't having it, or she just plain ol' wasn't interested, and was looking for an out.

To avoid her needing to give me the boot, I settled the bill, prepared to give the, "Thanks for coming out, I'm not sure this is goign to work...", but she got there first, and said, "Let's take a walk! It's a beautiful night!"

So walk we did. We aimed towards where I worked, all the while, she droned on about whatever subject came to her mind. I don't know if it was the content, her voice, or my mood, but I was losing my patience rapidly. In an attempt to dodge the awkwardness of just cutting it all off, I surreptitiously texted one of my colleagues, and he called me. I apologized to the date, took the call, and my pal informed me he needed a ride to the next city over STAT.

She bought it, and I escaped.

It was the first and last time I pulled that trick, and I still feel bad for it.
 

Sometimes, I’ll find myself chatting with someone for months before meeting up, if we even meet at all. Such was the case with “Belle”. She sent me three very blurry photos of herself (one was actually a scan of her passport photo, so it had a hologram through it), and while that’s normally a red flag, she seemed very nice, and we talked on the phone a couple times a week. I continued to pressure her to meet, yet she always came up with an excuse why she couldn’t.

Finally, one afternoon, she IMed me and asked if I wanted to meet for lunch. I readily agreed, and met up with her at a nearby shopping area.  I was pretty excited, as we knew quite a bit about each other, and putting a non-blurry face to a person is fulfilling.  I had a picture of her in my mind, based on the photos, and from what she told me over time.  5’8″, a little “chunky” (her words”, and clumsy.

She walked up to me in the parking lot, and said hello.  I was stunned–she was gorgeous, had an amazing figure, and if she was clumsy, her heels didn’t indicate any clumsiness.  We walked to a nearby café and talked for a bit.  Something was a bit off–she was much more aggressive in her tone than she ever was on the phone, and something sounded…different.  “Belle,” I started, “tell me more about what you’re studying.”  She looked at me with a grimace.

“Adam, I wish you’d stop calling me Belle.  It’s creepy.”  I was confused.

“What do you mean?  Isn’t Belle your name?” I asked.

“No,” she said, “Belle is my little sister.  I’m Hailey.  You and I never chatted or talked before, but my sister talked all about you constantly–I wanted to see what the buzz was all about.”

I didn’t know what to say.  She had switched places with her sister!

“Adam, please don’t tell Belle that we met.  I didn’t tell her I was doing this.”

So we talked for a little bit longer, and then parted ways.  As it turned out, Hailey had just broken up with her  boyfriend, who she talked incessantly about, and apparently just needed someone to talk to.

About 6 months later, I met Belle.  She was, in fact, 5’8″, “chunky”, and clumsy.  In person, she wasn’t as open as she was on the phone, and it just didn’t work out.

Ok, maybe that wasn’t *that* exciting, but I figured it was worth sharing!

Interestingly enough, I haven’t had that many online dates lie to me about their age–and if they have, they’ve appeared to be awfully close to their actual age.  In the few times when someone has been older than the date listed on their profile, it’s usually no more than a year or two.

That said…what scares me the most is the prospect of meeting someone who has lied in the opposite direction…  This hasn’t happened in a long while, as my dating preference is really older than 24.  But when I was 19, I didn’t mind dating someone 18.

So I was 19 or 20 when I met “Jane” on one of the sites that doesn’t allow postings for people less than 18, which, at the time, wasn’t common.  Some sites would allow people as young as 16, which was probably for those states where the age of consent is lower.  We had been chatting for about a week, and I saw around 15 or 20 photos of her.  Cute, a killer smile, and a rather stunning figure led me to believe she wasn’t faking it.  She was a freshman at a local Orange County community college, and seemed to be pretty bright.  So I asked if she wanted to hang out one night.  She agreed, and I met up with her at a Starbucks near her house.

When I met her, something seemed a bit off–nothing too terribly alarming; though I was a little surprised that she had some slight B.O., and her style sense was a little bohemian.  She was wearing overalls and a ribbed long-sleeve shirt, which only served to amplify her appearance of a rather large chest.  There were no seats in the Starbucks, so she asked if we could hang at my school.  I agreed.  On the drive up, I noticed the B.O. a bit more, but the conversation was a little odd, too; she didn’t talk much about school, and was focused more on entertainment gossip.

We arrived at my school, and we decided to hang out in my dorm room.  I’ll admit that I was a bit excited, she was definitely very good looking, and what 19/20 year old guy doesn’t want that??  We talked about what television shows she watched, what music she listened to, what movies she liked…and she suddenly says, “So, do you like my outfit?”  I was a bit stunned by the sudden change in topic, but told her that she looked very nice.

“Very nice?” she asked, “Just nice?”  I know a complement fisher when I see one.

“Actually,” I said, “you look great.”  She seemed excited.

“I’m wearing a new top,” she started, “and a new bra.  It’s not padded, and to see?”  Through her shirt, she pulled the bottom part of her bra and squeezed it to show it wasn’t padded.  I was being pulled in two directions–I wanted so badly to reach out and feel what looked like legitimately huge breasts, but the alarm bells were piercing my thoughts.  I closed my eyes a moment, and took a breath.

“Um, Jane, look, I would love to do more–but something doesn’t feel right.  What did you say you’re studying in school?” I asked.

“Pre-calc, biology, AP History…” she started, and stopped short with a small gasp, before she said, “I mean…uh…”

For some reason, I wasn’t surprised, “So not in college, then? How old are you really?”

She stammered, “No, no, I meant World History…I’m 18.”

“May I see your ID, please?” I requested.

“No, I don’t have one,” she said, “I don’t need one because I don’t drive.”

I shook my head. “Sorry, everyone has an ID if they’re over 18–even if it’s not a drivers’ license.  I’m taking you home.”

So during the drive, she was begging and pleading to continue the date–all the while insisting she was 18.  Later on, after I got back to my dorm, she and I chatted a bit longer.  She admitted to being 16, and that she was sorry, and that she wanted to hang out again.  I responded by saying no, and blocking her.

This was a really close call; had I not been more cautious…well, let’s just say I’m glad I was.  Since then, two other people lied about their age, but both came clean from the moment we met, and fortunately, disaster was averted.

Surprisingly enough, people lie about obvious things.  In fact, as you’ll notice, that’s the cornerstone of bad online dating stories.  Usually it’s something small; she’ll say “I weight 120 lbs” when she really weighs 130lbs.  Not a big deal.  “I’m 5’6″”, she says, but she’s really 5’4″.  Not the end of the world.

Elisa, however decided to go full bore on the lying front.  After chatting online for a couple weeks, I determined that she was very nice, had a pleasant personality, and would be fun company.  She sent around ten photos of herself, and she fit her description to a tee: 5’8″, 130lbs, a very proportional body, half white-half asian of some kind (I really don’t remember at this point).  She had gorgeous green eyes, and dark brown hair.  I was excited to meet someone who fit my preferences both physically AND mentally.

The plan was to meet at the Sharper Image at a mall in the South Bay.  Sure, it was a 30 minute drive for a first meet, but hey, you can’t drive too far for potential love, right?  So I got to the Sharper Image a little early, and was browsing through their products.  (At the time, both Brookstone and Sharper Image actually sold cool stuff, not crappy plastic shit.)  While I was looking, one of their employees tapped me on the shoulder.  I turned to explain I was just looking, the woman said, “Adam?”

I looked at her, and said, “Hi, um, do I know you?”  She looked hurt.  “It’s me, Elisa!”  I was shocked…  If this was Elisa…then who was the girl in the photos?  The woman in front of me could not have been taller than five feet, and couldn’t have weighed less than 200 lbs.  My first thought was, if she fell down, she’d roll until she hit something that could stop her.

“You’re not what you described,” I started.  She acted like I slapped her across the face.

“Well, everyone lies about their appearance!” she hissed back, “it’s not my fault you were so dumb that you believed me.”

I started walking out of the store, and out of the mall.  She began to follow me.  “What, you don’t want to hang out?” she asked, trying to keep up.

I turned, and walked backwards for a moment, seeing her struggle to match my fast pace, “No, I don’t.  Relationships start with trust.  I can’t trust you if you lied about EVERYTHING,now, can I?”

She was falling behind, panting from the 30 feet of exertion, “You wouldn’t have agreed to meet up with me if I had told the truth!”

Before I spun back around, I said, “We’ll never know, will we?”  I walked back to my car, leaving her far behind to catch her breath.

I don’t even know what the moral of this story is.  Honestly, most people don’t lie as badly as Elisa did–and really, I don’t think most people have the guts to actually meet up after doing so.  Who knows.

One of the most important aspects about online dating (or really any first date, for that matter) is an escape plan.

During a holiday break, at the end of December, I found myself bored and restless.  What better way to spend one’s time than meet someone new?  Well, I was underaged, so a bar was not an option; I went online and got “double matched” with “Rebecca”.  Now Rebecca had photos–nice photos.  She had a cute, if not shy, smile, and from what I could tell, was in reasonably good shape.  After chatting for a few minutes, and talking to her on the phone briefly, we decided to meet up.  The plan was for me to pick her up from her place (I guess I didn’t learn my lesson), and grab a bite to eat.

I drove over, excited that I’d meet someone who seemed engaging and cute.  I parked the car, and walked up to her door.  I didn’t have a chance to ring the bell when someone opened the door.  I looked up, and hoped that I had the wrong house.

“Adam, how are you?” she said.  Shit.  It was the right house. Standing before me was a girl who only barely resembled the girl I had been chatting with.  She had a funny looking torso; but I couldn’t figure out why.  She was wearing a sweatshirt and sweatpants (I believe the term is “frumpy”), and resembled a pear.  She had nice eyes, but her smile told a story of dental neglect.  Her teeth looked as if someone had removed them, painted them various shades of yellow, gray, and brown, then threw them back into her mouth.  I’m sure there are British people who would look at her teeth and say, “Oh dear, that is certainly frightening.”  She led me into the house, where I was both assaulted and confused by the sounds and smells of birds.  Every direction I turned, there were birdcages.  Perceptive, she said, “Oh, yeah, my mom collects birds.  She’s a little weird, you’ll meet her right now.”

What???  I was going to meet her mother?  As I turned my head in surprise, I was met by the hollow gaze of an older woman, her silver hair straight but slightly dirty, and her expression empty.  I shook her hand, I don’t even know if she realized that I was real.  She either had some advanced dementia, or she was high.  I didn’t have time to process it before she took me to another room, where her father was laying in bed, attempting to watch TV over the enormity of his beer belly–he must have had a waistline in the low 80s.

After his brief look and ignore, she took me to another room…  Upon opening the door, the first thing to hit me was the stench of mildew, then the surprise of the lack of a floor.  Wall to wall, and I’m not exaggerating, there were clothes, papers, upturned furniture, STUFF, just strewn about the room.  It looked like a hurricane ransacked her room during an earthquake.  Unabashed, she offered me a chair, and got a patio chair and set it atop some of the lower-lying piles.  By this time, my shock had faded, and I was merely trying to breathe as shallowly as possible while trying to determine an appropriate escape route.  Meanwhile, Rebecca decided now was a good time to show me her artistry skills.

Page after page of art was centered around what I’ll call a Fantasy theme; lots of animal-human creatures; what stood out to me what I think was a personified fox head atop a very busty and slim-waisted human body with a fox tail.  I wasn’t sure what the goal was, but I had had enough–and Rebecca noticed.

“Am I boring you?” she asked.  I was shocked she noticed.

“Yeah, well, it’s not that I’m bored, I’m just not into that kind of art…” I explained.

“Oh,” she said, a little disappointed.  “Maybe this will be more interesting,” she said, and before I could say or do anything, she pulled off her sweatshirt.

Now in retrospect, I should have been a little more understanding.  Obviously, she wasn’t getting the attention she wanted from her parents, or from previous boyfriends, or from anyone who mattered to her, and as a result, she was seeking it from random online men.  By stripping her shirt off.

Well, I had been wrong in my initial assessment of her body.  While I initially thought her to be pear-like, I found that that it was not her stomach that gave her a somewhat fat appearance.  No, no such luck there.  Instead, her breasts merely sagged down to where her stomach was.  I must have been staring for 10 seconds or so–she interrupted my thoughts by saying, “What do you think?”  I didn’t know what to think.  By this point in my life, the largest breasts I had ever seen were a DD cup, and these breasts were at least twice that size.  And they weren’t nearly as perky.  In fact, her nipples were a great compass for gravity, they were pointing straight down.  I fought a wave of nausea, and said, “I have to go.”  I RAN out of her room, past her dad, past her mom, past about 1,400 species of birds, out the door, and almost tripped into my car.

I sped home, got into the house, turned the shower on, and took my shoes off before getting into the shower.  I forgot to take my other clothes off.  I took an hour long shower as hot as I could tolerate before feeling even remotely clean.  I then got out, changed, and called Rebecca to apologize for my behavior.

She wasn’t very happy. “That’s the first time anyone has ever run out after I’ve taken off my shirt.”

“How often do you take off your shirt?” I asked.

“All the time.  I show all the guys my boobs,” she explained.  “You’re the first guy who did that.  What, are you gay or something?”

“No,” I replied, “but you’re not what I was looking for.”

We talked for another couple minutes–where I found that, when she wears one, her bra is a 42G.  I think she was telling the truth.  To this day, thinking about Rebecca makes my stomach churn.  The smell of mildew reminds me of that horrible experience, and I hope it never happens again…

After chatting for nearly 3 months, I finally ended up meeting a woman in person. She was beautiful, funny, smart, checked all my boxes.

Back then, I didn't really know that I should invite first-meetings to coffee instead of a meal, and as a result, we were enjoying dinner at my favorite Japanese steak house.

Towards the end of the date, after I paid the bill, she said, "So, I'm not sure this is going to work out. One of my really good friends likes you a LOT, and I probably shouldn't see you."

I asked, "Who is your friend?"

She replied, "Oh, you don't know her, but she thinks you're super cute, so it'd be wrong of me to date you."

I must have looked bewildered. I said, "I don't know her, but she thinks I'm cute?"

"Yeah," she said, "I've shown your picture to her. Anyway, thank you for dinner."

We then parted ways. I never heard from her again, nor did I ever hear about her friend.

Looking back, I'm pretty sure I got used for a free dinner.

Over time, I began to pick up red flags. Maybe I'd ignore them, maybe I wouldn't, but I started to be more respectful of my gut.

Then, there are times when a meeting has a fleet of red flags that are completely offset by the blood rushing to parts that aren't terribly good at balanced decision making.

She was 6'0". Her photos were all professional (red flag #1), and she lived in an area of Los Angeles that was a bit rough (red flag #2). I wasn't sure if I was being catfished or not, but the fact is, most women saying they were that tall wouldn't have lied about it. As we chatted, she told me she was a model (red flag #3), but enjoyed meeting men online because the guys she met on shoots were assholes (red flag #4).

After a few days of chatting, we agreed to meet up. Having not learned my lesson, I drove to her place to pick her up. (Red flag #5, because, why is a woman letting me go to her place without knowing her?)

As I approached, I realized, not only did she live in a sketchy area, but she was in a trailer park. And not a nice one. I considered leaving, but the idea of meeting a gorgeous woman who was so tall commandeered my executive function. I parked, walked up the rickety aluminum stairs, and knocked on the screen--it rattled brutally--and she came to the door. The smell of cigarette smoke overwhelmed my senses--either she, or the previous 50 occupants, or both, smoked constantly. It was distracting...but she was wearing a slinky red dress, nothing too fancy, but her slim frame and perfectly sized curves filled it out perfectly.

I had what could best be described as decision paralysis. She was, bluntly, a specimen. She invited me inside. As if in a trance, I followed.

The smoke smell was worse inside. The walls and ceiling were yellowed from what I'm assuming was nicotine, and the carpet just had that low-pile, old look and feel to it. I was scared to take of my shoes. We stood, talking a little bit; she was glad I hadn't lied about my height, and I just wanted to know what she looked like without the dress...and I found out...she shimmied the dress off to reveal what was, to this the day, the most perfect body I had ever seen.

Except for one thing.

She sauntered over to the table, grabbed a cigarette, lit it up, and asked if I wanted one.

And it clicked. I couldn't do this.

I apologized profusely, and oddly, she was completely understanding. I left, wondering if I'd made the right decision. I'm pretty sure I had.