What I’ve Learned From Over 35 Online Dates In 6 Months

dating in your 30's

Back when I started online dating I never figured I’d meet so many women, but I have and my goal was to at least try to learn something from it – as it was always in the back of my mind that I probably wouldn’t find a girlfriend from it, so what have I learned?

Some basics of course, online dating sites are literally meat markets and you’re always looking for someone better than who you may even be communicating with at the time.  You may be into the person you’re conversing with, but you’re going to have your feelers out for something better – this goes for both sexes.  The thing I learned is that there never was anyone better, but many that were indeed worse!  After learning this (the hard way) I would only focus on that person, but my stip was that it was one from each dating site.  Girl from Match would see that I hadn’t been online in 3+ days, but meanwhile I was trolling eHarmony, or vice versa, and texting up to 4-5 girls at the same time at various stages of the meet and greet process.

Another important thing is that the person you met online will never be the person you meet in-person.  This is a fact.  Once you can get your head wrapped around that you’ll naturally become open to meeting people who may not have formerly met your online dating standards.  For me, if the picture was good and they had their acts together I’d usually meet them and many times I was pleasantly surprised with whom I was sitting there having a date with.  Some people just can’t digitally express themselves in the same light that they do in real life, or even on the phone.

Of course this backfired in spectacular fashion more than a few times, but that’s ultimately the risks we take when essentially meeting strangers from the internet.

Another important lesson I learned the hard way is that online dating sites are literally filled with people on the re-bound – always ask when their last relationship was before bothering to meet.  Many I asked had just gotten out of long-term relationships less than 3 months prior – and I do not believe anyone is over their ex in such a short period of time.  I’ve even done this in the past!  After the date (which only made me miss my ex even more) I realized I had to take time for myself and I deleted the dating profile.

One more thing is to meet your dates sooner than later and keep chit-chat to a minimum before hand.  If you do this, you’ll actually be meeting a new interesting and attractive person (if their pics are legit) versus “dealing with” someone you’ve just spent 2-3 weeks talking with that isn’t measuring up to what you had envisioned.  It’s really that simple, one or the other – choose to meet the new person that you don’t know much about instead!  The less we knew about each other the better the date was, even if it led nowhere.

Til next time’





The Cougar Rejection


For awhile there I thought it was advantageous to date women that were older than I.  Not incredibly older (I am 33), but ladies in the 35-38 age-range seem to like me (or I should say, seem to like my dating profile).  I had two of these on the go at the same time, one 36 and one 38, this is the story about the 36 year old.

The 36 year old made me her favorite on the dating site and liked a couple of my pictures and she was truly a knock-out in the looks department.  Our chats were playful and fun which quickly moved to daily texting.  I had gone for the meeting pretty early on, but she was always busy with work, family or “life”.  She almost lost me after we’d agreed on a time to phone each other, but all I got was a text “I haven’t forgotten about you, currently grabbing coffee with a friend after yoga”.

No “sorry I can’t chat tonight” – all I got was the message above.  Keep in mind, during this time I was head-over-heels with the build up date girl, so interest in this one was minimal at best by now anyway, which was around 2 or 3 weeks past our first chat – still no meet, and now not even a phone call.

However we did finally agree to meet on a Sunday afternoon for coffee (the day after the build up girl flop) and my hopes of anything more spectacular happening were very low indeed.  I got to the place a little late, parked the car, texted her that I was there and ran inside.

I looked around and saw nobody fitting her description..

I then went back out the parking lot and texted her “I think I am at the wrong location”

Turns out I was at the right location, she was up the road at the wrong one.  She said she’d drive down and meet me after apologizing..

This was when a new white BMW pulled in, it was her, and she was even more gorgeous in person.  We went inside, chatted for hours, laughed and had fun before being told the place was closing and we had to leave.  During out chats she had suggested second date ideas, and I quickly agreed to them.

Then in the parking lot she asked not once, but twice, “we’re going to stay in touch right?”

Me: “YES!”

I left there on cloud nine – could this be the one I’ve been waiting for?  She was hot as hell, cool as hell, had a killer job, own home, nice car, we got along awesome – I was literally ecstatic.

Two days later we were texting again, just as playful as we had been before and I asked to meet up with her again the following weekend.  She said that it was too early to make a call on that as she had family visiting from Europe and she’d likely end up showing them around.  We texted back and forth a few more times and then one day she didn’t respond.

I didn’t really think anything of it – she was indeed way busier than I was and also had family visiting.  We didn’t text for over a week, and my gut told me this wasn’t good, so I sent the “feeler text” to see where things stood.  “Hey you, did you have a good weekend?”

And I got back what I pretty much expected – I am a great guy, easy to talk to but she’d met a guy a week after me and felt he was a better match than I was, and to take care and be well”

I didn’t respond – but I don’t believe her either.  She had told me about using that excuse during our date regarding a guy that was begging her for a chance and wouldn’t stop sending her messages.   I was also just on the dating site to delete her messages and saw that she’s been on today as well.  Why be on there if you’ve just met your epic soul mate a week earlier?

Better yet – how could you go from 2nd date ideas and begging to stay in touch to pretty much “leave me alone”.

I’ll never know – but the fact that she was divorced might have something to do with it

And Thats Why You’re Single Baby…


Another day, another Eharmony candidate – another “wild card” if you will.  This one and I had been tossing BS banter back and forth for a couple of weeks and she was one of the ones that fell into “mystery woman” territory – and I love a good mystery.

One picture, far away, with big black sunglasses covering half her face – kneeling down, half hiding behind someones kid, but she was thin.

I am game.

Messaging was light, texting was light and I barely even knew what she looked like.

“Ok, meet you at 8pm on Wednesday”

She got to the spot first and sent me a text “ask for S when you get here, I am already seated” – Oh great.  I arrived 5 minutes later and walked in, a quick glance didn’t show any girls sitting alone from what I could see, so I squeamishly asked the male hostess ” I am looking for my friend S”

-Right this way sir, have you been to this location before?-

“No” – as I am watching like a hawk for my prize..

Then we rounded the corner and there she was.  Diamond earrings, tight black / lace dress, make-up – the whole bit.  Keep in mind I am in jeans, an un-tucked button-down and black Lacoste shoes.  Not on par with this tanned, black haired, red lipstick wearing rocket in her little black dress.

Awkwardness wasn’t an issue though, yet.

This chick had been single for 2-3 years, she’d traveled alone all over the world (her preference), worked downtown and was pretty much – as I’d soon find out – set in her ways and very stubborn.

We’d both already eaten, but I asked if she’d like to split an appetizer or something “No, I can go right to desert” before she ordered a big piece of chocolate cake covered in whip cream and various vanilla and chocolate sauces.

I ordered a beer – knowing full well it was unlikely I was going to want to see this one again after hearing her tales of abandoning various friends and family on trips after they wanted to take a shower lasting longer than 5 minutes, or asking to bypass the bush toilet in favor of one at a restaurant down the street.

“They just don’t understand that it’s my vacation too, and I am not waiting around on their bullshit”

These stories came in tidal waves, essentially equating to “me me me me me me me me me me” as she was scarfing down chocolate cake.

I was truly mesmerized by her antics, this girl truly didn’t care what I thought and if I may project for a second it may have even been a test.  I didn’t care to really know though.  She had told me of a job interview she’d recently had and as we exited the establishment and approached the parking lot we said our farewells before I went in for a quick hug and said “Good luck with that job interview eh”

As I turned and went for my car..

These mysteries aren’t ever as fun as I anticipate

The Build Up Date

texting before date

Usually after a bad date I just laugh it off but this one still has me a little uneasy.  This one clearly qualifies as one of the worst dates I’ve been on yet, simply because it involved one of the biggest dating no-no’s that there is.  And that was a lengthy build-up via text messages before actually meeting.

Allow me to explain..

She came from Match and was actually one of those profiles that pops up right after you have sent someone else a message

“If you like that one, you’ll like these profiles too”

She responded sometime later, we did the usual on-site back and forth before I moved it to texting to set up a date.

Simple, right?


She was also one that once a text was sent, you were stuck to your phone until she went to bed that night because she would respond within 30 seconds and continually ask more and more questions.  I even had to lie about “company arriving” while I was at my cottage just to end the text-madness from her so I could enjoy the peace and quiet.

A day or so after when we got into another text flurry I simply asked if she was free to talk on the phone – to which she said no.  She hated talking on the phone, but was free to text all night.

Why do you hate talking on the phone?  “After work I’d just rather text if that’s alright, I hope you don’t think I am a freak”


But she gradually got deeper and deeper with her conversation and I stupidly engaged.  Then she started calling me baby in nearly every message.  She told me how she was so delighted to meet me, how she didn’t think guys like I existed anymore and how she had told her sister and co-workers about me, even showing them my pictures.

She even asked me twice why I messaged her on the dating site in the first place?

Her pictures were hot, she was the right age, good job, car, sweet place – I didn’t see what the big deal was?  Yes I’d been out with hotter girls but that isn’t my priority – so I just told her what sounded good and we’d continue chatting away, via text messages.

Then came the date delays, which in total took 3 weeks to meet and the date being moved three times due to her silly work schedule – and continually she would text me all day and night, getting deeper as the days went on.  I even had to tell her “You know there is a chance this isn’t going to work in person after we meet” to which she agreed but now was in full on soul mate talk and the worst part was that I was starting to believe it and develop feelings for her.

I (actually we) anticipated the date and even counted down the hours.  I even arrived 45 minutes early so I’d be there first.

And she arrived.

I’ll say the bulk of her pictures were 5+ years old with one semi-recent picture that had been taken at a slick angle as to not show her true hip size, which was substantial.  From there we went into the coffee shop (where she actually paid for the drinks!) before we sat down to talk.  First thing, this girl was NOT who I thought I was chatting with over the previous two weeks and I am pretty sure I wasn’t the guy she thought she had been “talking” with either.

This was very awkward.

No more baby talk, no soul mate stuff – nothing.  Her texting vigor and openness had literally vanished and I was left with a bigger and older version of what I’d seen online – that talked about boring stuff.  In an attempt to rejuvenate things I suggested we go for a walk, which we did.

During texting the night before she told me how much she couldn’t wait to be hugged by me and that she would prefer some affection.  So during the walk I put my arm around her, and it was one of the most awkward things I’ve ever done.  I quickly pulled my arm back after a few seconds as it just felt so wrong and out of place.

We walked a few more blocks before turning back towards our cars, now I was pretty much just walking and not even saying anything – this date sucked.  We had originally planned on hitting a couple of bars and having drinks but in no way was that happening now, and this was also a Saturday – not a day I like to waste on shit like this.

Back at the cars she told me it was nice to meet me, “talk soon” (yeah, right) before I said goodbye and got out of there.

Never again will I knowingly enter myself into a build-up like that before a date again, what a let down.  It even stung as I hit delete on the 1000+ text messages from my phone.

Remember: Building expectations guarantees a bad first impression because they weren’t what you were expecting (and vice versa)



The Rebounders…


Over the many women I have met during this online dating tenure I can now sit back and analyze.  Certain patterns were the same with a few that I now realize were simply fresh out of relationships and on the rebound, hard.

The latest hammered my theory home.

She had sent me a note on match, she was gorgeous and I quickly engaged with her.  After a few messages we moved to texting and then set a date for the following Thursday evening.  I would park in her vacant parking spot that was in the underground at her condo and then we’d walk to a nearby place for a drink.

I let her know I had arrived and I awaited her to come downstairs and lead us into the underground parking.  As usual she wasn’t as hot as her picture but she was still very attractive, she hopped in, we parked the car and then made our way to a bar.

It had its (bad feeling) moments at the start but after 15-20 minutes we were deeply conversing, laughing and generally enjoying ourselves – but I still wasn’t sure what she thought.  Although the reddest of red flags popped up during our chat which was “Yeah its easier for you to park at my place, my ex use to park there, so its been vacant for around 2 months”

Ummm – what?

It truly put a damper on things for me but maybe it was a short term relationship or maybe she meant to say 2 years (yeah, right) but I was physically and mentally attracted to her so I didn’t pull the chute.  It started getting late so we decided to head back – me still not 100% sure was into me, but she seemed like it.  As we entered the parking garage we had the “well I really enjoyed myself” + hug which she followed up with “I really hope we can do this again”, which honestly caught me by surprise.  I said of course we could, just next time on a weekend and not a work night to which she agreed, thanked me and we parted.

I sent her a text on Saturday, she replied enthusiastically initially to the first, but not my second text which was a legit question – odd but this girl would go 24 hours sometimes for a reply so I thought nothing of it, then the day after I tried to set something up for the following weekend and was hit back with “I just don’t think we have enough in common to make this work, best wishes”

Her dating profile is also now set to private – met someone else?  Or just not ready to date yet??

Regardless, I’ve seen this behavior from other girls too and it always left me scratching my head on what caused the 180 and I think I found it, they’re on the rebound.