The Flight Attendant

30s dating

This one was a wild card, she had pictures on her profile of her laying on a beach in a skimpy bikini, labeled 2013, yet other photos on there as well where she clearly did not have that same 2013 beach body.  Her eH “can’t stands” was a man who was sex obsessed – yet later on in conversation she said someone to be intimate with was one of her main criteria.  Ok, I’ll roll the dice on what I thought for certain was a nympho.

Also side note – what’s with the groupings I’ve been dating?  Teachers, business women and now airline related chicks – weird.

Anyway, we never spoke on the phone but would usually text daily.  I was really quite standoffish on meeting this one, by now I know you always trust the worst picture and there was really just not much attraction.  Regardless during a text convo she was hinting so hard that I just had to set the date, which was last Friday.  I’d tour to her part of town.  Me thinking I would leave my car on her street and we’d just walk somewhere close.  Couple drinks, walk back, go home – simple.

So there I am, parked and I text “I am parked on the street” – she replies “pull up, you’re too far down” – then “do you want to come in for a bit”

Keep in mind she lived with 4 other women, so no, I wasn’t about to head into that court room – I hadn’t even seen her yet.  I politely declined.

So I pull up and there she is on the sidewalk wearing a skimpy black dress and she hops in my car.  Attraction, as I figured, was negligible but she wasn’t going to rely on her looks or her dress, oh no, she had her dress hiked up her thighs and I calmly told her “you look good” as she slithered around in her seat being as sexy as she could.  We tried going to a spot of her choosing but there was no parking, I got sick of driving around in circles and just said “can we just maybe go back to your area?”  As she agreed and apologized for the traffic, which clearly wasn’t her fault.

On the way back to her place she said I could park in her condos designated parking spot, and that none of her roommates were home for the night.

I can see where this is going…..

I then said I would have come in had I known she was there alone and we laughed about that as we walked over to a pub.  There we had 2-3 drinks and then I said maybe we could get out of there and go somewhere else, but since I was driving there would be no more boozing for me, and at this time she tells me she has to work in the morning, which she may have, but I am not so sure.

Anyway I steer us back towards her place and she started holding my hand, and then came onto me in full attack mode with lots of tongue, biting and lip sucking…

We got back to her place, continued doing what we were doing but when I’d try to steer us up the stairs she would put the brakes on.  “We have to save that for next time” –
“I am not sleeping with you on our first date”.

This did seem odd, even crazier was the fact she seemed to intentionally open the front and rear blinds to put our little make-out and groping show on for her neighbors.  And that’s all that would be happening, after my repeated attempts to seal the deal she was blatantly using sex as second date bait – but from the 5-minute mark, there wasn’t going to be any second date that involved me.  She probably knew that…

“til next time





The Experiment

I’ve just been on 3 recent dates – three recent dates where it didn’t really matter who messaged me, I would meet her. No judging or pre conceived notions allowed – I would meet whoever, and that is todays blog post…

The Writer

This one came from Match, and to be honest her pictures looked amazing.  If I had to sum her through her pictures it would be “beauty captured” and she was pretty cool in her notes and phone call.  We met and that let me know right away that her pictures had to have been at least 5 years old, it was still her but not the model version I’d seen online.  She was also in her late 30’s, and for me to date an older gal she’s going to have to be bang-on, and this one wasn’t.

Decent convo but not together enough, sketchy job, lived with mom – you get the idea.  She has sent me a couple emails after the fact and has told me to get in touch if I am ever in the area, but I am just not feeling it.

The Pilot

eHarmony, early 30’s, curvy, thick.

This one asked me to call in her first message on the dating site.  I responded with my number (hoping for some aimless texting) but the phone rang instead.  She was one of those “manly” women and had the trucker mouth to go along with it.  She ended up calling me 2-3 times before we even met, which is fine, old school even, but it seemed like she was talking to me as a replacement for someone else.

We met, VERY thick and curvy, VERY loud mouthed, VERY much like a woman who had grown up surrounded by men.

No thanks..

The Social Worker

eHarmony again, one picture (looked good), few messages, she pushed for the meeting right away and no phone call (big mistake).

I said I’d head over to her hood, and did she know of a bar we could meet at – she replied with 3 restaurants.  I pick the first one and say I’ll be there at 8pm on Friday..

I look the place up and its a high-end Italian joint – not first meeting material at all, but I stay the course, at least I’ll get a good dinner out of it.  I get a text from her 10 minutes early, she’s there already and at a table on the patio.  I head over..

She doesn’t look like the picture at all, VERY petite, extremely weird.  I tried, I really did, but after hearing her stumble for words and what not I lost interest.  However, she was all done up, at least 2 hours of make-up invested and she had a really nice dress on.  I don’t think this one went on many dates, if she did she wouldn’t have asked me to a 3rd date or 1 year anniversary Italian place.

I tell her to get whatever she wants, conversation was terrible, bill was $55, we parted.

I hope she enjoyed her food!

‘Til next time.


Oh yeah, experiment failed.





The Girl with No Pictures


Sometimes being a nice guy bites me in the ass.  A little while ago I received a message on match from a picture-less profile inquiring about something that was written in my profile.  I’ve had these before and if the message from the photo-less dater is weak, I just hit delete, but this time I took the bait as the note had substance.

I responded calling her “mystery woman” and she replied that she indeed had pictures she could send, just that for employer related purposes she chose not to have any on her profile.  I said sure, send them over to my email and a few minutes later they were there.  She said “Here are my pictures, let me know if you think we should still chat :)”

Now how the hell can I not respond to that?

The pics were alright – plain Jane to be precise.  Me knowing she was hitting refresh on her browser every 30 seconds looking for a reply, with only her total and complete dignity at stake; I only had a few minutes to make what could be a life long decision – so I sent a reply “Nice pics” along with some accompanying message that started a fury of prompt responses from her.

Her pics were good enough that if everything else lined up we could have something, but out of 10 requirements , only 3 were lining up.  I went for the call and that 3 elevated to a 6 but it started hovering down around the 3 mark when she would make this highly annoying laugh at the end of each sentence. Think of a high-pitched “hehehehehehehehee”.

I felt like Jerry Seinfeld.

Yet I had gone too far, and couldn’t turn back – “Let’s meet up”  – and that meet was earlier tonight.

At first glance I was alright with it, but as the date went on it just became more and more apparent that I should have just bailed way back when I first saw the pictures, or somewhere after the phone call.

I bought us a gourmet pizza and a couple cocktails, we chatted for two hours – her enjoying herself more than I – before my epic yawns induced us to head out.

Her: “Email me or call anytime, unless I scared you away hehehehehehe” – Me: Nooo, *laughs* have a great night! *kiss on cheek*

I feel bad, she’s sitting at home right now envisioning our future and I still have to tell her I am just not feeling it and good luck in your future endeavors.


The Banker


Not long after I began chatting with the VP, I also stumbled upon a late 30’s banker which I honestly didn’t have the highest hopes for.  She had a very bleak dating profile that only had one picture and I got the vibe that she put it together in about 5 minutes.  We sent a few notes back and forth and then went right for the date – no phone call involved.  The date itself had to be delayed by a week as she was in Europe on business but she messaged me the day she got back and we set our meeting for Saturday afternoon drinks – this one caught me by total surprise.

We met on the sidewalk and as she came walking up to me it was apparent she was looking far better than her picture had led me to believe, her body was fantastic as well and we went into the pub for round #1.

Chemistry was instant, conversation flowed endlessly and it wasn’t long before we decided to get out of there and go somewhere else.  We ended up on a romantic roof-top patio and ordered drinks and several hors d’oeuvres.  We then ended up on a couch together and just continued chatting (and flirting) until the sun went down.  We left that place and went exploring again until we found a spot with live music – good live music – $15 each cover charge live music, which she abruptly paid as I only had debit.  She also got the drinks inside.

We stayed there for around 2 hours (now around 1am, date started at 7pm) and we decided we better call it a night.  On the way to the live music we had passed by her place and she described it to me in full detail.  I responded “And you aren’t going to show it to me?” – Her: “Nope!”

She was a good girl.

On the way back, again in deep conversation, she stopped and said “Well this is me” as we were standing in-front of her place.  We tightly hugged, kissed, hugged again, kissed again and then hugged again.  Her clearly beginning to go weak in the knees – knowing the front door was right there, but she held her guns “I am going inside and you are going home” and with that we told each other how much fun the night had been and parted ways for the evening.

When I arrived back home I had a text from her again thanking me and letting me know how nice our evening was together, and I sent one back relaying the exact same message to her.  I let a couple of days go by and then asked her out again this coming weekend and she agreed…

To be continued….

The VP


I think the largest benefit of being an early 30’s dater means I can date girls in their 20’s and 30’s and my past few dates have all been with women over 35.  These ladies are highly established, have killer jobs, chic apartments, nice cars and in this case a house with a pool – and none of them have any kids.

My first foray into dating established women is with a mid-thirties high-ranking VP and I have to say it was from this experience that I’ve now been aiming for more of these well communicative, money-laden and just straight up fun to be with people.  She’s not clingy, not a ticking time bomb for children and brings a sense of ease with her that none of the younger girls can touch.

After a little date-site back and forth we spoke on the phone and it went very well and from there we set our date for a couple of drinks at a nice spot half-way between my place and hers.  We met and hit it off right away, she had wine, I drank beer and before we knew it we were setting up another date in the parking lot a few hours later.  In addition to this she also wants my business services for her company, stating earlier in the date “this just turned into a job interview”.  We have been in touch since the date but haven’t been able to line up our busy schedules for a second meeting, but we will be soon.

To be continued..