1994 called, it wants its pen pal back...

I hope you're enjoying yourself so far.  I'm hanging out somewhere between excited and depressed.  Each new message holds the promise of a lasting relationship, but my hopes are almost instantly dashed when they ask me if I like to fish.  Somehow my profile gives men the world over the impression that I'm an avid angler.  I must investigate this. 

At any rate, I'm starting to see a common problem among the guys on these dating sites.  I call it the pen pal syndrome.  They say they're looking for a relationship - some of them even go so far as to say they're looking for marriage.  However, their actions, or rather inaction, would suggest that they're actually looking for a good old-fashioned pen pal. 

Here's the thing, I suck at being a pen pal.  I'm the girl who will gladly take down your address at the end of summer camp and then never write you a single letter.  I'll intend to. Oh, I'll intend the crap out of that, but I have zero follow through.  I always feel bad about it at some point.  Not bad enough to write an actual letter, of course, but mostly I figure all I've missed are some stupid chain letters.  Does anyone else remember those?  Send this letter to 10 people or you'll be alone forever.....wait a minute...okay...sort of putting it all together, this whole me still being single thing.  Dammit!

So here's how the online pen pal situation goes down.  The boy starts the messaging conversation (that is, the few who actually will start a conversation in a non-creepy way).  I participate if I deem them worthy, having the same "get to know you" conversation I've been having with all the other guys.  If it's going well, the conversation will find a groove and it will start to feel more like a real conversation and less like a CIA interrogation.  Mostly, the conversations don't feel as natural as I'd like, but I'm usually satisfied enough by their reading comprehension and basic writing skills to continue talking.

Here's the problem - Most guys never show any signs of stopping the conversation.  Only a brave few will take the initiative to mention meeting in person, and then an even smaller group of those guys might actually follow through with a plan to meet. But at what point do you acknowledge that you've fallen into a pen pal relationship, the dreaded "friend zone" of the digital dating scene? 20 messages?  40?  Do you count by days or weeks?

I suppose what they're wanting is for me to do all the work.  They want me to start the conversation, give them my number, ask them to call or text, and make a plan to meet up.  That way I can be the rejected one.  Well newsflash, all you little cowards, if I've participated in more than 20 messages, I'll probably agree to meet you, or at the very least, give you my number.  After all, isn't that what we're all on the site to do?  It's not like the guys have to wonder, "gee, she's really pretty; I wonder if she's seeing someone?  Would she think it was weird if I started talking to her?"  No, you moron, I'm on a dating site!!!

Over the past week, I've had a few of these confusing interactions, and I expect to have more.  I'll detail them for you now, because I know you want details:

• Day 2 on the site, I was winked at then messaged by a 30 year old airplane mechanic with a little war experience.  We'll call him Tinker Tailor Soldier Spy (TTSS).  He was really smooth about getting my number, and we switched to text after about 30 minutes of consistent messaging. We proceeded to text pretty steadily for the next few hours.  It was a great conversation.  He understood my sarcasm, IN TEXT, without needing any explanation!  I don't have to tell you how rare that is.  He was engaging and funny.  We joked about serial killers, but not in a creepy way (I guess you had to be there).  It was really special.  He mentioned meeting up and I agreed, but then we just kept texting and he never mentioned it again.  At the end of the conversation, I told him to contact me again if he wanted, and it's been crickets ever since.
• I'm currently stuck in a vortex of messages with a guy I'll call OSU Enthusiast #1 (I'm just assuming there will be others in the future).  We've exchange 25 or so messages with no end in sight.  The conversation is not flowing, yet he still keeps asking me mundane questions.  I may have to cut him off soon. It's for his own good.  At this point, if I met him in person, we'd have nothing left to talk about.
• We all remember East India Trading.  He asked me for my number, asked me to meet, then immediately told me he felt no connection with me but offered to meet me anyway.  Gee thanks for the offer of a pity date, but I think I'll pass.  I can find plenty of ways to humiliate myself without making small talk with the likes of you over $5 lattes.
• A boy I'll call Not Cute Enough to Judge Me (the name is pretty self explanatory) texted with me for an hour or so my first night on the site.  We got along okay.  He asked me for more pictures - not as sleazy as it sounds - I only had 2 pictures on the site at that point because I hadn't updated my selfie stock yet.  When I sent him the only additional pictures I had that still remotely look like me (I've recently lost about 40 pounds - yay me!), he never texted me again.  I have to say, that was really good for my self esteem.  Really I guess that wasn't a pen pal problem, but I'm just mad, and I needed to vent about it a little.  Thanks for listening.

I suppose the simple solution would be for me to take the initiative and boldly ask them out.  In doing that, I feel like I'm the only girl on the planet who's not worthy of being pursued.  It's a total killer to my self esteem.  Didn't the Lord wire these guys to to chase me?  I mean, what kind of story does that make for our grandchildren?  Well, you see kids, your grandpa was shy, so he sat in his cockroach infested apartment, surrounded by empty pizza boxes and well-worn Victoria Secret catalogues, culling through endless lists of profiles by the neon light of his Budweiser wall lamp.  He waited patiently for me to find him.  I sent him six messages before he finally decided I was serious enough to message back.  He got to know me by email over the next few months, while grandma's eggs dried up, and finally his apathetic technique paid off.  In a moment of sheer panic at the prospect of turning 40, I finally asked him to meet me for a date.  This, kids, is the stuff dreams are made of."

I think it's safe to say my boy chasing skills rank somewhere below my ability to cut my own hair.  Trust me, if I had any boy chasing prowess I would not be writing this blog.

In other news, Geek Squad is looking better and better, if only for the fact that he actually knows how to ask a girl out.  Good for you, Geek Squad.  Huzzah!*


Today's Updates

• First off, a scary story - I have permission from the victim of this particular incident to share this story with you all.  A friend of mine is on the same site I'm on, and she had been talking to a gentlemen for a few weeks.  They made a plan to meet and have been talking on the phone every night leading up to their date.  It seemed like things were going well, then yesterday, out of the blue, he asked her for $6500.  She obviously did not send him any money, but instead, quickly reported him to the site administrators.  She later learned that several things in his profile were fraudulent.  This was a good reminder for me that until you actually meet someone face to face, you really don't know who they are.  And in fact, it will probably take a few face to face meetings to really get a feel for who the person is.  Be careful!  Sometimes boys are creeps.  And here you thought this blog was just for funny stories.
• On a lighter note, I'm getting psyched up for my date tomorrow with Geek Squad, and I'm trying to figure out what I should wear.  We're meeting at 7pm, so, in theory, I'll have time to go home and change.  He'll be coming straight from work, but I'm not sure what his normal workday wardrobe is like.  I could wear a cute, casual dress or skinny jeans and a t-shirt/sweater combo.  Keep in mind, I've lost almost 40 pounds this year (I never get tired of saying that), and I've got more to go, so my wardrobe is pretty limited.  I'd love some help on this!  Please post some thoughts in the comments before tomorrow night.  Also, I'd take any pointers on conversation topics. Those of you who know me best are shaking your head right now, because you know I can pretty much talk to anyone, anytime, but I'd be interested in having a few back-up conversation pieces in mind in case the conversation lulls.  If in doubt, I'll just order another drink.  I see no potential problems with that plan...
• Old Ginger Spice and I are still going strong...at least as strong as you can go when you've never actually met.  He sent me a great, lengthy message last night, and I definitely responded.  He's a one message a day kind of guy, but he covers lots of topics in each one, so it's worth the wait.  He just sent me another lengthy message tonight....and....he asked for my number so we could "text or chat or prank call each other."  How cute is that????  I'm probably more into him than I should be at this point, but his emails are so funny and engaging that it's difficult not to be.  We are definitely going to have to meet sooner rather than later, but I'll give him a few more days before I get too antsy.  I don't want to show all my crazy at once.
• I'm exchanging messages with a few other guys who aren't interesting enough yet to warrant nicknames.  Should they become interesting enough, you'll be the first to know.
• I've cooled conversations with a few other guys because they can't come up with a question to ask me in return.  Conversation is give and take.  I can only give for so long before I have to pull the plug.
• I have my age parameters set to 25-40, but I think my age cut-off is closer to 42/43.  I keep getting winks and likes from guys in that early 40 range, and some of them are appealing.  However, when I get any action from a guy older than that, it just feels creepy.  What is a guy in his mid-fifties doing scamming on a 31 old?  Shame on you!

* That's the first time I've used "huzzah" in my life.  I've been meaning to for a while.  It seems like something the cool kids are doing these days.  I didn't like it.  I don't think I'll do it again.  If you take nothing else away from this blog, remember that nothing good comes of giving into peer pressure.