A Date with a Man!

Well, I entered the online dating world, and it sure has sucked!  After my short stint and no prospects, I got a great deal (of course) to renew my membership, so I decided to try suffering once again.  Here's my perspective on online dating... if you aren't a strong woman, it can really hurt your self esteem.  Seriously.  It's hard to not take offense when a guy doesn't respond to an email, a like, a wink, whatever.  Does he really think he's better than me, and I'm not worthy of his time and attention?

As soon as I renewed, I decided to change my picture, and I immediately got a few men vying for my attention.  I find it interesting that that would change things, but it did.  Anyway, I got an email from a guy who is 50 (gulp!) years old.  (I'm almost 42.)  He doesn't look close to being 50 and he takes good care of himself, and really, age is just a number. He's attractive and seems to have his shit together, so those are good things. 

We exchanged some thoughtful emails, and I told him that I am a SMC and gave him an "out" if he wanted.  I understand it's hard dating someone with kids, especially when there is no ex-husband who takes the kids every once in a while.  Furthermore, I have no family in the same state, so I'll have to start forking out money for a babysitter which I don't want to do but will have to do.  So everything I just typed were his concerns, and I totally get it. Just the thought of juggling dating with a kid makes me crazy!

This guy has never been married (came close) and doesn't have kids, but he really does like kids.  I feel like he has such a footloose and fancy free life, and I... don't.  I'm not so sure how much he is going to want to share me with my son, have to make plans ahead of time, and not being able to do spontaneous things if Sidekick is not invited. Again, stressful.

Last night we talked on the phone for two hours. He brought up the whole kid thing and babysitting issue and even made a comment like I'd never really be able to stay the night at his house.  Yep.  You got it, buddy!  I'm not paying a babysitter overnight just so we can sleep in your bed.  My bed is big and comfy and will be just fine.

We have an unofficial lunch date tomorrow.  Last night I suggested we meet for lunch.  Why?  Because I don't have to pay for a babysitter and lunch seems much less stressful.  He's on vacation from his fulltime job this week, but he has a side job, so he's not exactly sure when he'll be done. I work out of my home and will be out an about with customers.  It might be a bit of a challenge, but I told him in a text that I have to go about my day because it is a work day, and we'd have to play it by ear if we will be able to connect.  That might have pissed him off.

Who knows what'll happen.  Part of me is ready to date, and part of me is scared shitless.  How does a man gel into mine and Sidekick's life that has just been the two of us for a little over three years?  I want to find a man, I really do, but dating brings a new set of challenges now that I have a child.

Sidekick keeps asking me when he is going to get a Daddy.  As if it is that easy.  If it was, I wouldn't have him, I'd have an entirely different kid from free sperm. I keep telling him that one day I hope to find him a Daddy.  He reassures me that we have great family and we are a great team.  Bless his sweet, innocent heart.

No one knows about this potential date.  I don't want anyone to know unless it truly goes somewhere.  But I'm tempted to ask my friend about him because she happens to be Facebook friends with him.  However, my secret investigating might be a little too much and seem very sneaky to her, and I wouldn't want that to get back to him.  I guess I'll wait to ask her if in fact I'm interested in him.  There are so few secrets in the world with social media, and it's easy so Google people. 

Update tomorrow if there is an actual date...