Speed Dating: Just my random thoughts hitting all sorts of things

I had a lot of thoughts running through my head on things to update you all on, but I didn’t want to write a new post for each individual one. So I figured I would knock them all out here.

First, things with Lola have lots of potential. We’ve hung out a few times and have a great time together every time. We haven’t had what I would call our official second date yet, since we have only hung out together for an hour or two just to spend some time together having lunch together or something. No, we haven’t had sex yet. Is that all you people think about?

Speaking of sex; things with Krystal are fading out, and fast. She recently started a new job so I haven’t had the same exposure to her that I normally had. But she is very clingy and a little intrusive. She’s always telling me she misses me, and has even been asking to come to my son’s baseball games and come over after he goes to bed at night. I’ve had to shut her down more times in the past week than I would ever care to.

We also had to have “The Talk: Deuce” because after the initial version of “The Talk” some things started coming out that I wasn’t really cool with. When this whole thing started, I was under the impression this was just going to be a fun FWB thing, and that her husband was cool with it. Well … apparently he doesn’t know about me as much as I was led to believe. She says he is rather naive and clueless and has no idea of what she is doing. She isn’t happy in her marriage and doesn’t leave because of the kids. She told me earlier that she was “happily married and in love with her husband” several times. So, the tapestry is unraveling. And now I’m not as comfortable with this as I once was. This is definitely a different scenario than what I signed up for in the beginning, and I thought I was pretty blunt and honest with her as to what I was looking for. She wants to get together next week after I get back from my long family weekend trip to Texas. I am not really interested and kind of dreading it. Especially with thing going well with Lola and the possibility of another upcoming date (with Miley). I think it’s about time to end this bad MTV reality show I’m living in. I’m not desperate enough to need sex that bad to need to hold on to this arrangement.

And remember, I told you that my luck would change once I started down this Ashley Madison-inspired trail. First Lola comes along right as things with Krystal and I get started, and then Miley, with whom I’ve had only 2 messages with previously, comes jumping back into the picture, after a few weeks of nothing. So I figured I’d at least have a quickie date with her for lunch or something to see how things look. I don’t juggle girls very well, so I’m not really interested in dating multiple girls at the same time, but I guess I can’t also dismiss one without at least checking it out first. You never know what might happen. All the more reason to get rid of my clingy, married, side piece.

Lastly, I am still looking for any feedback or suggestions on what you guys would like to see from me on here. Any additions, topics, whatever. You name it and I’ll consider it.

Thanks for reading and have a great Labor Day weekend.

Keeping it fresh: What do you want to see?

Wow, this has been going a lot better than I thought it would when I started. But it can always be better. I’ve got some great regular followers and lots of random passers-by.

I’ll still keep doing what I am doing and filling you guys in on all my dating antics. But what I want to know from you is; how can I make this better for you? What do you want to see me talk about? What features do you want me to add?

I’m just looking for a little feedback from you, my readers, to see what would keep bringing you back and help spread the word.

Thanks for reading and I look forward to your suggestions!

Lola: I took a shot and hit the target

Background: Lola is another one of my Match dates. She didn’t send me any messages or winks, but she liked a few of my photos. So I checked out her profile, liked what I read and saw, and decided I’d just send her a note thanking her for admiring my photos and just made some small talk. She responded, and we started talking from there.

She was ending her time on Match after only about 2 months because she was having to block too many guys, hide her profile too often and was even thinking of changing her phone number because of all the creeps she’d been meeting online. This has been a broken record lately, talking with girls who are fed up with sites like Match because the guys are too creepy, inappropriate or over-aggressive.

We’d been emailing back and forth for a few days until her paid account expired, then she gave me her personal email and things were going very well. I took a little extra time before offering up texting and calling each other because I didn’t want to seem like I was just like all the other guys she was talking to. Even though I got a sense that she didn’t think of me that way, I still didn’t want to push my luck.

But I did NOT want to play myself into the FriendZone. So I offered up my phone number and things took off from there. No hesitation on her part to text me, or call me, so things were looking pretty solid.

So after a couple of weeks of talking/chatting, I finally had a free night coming up and we set up a date. She’s a hairdresser and has a unique schedule where she has alternating weekends off, and has Mondays and Tuesdays off. She usually doesn’t have Fridays off, so she took a vacation day so we could go out Friday night.

A little about Lola: She’s tall (5’11”) – which is a weakness of mine, attractive, in her low-40s (just a bit older than me), never been married and doesn’t have any kids of her own. But she’s very much a family person, loves kids and is very involved with her nieces and nephews. I haven’t asked about the “no kids” thing yet because that is kind of a sensitive issue. Maybe she can’t for some reason and I don’t want to broach that subject too soon, especially since having kids is not any sort of priority for either of us (her profile listed that she didn’t want kids but it was ok if her partner had kids).

I kicked around some new and different ideas for our first date. I thought about taking her to a baseball game just to do something a little non-traditional, otherwise we’d just do the typical dinner and dancing idea (since she mentioned she likes to dress up and guys don’t take her anywhere which requires her to dress up). So I came up with a very non-traditional choice, but wouldn’t tell her what it was, trying to keep things interesting. I let her know what she should wear (casual clothes), but that’s really all I would let on.

The Date: Based on where we were going and our time constraints because I had to drop my son off at his friend’s house, she agreed to drive to me because it would take about 2 hours for me to drive out to get her and come all the way back. Thanks to rush-hour traffic, it took quite a bit longer for her to get to my house than originally planned, but it wasn’t a big deal.

I was so relieved when she finally got out of her car that she looked like her pictures and like she described herself. She was tall, slender and very cute. We were already leaving many of my previous dates in the dust at this point, and we’d barely said “Hello” yet.

We chatted as I drove to our initial date location, but I still didn’t tell her where we were going. As I turned down the street to our destination, I asked her if she had ever fired a gun before. She replied with much more excitement than I expected, “Is that where we’re going?” When I responded affirmatively, she was so excited.

At this point, I figured the rest of the night would go smooth, because I thought this was the “make or break” moment. Either she would hate the idea and the date would suck, or she would love it and the date would go great. Thank goodness it was the latter. I had also read in numerous places that taking a date to a gun range can really get the endorphins flowing.

It worked like a charm. I gave her some instructions on how to hold, aim and fire a handgun. Of course this meant plenty of opportunities to get close and touch her. That really seemed to break the ice so much faster. And we had to get real close to talk to each either, too, since it was so loud inside the range.

I could see the surge rushing through her after she fired off her first shot. I let her fire about 75% of the shots, since I’ve fired countless numbers of rounds in all of my years in the military. I would step in every once in a while to fire a few rounds when she needed a break because her hands and arms were getting tired. I helped with more instruction, gave her advice, and helped spot her shots so she knew where she was hitting the target. For a beginner, she was doing outstanding. She would generally hit the target within a 3-inch radius of where she was aiming and was keeping her shots in tight groups. That is something military and law enforcement practice hard at being able to achieve. She was a natural.

I expected to only be there about an hour, but almost 2 hours later, we decided to head to dinner even though she would’ve stayed longer to fire more since she was having so much fun. We even kept the targets so she could have them as souvenirs and take them home. I even took pictures and video of her so she could have them all to show her friends and family. She really appreciated that and couldn’t wait to show the girls at her salon.

The next stop was a live music spot in my part of town that I had been wanting to check out for a while. It is supposed to be a jazz/blues club, but also has bands that play some rock as well. It is also billed as one of the top local barbecue joints in the area.

We got there after 9 p.m. and found a nice spot up near the front. The place was almost at capacity but there were a few open tables. We ordered a few beers and the barbecue sample combo. The food was outstanding, but still took second place to Lola.

We had such good, easy conversation while we ate and listened to a local 3-piece blues/rock band. We had lots of laughs and never ran out of anything to talk about. I found ways to talk mainly about her and her career, and stuff like that. I am not much about talking about myself. Time flew by. We even managed to find ways to continue to casually touch each other – always a very good sign on a date. The next thing we realized, it was about 11:30 p.m.

As we were getting ready to leave, I apologized for making our first date so loud so we basically had to yell at each other all night just to have a conversation. She laughed it off and we decided to go somewhere much more quiet to talk for a little bit longer. So we headed to my place for another beer or two and talk.

At my place, we cracked open a couple of beers and talked for a little while longer. I had a been a fairly good boy to this point in the night, and decided I need to make my intentions known and made my move for the kiss. After that, everything was glorious. It was great. We made out for a little while – kept our clothes on the whole time (in case you were wondering) – and then sometime after 1 a.m. I suggested it would probably be a good idea if she went home before things got into some dangerous area.

I walked her to her car, gave her directions how to get back to the highway (since I had to walk her in to my place earlier), and we kissed a bit more. As always, I made sure she let me know when she got home. About 2 a.m. she texted me she was home and we exchanged a few more messages before going to bed. Things were looking very promising.

Post date: Like I said, things are looking very promising. We’ve been talking all day and have even planned another “date” for Monday afternoon, since she doesn’t work and I don’t have class.  I want to make sure I see her again this week because next weekend I will be out of town for Labor Day weekend and won’t be able to see her for almost 2 weeks.

Now, I have to figure out what this means with the whole Krystal situation. She was constantly texting me last night during the date, but I was ignoring them because I think it’s rude to keep checking your phone on a date. I have to check to see who it is, in case it is an emergency or something with my son, but if it is someone else, I ignore it and don’t respond. And all that did was make it worse because I was ignoring her. Ugh.

Grade: A

Thanks for reading and stay tuned for more!

Premature ejaculation and farting all night

Hey-oo!! Bet that grabbed your attention, didn’t it?? You’ll see where I’m going with that in a bit, but trust me, that has NOTHING to do with me!

First, an update. I had “The Talk” with Krystal about what she was expecting from me in this swinging relationship of hers. After all of the comments and hints of jealousy, I expected a lot more drama. But basically, she saw things my way. She agreed she would have no reason to get upset with me for seeing other women, especially given her situation.

She did ask that if I was going to get into a serious/sexual relationship with a girl, that I let her know and we part ways at that point. That’s totally fair. I mean, if I was going to have a sexual relationship with a legitimate girlfriend prospect, I would definitely end things with Krystal first.

There is no way I would start a potential serious relationship having a side piece in my pocket just for sex. I mean, if that’s all she (Krystal) is there for, and I can get sex from my new girlfriend, then what’s the point of keeping her (Krystal) around? There isn’t any.

And she respected the fact that I brought it up before I did something “wrong” and upset her.

Deep down, I know she doesn’t like the idea of me seeing another girl, but she knows she has no room to say anything about it. Even though this has been interesting and kind of fun, I am really (honestly) on the lookout for a serious girlfriend candidate.

The good news is, I have a date with a new candidate Friday night with Lola – the tall hairdresser. Stay tuned!

Now for the good stuff.

I have a friend that used to be a co-worker with me back in days in the Washington DC area. She still lives there, and we keep in touch every now and then. We are very similar yet total opposites. She writes a dating blog as well and we share stories, swap advice, and all the fun stuff like that.  Recently, we had been talking about her wanting to have “The Talk” with this muscle-head teacher guy she was dating. They went out for a few weeks and she was ready to get exclusive with him, and they finally had sex.

And that’s when things went sour. He kind of dropped off the radar (I’m over simplifying this) and then eventually stopped returning messages all together. When this situation of him not responding to her first started, we discussed her needing to have “The Talk” with him. So she set a time to have “The Talk” with him the next time she saw him, which was on their regular Thursday date (last week). The date never happened because he never responded to her.

A few days passed, and finally enough was enough. She could not let this disrespectful behavior go unnoticed and unpunished.

Before I get to the juice, know that the worst thing you can do – especially after having sex – is end any sort of relationship by just “ignoring it away.” Have the guts to at least say something as to why you’re done with the relationship. It’s the respectful thing to do. Sure, we’ve all had first dates where you never talk to the person again (I’ve done it and it’s happened to me), but I’m talking about relationships where you’ve started to invest yourselves in each other. Even though it will hurt, it’s the right thing to do. I do it because I would like the same courtesy.

OK, now on with the show.

She told me she’d had enough with this dude and wrote him a serious nastygram. I am sharing this letter with you, in its entirety because I loved it SO much, I asked her if I could please share it with you. She agreed, mainly because she wasn’t sure about posting it on her blog. So for your reading enjoyment, her it is.

“You’re a coward. I was gonna stop by Rhino and ask you what made you pull back so fast. But I didn’t want to scare you. It’s just really inconsiderate to totally stop communication the way you did. It’s immature. Even if you thought my feelings would be hurt, you should have shared your thoughts.

You complain all the time about lack of respect and common courtesy from people, yet you can’t even give it. Maybe that’s why you don’t receive it.
I think I was more than kind to you. I took into consideration that you fight depression and I tried to give you compliments and make you feel good. I didn’t even tell you that I didn’t have an orgasm not even one time. I didn’t want to hurt your feelings. And I thought that in time I would teach you how to bring me to that point.
Maybe the interracial thing was too much for you, or maybe you met someone else. I even thought you felt I was getting too close to you. Whatever the issue, you really should have told me. I think we built enough rapport for that expectation.
I guess i just wanted some sense if closure. I had been dating others while we dated, and I continue to date, but I was hoping to get closer to you. But I remember when I met you, you told me you’re always a woman’s second or third choice. At the time I thought you meant it as if you didn’t prefer to be in second place. But I understand now that you don’t want to be the first one.
All that is cool. Thanks for a fun summer. I just wish my last memory of you didn’t include you prematurely ejaculating, and farting all night.
Take care,
And I wish you success in life.”
Thanks for reading! And stay tuned this weekend for my update on my date with Lola. I really have high hopes for this one. So much so I’m going a little “outside the box” for this one.

Update: Why do we always have to have “The Talk”?

I told you things would dramatically shift gears once the new school year started. And I haven’t even started my college class schedule yet. Yes, I’m about 40 and I’ll explain how that all works later, but not now. So I figured I owed you guys an update, and today would be as good of a day as any.

Things with Krystal are going well. I can’t say they’re progressing, because this type of relationship isn’t really going anywhere. It’s not like some day in the near future she is going to be someone I’m going to introduce to my family as my girlfriend, or eventually make my fiance or wife. We talk every day (texting or actual phone calls).

Today was about the third time we’ve been together in person. Today was one of those times where it was all about the sex. It went a little quicker than expected, but not because of any shortcomings on my end. She had a little embarrassing condition that she apparently didn’t realize until we had already started. It became such a distraction for her (long before I even realized it) that she started incessantly rambling on about it. It was kind of getting annoying and killing the mood.

She opted to finish things orally so we could bring this “embarrassing” situation to an end. She even nearly snuck out the door while I was cleaning up because she was that embarrassed. We talked about the fact that it was normal, I wasn’t freaked out about it, I would call her and want to see her again.

But something she mentioned after she left has really stuck with me. Basically she’s concerned about me finding and being with someone else while I’m seeing her. As she puts it, she “doesn’t like to share.” This kind of struck me funny. She’s married – happily, as she puts it – and frequents a swingers club, and is looking for friends-with-benefits. All of these indicators point to me being someone who has to be OK with “sharing” and I don’t mind – in this particular situation – because I know what it’s all about. I know what I’ve got myself into, and that’s fine.

However, I don’t understand how that translates to me not being able to see other people. I totally get her feelings that once I start an intimate physical relationship with another girl that she doesn’t want to share. Then again, if I was at the point with a girl where I would be ready to begin an intimate relationship, I would definitely end the relationship with Krystal first. There is no way I would try to start a relationship with a new girlfriend with my swinging side-piece in my back pocket. That’s just not right.

But as soon as I started to question what she meant about the whole “sharing” thing, she shut it down, saying she was just being emotional because she recently changed some medication she was taking and was adjusting to it. Red flag??

Inception occurred.  The thought about having “The Talk” began to grow in my brain like a fertilized egg splitting cells until it becomes an embryo. And when that happens, that’s when you need to have “The Talk.” My philosophy has always been; once you have the thought that you should have “The Talk,” that’s when you should have “The Talk.” Don’t wait for some sign from god, or some major event that pushes you over the edge to talk about whatever it is that’s on your mind. It’s the same advice I tell people when they ask me about having “The Talk.” If you have the conversation early, there is always a chance to remedy the situation before it becomes a point of no return.  And the longer you wait, the more you will push it off and procrastinate until you are faced with a situation where you are backed into a corner and have to fight your way out. That leaves only one outcome, blood, guts and a bad breakup.

I need to get this straightened out now before things get any more involved. And this weekend has been interesting. I’ve had a major family function this weekend and not been as readily available to talk and text. So of course, I get the messages asking if I’m mad at her, if she said something or did something to upset me, and all that business.  She wants to meet tomorrow for coffee as a first attempt to “make up” for the other day.

I’m going to meet her, but I’m not as into it as I would’ve been a few days ago. She has been a little clingy this weekend, which is a bit of a turnoff, regardless of the situation and circumstances. And remember when I said that with my luck, the minute I started things off with Krystal, a relationship-worthy girl would present herself. I’m not saying that has exactly happened, but I have been talking with another girl and things are going well.

I definitely want to start dating this new girl, Lola, but we haven’t got to a point where we’ve actually set a time for a first date. It will most likely be this weekend (if at all). So I definitely need to get things straightened out with Krystal beforehand.

In a normal situation, I’m not even talking to other girls once we’ve been on a few dates and especially after having sex. But this isn’t a normal situation. In this particular situation, I’m a side-piece, and not a paid side-piece, so exclusivity is kind of a foggy no-man’s-land. Hence, the reason for “The Talk.”

Even though I despise “The Talk,” I guess it’s inevitable in every relationship. Just as inevitable as that first time you go into the bathroom after your boyfriend/girlfriend and they didn’t use the air freshener. You know it’s coming one day, you just hope it isn’t that bad when it does.

I’ll let you know how it goes. Thanks for reading. And have a great week dating out there!

The Experiment continues, we go swinging for the fences (pt. 2)

OK, just remember you all asked for the sequel to my last post. I really hope I can do this story justice.

I left off after we decided to get together this weekend for some fun, dancing, drinking, and other such shenanigans. Then this story took off like my typical driver shot off the tee at the golf course. I thought I crushed it and it looked pretty – straight, strong and true – then at the apex of its flight, you see the turn signal blinking right before it takes a sharp left hand turn into the rough or the water. Something that looked so promising ends up totally different from I expected. So with that…

I told you Krystal’s husband knew about me and was OK with me, because he has his girls on the side. They’re very open about things like that. So open about it, they are members of the local swingers club.

We were kicking around ideas about what we were going to do Saturday night; everything from a movie to going dancing and all sorts of options in between. But she couldn’t decide.

In the meantime, she’s telling me how she’s been talking to this guy who wants to swing with her and her husband (of course his wife is included in the deal). She doesn’t like this guy, doesn’t want to be with him, and he’s trying to convince them to go to the swingers club Saturday. She’s getting mad because apparently this guy is rather dominant over his wife (and rather abusive as well) and she’s really not digging how he’s talking to her or his wife. So she is totally set against going to the club with them this weekend, or anytime.

Finally, it’s Saturday afternoon and we still haven’t decided on what to do. She is planning on meeting me at my house about 7 p.m. and we’ll figure something out from there. Right at 7 p.m. I get the phone call, “How would you like to go with us to the swingers club?”

My first reaction is to freak out a bit. Not because it’s a swingers club, because I’ve been to a couple in my day – not what you think, it’s a whole different story, if you really want to know, I’ll tell you offline – but because it’s our first real date, I haven’t personally met her husband yet and even though she says he’s cool with me, I’m going to show up at the swingers club and all that entails and expect everything to be cool? Not so sure. But I play it cool and say I’d meet them there.

She sends me the instructions on how to get there. And trust me when I say this place is a nondescript old warehouse out on the edge of town practically in the middle of nowhere. It’s at the end of a long dirt road that winds through the trees with no lights until you round the corner and see the yellow lights of the parking lot. I seriously was waiting to hear dueling banjos playing on the wind.

Krystal said it was a t-shirt and jeans type of place. I was a little more dressed up than that because the other similar clubs I’ve been to were more fancy types of places – suit or sport coat. When I got there, she was right. Jeans everywhere, and coolers. I had not idea this was a BYOB establishment. OK, my expectations were being shattered left and right.

I met them at the front door. It was Krystal and her husband Ken, and Ken’s co-worker Aaron and his wife Jennifer. This was Aaron and Jennifer’s first time at a club like this. Ken is a bit taller than me and a little bigger. He’s an amateur MMA fighter when he’s not working construction. Aaron is kind of  an average looking Joe – not fat, but not fit either, but his wife Jennifer was hot – way hotter than you would expect to be with him.

I hit it off with everybody right away. I’m just easy like that. Ken was really cool about it all and showed us around the club. We took a booth right off the dance floor, and then he showed us the lounges and the private rooms (do I need to explain what these are for?). So we sat down in the main room at our booth and broke out the drinks. I stuck to the rum & cokes, the other guys had beer, the girls started off with grapefruit & vodka (oh my, talk about gross), but they soon switched to the rum & cokes.

Let me paint a picture for you. It is corset night. Most of the women are wearing some sort of corset or bustier. The average age in this room is easily 40 if not higher. It is definitely an older crowd, most of them in their 50s to 60s. Some women were classy about their attire, while others sported the more risqué “convertible corset” which let the boobs hang out exposed to the world. Others were wearing nearly nothing, and what was there was hanging on for dear life with fishing line, tape or magic. While the guys were in jeans, and regular shirts, nothing fancy or dressy. I might have been the best dressed guy there.

We had a great time. Ken and I were talking like two guys hanging out at a football game together. Aaron was included too, but he was a little distracted worrying about the other guys “vulturing” his wife. His wife was hot, did I mention that? She was clearly in the top 5% of women there. Then again she was only 28, quite possibly the youngest one there.

Most of the night, Ken was the 5th wheel. Krystal was all over me, which became easier to handle as the night went on, and Aaron and Jennifer were hanging onto each other for dear life. Finally Ken’s girl showed up. This isn’t his normal, regular girlfriend. This is another girl he’s been hanging around with recently. Krystal is not a big fan of hers – because she’s cute with a small body and she sees her as competition. It was apparent. So much so, that Krystal hooked him up with the wife I mentioned earlier who was married to the real dominating guy (but he didn’t show up at the club that night). And when I say hooked up, yes I mean they went to one of the rooms and got it on. This girl was NOT attractive at all. By my standards, maybe a 4. I won’t get into details, but I would never hook up with her.

So Krystal thinks things are good, girl # 2 (Sarah) is apparently out of the picture, or so she thought. The night is winding down, the girls have been dancing together, and us guys were just sitting around talking about girls (other ones that were there, too) and drinking and having a merry old time. A little while later, we’re all sitting in the booth, and Krystal slides a condom into my pocket and says for me to follow her.

We make our way to a back room and she puts me down on the couch before shutting and locking the door. Things progress pretty quickly – as you can imagine they have to with other people waiting. But you really don’t want to get completely naked in a place like that because you have no idea what went on in that room right before you. Things were going real good – I mean real good. But then she heard some people talking loudly outside the door and we both heard someone mention Krystal’s name and saying something about hurrying it up. So we decided to wrap things up at that point, but by no means were either of us “finished” but we had been in there a while.

Once we got dressed and opened the door, there standing right in the doorway was Ken and Sarah (girl #2). Let’s just say that didn’t go over very well with Krystal. I tried to defuse the situation, with a light “you two kids have fun” comment. We went back to our booth and waited for a while. We danced and talked. But then she pulled Jennifer aside and they talked for a while, then she finally decided to go stop Ken and Sarah in the room. But they were done by the time she got back there. Cutting to the end, it was a source of contention between them (Ken and Krystal) for the rest of the night that he still ended up hooking up with Sarah. I spent most of the night hanging out with Aaron and Jennifer, even coaxing Jennifer out the dance floor a few times. You thought I was going to say I coaxed her into a back room, didn’t you? I thought about it. Ha!

Overall, the night ended well. Ken was still real cool with me, we all went our separate ways, and the next day I talked to her like everything was cool. She still wants to see me more. Can you blame her? I’m irresistible. And Ken is still cool with me. Apparently I get brought up in conversations at home and he asks when I’m hanging out them next. That part is still real hard for me to get used to. I’ve been the “other guy” before, but the main guy never knew about me, and sometimes I didn’t even know about him. This is way different.

There is so much more I could tell here, but this is already my longest post by far. If you want to know more, just ask me, I’ll tell you whatever you want to know (except real life names and places). And as my luck would have it, no sooner do I go out with her, and my Match and other profiles started blowing up on Sunday. Go figure. It’s just my luck.

Stay tuned for more. Thanks for reading.

NSA, FWB, NSFW, This is gonna be interesting (pt 1)

OK, just remember, you asked!

I told you earlier this week that we were taking this dating thing in a whole new different direction. Well, it doesn’t get much “different” than this. OK, I’m sure it could, but I like to keep things reasonable.

As I was debating how dating would change once my son returned home and school started, I kind of did a mental checklist of what my options were. I don’t have the standard every-other-weekend visitation schedule with my ex-wife, my son is with me about 90% of the time, I don’t have ready babysitting options (i.e. family or friends) nearby who could watch him, I have an unpredictable schedule of availability, and I don’t like mixing my children and dates too soon, especially not having them spend the night with my son here. That has made traditional dating pretty tough so far. My largest chunk of free time is during the weekdays when my son is at school because I have a few days free when I am not taking classes myself.

Kicking these things around, an ex of mine joked around that I should “whore (my)self out to the older housewives” in our area, which is rather affluent, as a way to meet my “needs”, make some money and please some local housewives. As interesting as that sounds, I don’t feel like going to jail – ever. So that’s out. Sorry to disappoint all of you that thought that was my big news.

Although my inner Deuce Bigelow was disappointed, it got me to thinking. Maybe there was something, more legal, I could do to address my “dating” needs that would fit my criteria. And let’s be honest, the chances of me meeting, dating and nurturing that special kind of woman on my schedule is about as likely as a teenager working at McDonalds affording the payments on a 2013 Chevy Corvette convertible.

So accepting that, yet not resigning myself to a life of solitude and abstinence, I thought, “where can you find older women, who have time during the day, that are just looking to have fun and not get serious?” Hello, Ashley Madison!

I’m not going to give a full-fledged review of Ashley Madison, yet. I can do that at another time. But it is a little expensive to get access to paid member services. It is pointless to really try any sort of “dating” site for free. So I did the minimum just to give it a try. And so far, in one week I’ve had as much, if not more, success than I did with eHarmony in 6 months.

A girl contacted me early on – OK, lots of girls contacted me initially, but this was the only real, legitimate girl – and we started talking. Things started off real well. She’s a stay-at-home mom that works as an in-home nurse during the week, which means she makes her own hours and schedule. She has an open relationship with her husband who has a regular girlfriend, plus others on the side, and she just wants somebody to have fun with. A FWB (friends with benefits) relationship where she can have fun, but isn’t looking for a man to replace her husband. It’s also a NSA (no, not THAT NSA, a no strings attached) arrangement, which means I would be open to explore other options with other women if the opportunities arise. Like I said earlier, knowing my luck, this is when that Real Special Lady will show herself. Go figure. So stay tuned for that mess.

So Krystal decided to meet me for coffee this afternoon. When we got together, she was cute dressed up in her scrubs, as she was in between seeing patients, and very nervous. It took a while to get her comfortable, normally I’m the shy, nervous one. We talked about her relationship with her husband, his girlfriends, how bored she is at home, and that she had already told him about me. That was a little awkward, but I took it in stride. She generally has a constant “boyfriend” on the side, just as her husband has his steady girlfriend.  So it’s not like this is anything new to them.

Things went really well. It was so much more fun without all the normal pressures you feel during a regular date. OK, that’s just coming from a guy’s perspective. I can only imagine what pressures girls deal with on first dates, so I can only guess. We also agreed to see each other again and go out tomorrow night.

Let’s just say things get a lot more weird and interesting from there. But we will include that when I update you all on that date later. I have to save something interesting to keep coming back for more.

Until then … Thank you for reading and stay tuned for all of the fun (or at least I hope it’s fun).