Dating After 40: Do Any of Us Really Know What We Are Doing?

The raining of men as Miranda refers to it as halted some here since the big day on Tuesday. Feast or Famine I suppose…not sure what to think about Mr. Diver. He was ALL into me on Monday…lots of emailing, texting, call me kind of thing. Then, we were supposed to go out Monday night and he got called into work (which I think was legit). He started texting me again after he got back Monday night saying that he might just drive up anyway, but he had to work Tuesday morning so we finally decided to just reschedule. I sent him a text saying “Hi” Wednesday and we arranged to go out tonight BUT it’s now 1pm my time and I haven’t heard anything from him…so now I can’t go or I’ll seem too available, damn it. It’s also possible he googled me and found out that I’m still technically married with a kid. I guess the world of cyber stalking can go both ways. We hadn’t  discussed  the details of our lives yet. He went straight for the date before dropping off, so he doesn’t know abou...

On Monday, I finally caved and agreed to see The Inmate after work. He only had an hour (which is the main reason I agreed to this) between the time we both got off work and the time he had to be back at the halfway house – every time I write ‘halfway house’ I literally laugh out loud at myself. So he met me at my house and we sat outside on my front porch and talked. I wouldn’t let him come inside – and I’m sure you’re all thinking “But Gwyn, this isn’t safe. He’s an ex-convict and now he knows where you live.” I thought about that too but you have to realize that this is a guy who dated one of my best friends for over 5 years, I know him fairly well and he has never done anything to make me scared of him in the least. It’s not like he was in jail for a violent crime – he used to move a lot of cocaine. I’m not saying that makes him a good person I’m just saying he’s not the only cocaine dealer I know or have known (but let me make one thing very clear, I have NEVER and will NEVER do...

So I never made a big announcement but about a week ago, I decided it was time to end things with Sawyer. I know I mentioned that the last time we were together (about 2 weeks ago) if felt like the end was nigh. Well I decided that I was tired of playing his games and that there were too many other fish in the proverbial sea to keep myself tied to him. Plus I figured we’d been in this “relationship” for almost 6 months without getting caught and surely our luck would run out soon. So the last time he was over, I had planned to “break up” with him but I admit I don’t like confrontation and I decided to take the wimpy way out and just stop pursing him. Last Monday I only emailed him a couple times and that was simply because I was excited about my upcoming trip to Hawaii. We didn’t talk other than that and I certainly was avoiding contacting him no matter how much I wanted to. Bad habits are hard to break! The weekend passed and this Monday who popped up emailing me like crazy…...

The second date with Crossfit is officially over. Here’s a recap: I got to his house at about 9:30pm Tuesday night, he came outside to meet me at my car and gave me a kiss when he saw me. I was slightly confused when I pulled up to his house because it was REALLY big and in a very nice neighborhood – more on that later (I think I’ve found myself a rich boy). He looked hot, he’s one of those guys who can make cargo shorts and a fitted t-shirt look ridiculously sexy. We walked inside and he gave me a little tour of the crib….aquarium, wet bar, kitchen, six bedrooms, his Cockapoo, hot tub, etc. I quickly realized that this was his parents’ house. Oh my Lord I’m at his parents’ house. Perfect. I asked him who he lived with, he said his parents and told me he thought we had talked about that before (NO we did not). Ends up there is a good explanation for this – he was in the process of buying a new condo and his stepmom had to co-sign for him because his personal training business is only...

After weeks, nay months, of Facebook chatting and texting, College Crush (AKA suspected Pillsbury Doughboy) finally asked me out. Though as his typical MO it was a wee bit vague. He and I text just about every day and it varies from just friendly chit chat to deep life altering conversations to fun & flirty. Let me give you some back story. College Crush (CC) was a boy I obviously had a crush on back in the day at school. We were friends but my much less confident self was never brave enough to ask him out. He was in a frat, though not the typical frat guy, and a bit of a party boy so I mostly just hoped we’d run into each other at a club one night when I had enough liquid courage to flirt with him outright. When I had finally worked up the courage (without the alcohol), I happened to start dating another guy so friends is all we ever were. Randomly we ran into each other a time or two over the next 10 years but we never really kept in touch until Facebook – cue the dram...

Yesterday was a busy day! Owen came over in the morning (finally). About 10 minutes before he was to arrive though, Gavin calls. He leaves a message (because I didn’t answer) inviting me over for coffee…which means he was sitting on his back porch looking at my house having coffee…uh-oh. I quick texted Miranda with a WTF?!. Then, he calls again as Owen is pulling into my driveway. He left another message about wanting to hang out before he had to go to work. Owen comes in and we have some smoking hot sex, as always. OMG I’ve never, ever met a man that enjoys pleasuring me the way this one does…I mean most men like it when a girl cums a lot but Owen freaking gets off on doing it to me over and over and over again. It’s still the BEST sex ever…hands down. He will literally do anything I tell him to do and he does it so well! Afterwards in the shower (because it ALWAYS requires a shower), he starts asking me questions about my divorce. This is weird because remember when he started oversh...

So I had a chat with a friend the other day that left me a little unsettled.  Apparently, over the last few months with all the changes in my life she felt like she didn’t know me anymore.  That we didn’t have much in common these days.  I think more than anything it was just a time/distance issue and perhaps a little slackness on both of our behalves on keeping in touch.  But, it still got me to thinking. I’ve had many a person tell me that getting divorced really changes your friendships.  That some of your friends will suddenly become distant either to concerns about the strength of their own marriages or because they suddenly see you as some sort of competition.  That some friends will find themselves unable to connect with you because they view your life as so very different from theirs.  Also, some friends will suddenly be envious of your freedom and that will put a chink in your relationship.  (Please note – I don’t think any of these t...

So just a quick Crossfit update: I texted him yesterday afternoon to say hello and that started a brief texting flurry until he had to train a client. During the texting he asked me my plans for the night…..mentioned use of a hot tub….offered a back massage….tried to bribe me with wine…all to no avail. At this point it was almost 9:30pm and I wasn’t driving an hour on a week night to go and see him – eight pack or not. Miranda was very impressed with my willpower as she was urging me to hit the road! After he got done with his last client he called me and again asked if I wanted to come visit (not using those exact words but being a little more subtle). I told him I wanted to but it just wasn’t in the cards for tonight, I was tired and already in bed. He seemed a little dejected at this news and basically said “Well ok if you’re not going to drive here then I guess I will just see you next week when I get back from my trip.” Again, not his exact words but you get the picture. He told...

Something's happening here....what it is ain't exactly clear...but I think I'm being watched. I hardly got out of the car good tonight upon arriving home when what should happen? My phone rings with a strange number. I answered it b/c it was a Hawaii number and I've applied for some new jobs...you never know who could be calling. (You also never know who you have deleted from your cell, but they kept your number either...always a crapshoot.) Anyway, I answer and it's Gavin. He's calling me from a friend's phone b/c his battery is dead. He wants to know if I want to hang out. Um, not really...first of all, I don't want to "hang out" with him anymore. Fuck him, why yes I will, thank you...hang out...not so much. Second, I know how this thing with him and the gf goes...on today, off tomorrow. If I'm just fucking him, I could care less if they are on or off...irrelevant. If I'm "hanging out" with him, I might get a little pissy if...

So last night was my first date with Crossfit. I got all purdy for him – wore a slightly form fitting (but not fancy) black dress with some cute wedges. My makeup, done by my gay glamour fairy, was perfect. Very natural (I usually don’t wear any) but definitely sexy. The only kink in my armor was a very attractive, cleat-mark shaped bruise on the outside of my upper thigh from my soccer game. Nobody’s perfect! He came to pick me up about 7:15 and my roommate proceeded to interrogate him while I waited upstairs. My gay bff asked him a few questions as well and then came upstairs to get me. When he came up he gushed and gushed about how cute Crossfit was, how he shook his hand and introduced himself was and how I had hit the jackpot. That did nothing to help my nerves. I have dated some very attractive guys in the past but the body on this man is literally one of the best I’ve seen. Intimidating is an understatement. Anyways, my gay bff gave me $60 cash for emergencies (he’s sort of li...

So just a quick post, us ladies have been blowing up the blog today! LOL! I’m having a bit of a manic Monday to tell the truth. I obviously had a wonderful weekend with FJB and came in still riding that high. Then Motorcycle Man had some kind of temper tantrum that I’m still scratching my head over. We’re Facebook friends and I noticed that some random redneck looking girl in a saloon girl shirt had put on his page “I had a great weekend babe. Thank you!” Now of course there’s no commitment here but I still thought that was a little weird considering he and I tried to schedule a date for this weekend but we couldn’t connect. And I fully know and admit that I totally blew him off on Saturday so I could see FJB with the good old “I have a friend coming to town” line but still. I felt irrationally jealous I admit. He’s been teasing me for a while (maybe it’s not so teasing after all though) that I have a boyfriend because of my availability. And yes, some of my scheduling is...

Boys boys everywhere. I don’t know what to do with myself. Let me give you the latest man-team updates. First, Army Boy is officially off the team. He got a DUI last Thursday, totaled his bike and ended up spending the night in the emergency room. I think it’s safe to say this little soldier has a drinking problem and I want nothing to do with it. I haven’t communicated with him at all since he told me about the DUI and I think he’s gotten the hint. So that was Thursday…..on Friday I woke up to a message on Facebook from an old college fling. By old college fling I mean a guy I had sex with a few times, one of those times being while he was dating my friend. I hadn’t heard from him since we were about 21 or so and found it odd that he sent me a random message at 2:45am. I agreed to give him my phone number so we started texting. I found out why I hadn’t heard from him in awhile – he’s been in prison!!!! I didn’t ask details but he told me it was for ‘drugs and guns’. Now, don’t get...

Wow, the kitty is not behaving right now...yet I'm kind of digging it. Remember I told you guys on Tuesday about walking into Gavin's, getting some, and walking out? It really wasn't great, but the idea of hot neighbor sex is well, pretty hot. Yeah...it's ON. I was walking with my grandfather today and I saw his gf leaving. When I walked into the back door of my house approximately 2.5 minutes later, he'd left a message. I didn't call back since there was a very full house here this morning. He called again about 30 minutes later (as is his MO...he'll blow a phone up until you answer)...still couldn't talk and I missed that call because I was in the shower. So, I actually called him back tonight after I put Chloe to bed because I'd had some wine and the kitty was doing my thinking. He came over, we had some dirty hot sex right here at this computer desk watching porn, and then over on my bed. It was SO much better tonight than it was Tuesday. For sta...

My grandparents who have been married for 58 years left today apparently feeling that their mission had failed. My grandparents came with an agenda. It was to "teach" us that marriage is hell. My grandmother actually said this sentence last night in context to something she told my cousin about being a military wife a few weeks ago. "Marriage is not meant to make you happy." - The Ya-Ya ROFL...she's serious too. She told me that I'm not being sensible. My grandfather took me on a walk today and told me that a girl needs her father and that when Russell gets promoted, I should follow him because I can do my Masters program anywhere and Chloe needs her dad around. Yikes... No other real news...Gavin called this morning repeatedly, but the fam was here so no playtime even if I'd wanted it. Owen is trying to line up Tuesday. If he doesn't pull this Tuesday out, he may have to be placed on restriction. I posted a new ad on CL this week...several promisi...

So many things to blog about, where to start and what to focus on. I’m gonna focus on my 2nd date with Fake Jewish Boy (FJB). We went out again last night and had the best time. We had planned to go eat and then go watch some amateur stock car racing. It was a different date to say the least but you gotta give FJB credit for coming up with something other than the traditional dinner/movie date. Unfortunately the weather was not cooperating as much as we’d have liked. We got to the race and it was drizzling and walked up to the gates only to hear that they were cancelling the race due to the weather. As we walked, he very smoothly and sweetly took my hand. Girly sigh….I love holding hands. We checked out the stadium and stood in the drizzle for a few minutes sort of cuddled up some. Standing next to a tall guy is so freaking hot. I had intentionally not worn heels just to see the real difference in our heights. I’m 5’7 and he’s 6’3. Delicious to lean on a tall guy like that ...

So last night was my date with Fake Jewish Boy (FJB) and it rocked! I had a little trepidation about the date because even though we’ve talked a ridiculous amount in the last few days, I know he’s like a super smarty-pants and he comes across as super sarcastic. But I was still game because the online chemistry has been popping. So after a mad dash shopping effort at lunch time, I headed home a wee bit early to freshen up and figure out what in the hell to wear. When he asked me out, FJB actually had a plan for the date, which earned him major points. We were meeting at a local mini-golf/arcade place to kill off the initial nerves and then we were heading out for dinner. So I had to figure out the whole how short of a skirt, how booby of a shirt can I wear combo that wouldn’t be totally revealing and slutty considering the venue. As I was trying on various outfits, who should call – the disappearing Lawyer Boy. I haven’t said much about him lately because there really hasn’t ...

I would like to dedicate today’s post to Truck Driver and his baby arm (aka penis for those of you who don’t get my slang). So Truck Driver isn’t a big guy, he’s about 5’10 and I’d say he wears about a size 34 pants – which are baggy on him – and neither his feet or hands are unusually large. Not that this is a secret, but us women are always trying to use context clues to figure out how big a guy’s package is. Either that or we just try to accidentally brush up against it. Judging by his height and size I just wasn’t sure what I was getting myself into. The first night we hung out there was no physical contact. We were both sort of uncomfortable and I could tell he didn’t want to freak me out by trying anything smooth. Through some flirty texting after that night, I let him know that it was ok for him to make a move. We ended up doing the deed two Sundays ago at about 11am or so - he said he wanted to work me out before I went to my soccer game and of course I obliged. In fact the w...

The other day Miranda and I were discussing the members of our respective man-teams and realized something that they all (or almost all) have in common. They are all packing....in more ways than one. First we have Motorcycle Man. On his first date with Miranda he said he had a concealed weapons permit and carried a gun with him at all times. She didn’t believe him. On the second date, once they arrived at MM’s house the first thing he did was pull his gun out of the console of his truck – along with the two empty beer cans he had guzzled on the way home. That was only the beginning. He then took Miranda on a gun tour and showed her all his weapons. Two are in the kitchen and two are in his bedroom, one of those underneath his pillow. Next is Lawyer Boy. Who knew a metrosexual could have such a manly side? Think Miami Vice circa 2010. Miranda asked him if he had a gun and he replied “Yes, do you want to see it?” They went into the bedroom and as Miranda sat on the bed he started p...

Rounding out the squad are a few third-string players including a transplant from Spain with horrible grammar and a very cute personal trainer who jumps out of airplanes. At this point I am only in the messaging stage with these two. But, if things with Truck Driver don’t end up going well I’m calling in the subs. The personal trainer has a super hot body and he plays soccer (I’m a soccer freak of sorts, still play every weekend and talk more crap than anybody on the field). Both score him points. I’ve never dated a trainer, though I’ve fantasized about my personal trainer more times than I can count, and I’m slightly intimidated at the thought of it. I’m in decent shape and workout a lot but I have also been known to consume an entire bag of Rolos in one sitting. His last message to me ended with “So, do have a busy week this week?” I’m guessing in the next message he’s going to ask me out. I don’t really know what I will say to that at this point. I’m down with dating different guy...

OMG today was just a weird, fucked up day. The universe is not right and if it is then I'm screwed b/c it hated me today. You guys know about the AM...no Owen, Gavin instead. Craziness... Oh but the day got better (and by that I mean worse)after I got home from Gavin's. I cleaned the house in prep for guests and then decided to go on a run. As I was stretching, I get a text from Russell about his car not starting. I'm freaking about this because we're trying to move and buy furniture and stuff and we really don't have the money for car repairs right now...seriously. So, he calls AAA and they come out and tell him it's probably his key. Say what?? He texts me to ask if I can bring him my key (like right then). No, no I can't. I have to drive around the island a bazillion times today thanks to his crappy work schedule. My afternoon went like this...took friend to airport, drove to Russell's car, my key worked, took him my key, went back to airport to pic...

Bad, bad, bad kitty...the brain knows better, but sometimes the kitty has a mind of her own. I got up this morning and went out on the porch to have breakfast with Russell before he went to see his boy toy and then onto work. As I'm sitting on the porch eating breakfast, I can see Gavin's house. I would like to point out before I go too much further into this tale that I know his gf was there this morning because I could see her. I'm not sure why I feel the need to point it out, as it does NOT make me look like a better person in this story...but I'll go for honesty at this stage in the game. Russell leaves the house...Owen texts saying he doesn't know what's up today...he's not sure he can get away. I'm kind of pissed with him about this because hello, it's Tuesday. Tuesdays are Owen-Jules sex days. And then the phone rings and it's Gavin and I answer it...why, oh why? The kitty is bad, that's why. He asks if I want to come hang out. I repl...

I’ve been following this blog for a few months now, ever since Miranda let me in on her gig. We work together and I’m glad to say that Miranda trusts me enough to share the details of her ‘secret life.’ Little did I know that we share some of the same secrets. No, I’m not married and I’m not technically involved in any sort of infidelity. But that doesn’t mean I’m not mixed up in a whole bunch of crazy! I’m a 29-year old single professional girl, own my own home and car and have managed to take care of myself relatively well. Ok…ok…grandma still helps me out every now and again but who am I to stop her? (you can learn more about grandma if you click on the “Bling Bling Ya’ll” link under Miranda and Jules’ blogroll) About two years ago I ended a 6-year relationship with the person I thought I was going to marry. If I were writing this blog back then, there would be much more infidelity to be discussed. Since the breakup I’ve entered the dating world and, most recently, the online da...

So I knew me going to Hawaii would be an issue for Duckie. I emailed him a very polite request talking about day camp for Leo this summer with an “oh by the way” note I’ll be on vacation this one week and asking if he could keep the kids an extra night or two. I figured it was just a matter of time before he’d want to know where I was going exactly. I got an email back asking me to call him. So I sucked it up and called him tonight. He wanted to know where I was going and I coyly said I was just taking a little trip. He persisted in asking where I was going so I said casually I was going to go see Jules. After a moment, he said isn’t that you friend in Hawaii? LOL. I said yes and I could see the steam coming out of his ears through the phone. He asked how I could afford the trip since money was so tight. Which I am being careful but the truth is I have more disposable income now than I did living with him. Weird I know but that’s how the money is working out. Of course a...

I'm bored...I've been in a funk...I need to get out of it. I've only seen Owen once this month, but he's on the schedule for tomorrow. We both have a lot of stuff coming up though with company and his 3 week vacation. I'm really hoping my version of Texas makes his way back out this summer, but that's months away. I'm so not wanting to go there with Damien. Gavin called me Friday night to say that he thinks about me "quite often", but honestly I think that's asking for trouble in a big time way. I need some fresh meat. My new boy toy was supposed to get back onto this island last night. I haven't heard from him yet today though, although to his credit I think he's just worked that last 2 weeks straight. Anyway, it's time to find a new one that is single, straight, and employed...all of which seems a tall order on this rock. -Jules

Just had to share - I just booked my tickets to fly out and see Jules at the end of June. Hawaii may never be the same! Miranda

So there’s a potential new boy on the Miranda team. He who shall be known as Faux-Jew Boy. Why this distinction? Well his first, middle, and last name are very Jewish. Btu in conversation last night, he revealed that he grew up in a pretty traditional church. Weird. Maybe his dad’s Jewish? Sounds like his parents aren’t together anymore but I didn’t get that far in to specifics with him. We had been exchanging emails here and there through Pof but nothing was progressing past that point then out of the blue he emailed me the other day and asked for my number and suggested we meet. I said I was up for it and gave him the digits. Nothing. Like 3-4 days went by with no text or call so I just figured whatever. Then yesterday as I was pulling into church, yes despite all my sinful ways I do attend church on a fairly regular basis LOL, he texted me asking if I wanted to go to a baseball game in an hour. Yes, in exactly one hour from the time he texted me. I was perplexed. I want...

So I spent a lovely country evening with Motorcycle Man last night. We went riding for a while and then hit up the local grocery store to get some food for dinner. He was grilling out for me. The bike ride was awesome. Nothing like riding on the back of a motorcycle with a hot guy. He’s going to take me on a long ride soon up to the mountains. I can’t wait for that. It’s going to be so beautiful. At the grocery store, we were cracking up and being obnoxious and people kept staring at us. Hopefully they were looking at us with envy for seeming like such a cool, fun couple, not because they were thinking look at that young girl with that old man. LOL. Then we headed back to his house and just hung out drinking some beers while he cooked. Guys should so cook for girls more often. It’s hot! Afterwards we had a very tame evening mostly because I had to pick up the kids in the morning and didn’t want to be hung-over while on mom duty for a change. We were lying on the overly man-s...