Wanda Update: We Escaped the Room but Not the Monsoon

I hate when I waste my best stuff on a dead end.

OK, to be fair, I had no idea it was (going to be) a dead end when I planned my second date with Wanda, nor did I think it was a dead end as it was all happening. This is my hindsight talking.

But Date 2 with Wanda started off swimmingly (sarcasm meter is beeping). The sitter was 10 minutes late, it was a 30-40 minute drive to begin with, then for some reason all the leisurely drivers were all on the road at the same time in my way cruising along at 65 in the FAST lane. Argh! Seriously??

Well, I got where we were meeting about 20 minutes later than planned, but still in plenty of time for our activity. Wanda was sitting on a bench, killing time on her phone. As I approached, I playfully said she looked like she was waiting for someone. She responded she was. So I asked if I could join her while she waited, and she said Yes. As I sat down next to her, I put my arm around her and kind of leaned in a bit (to gauge where she was at tonight). Nothing (1). She stood up and I followed her. I moved closer to see if a hug or anything was an option. Nope (2). So I asked if she was ready for this, she said Yes, so I extended my hand to hold hands as we walked. Again, Nothing (3).

We walked a few blocks to an old warehouse. A few times during the week, she had asked what we were doing, and I refused to tip my hand. I just told her where to meet me, and wanted to keep it a surprise. I booked us in one of the Breakout or Escape rooms, where you get locked in a room for an hour and have to solve the puzzles in order to find the code to get out. Neither one of us had done it before and it sounded really fun. It was also a diabolical plan to see how well we can work together, communicate, deal with a (moderately) stressful situation, and have fun at the same time. We were teamed up with a group of 6 other people who worked together.

It took us nearly the entire hour, but we managed to solve the riddles and get out before time expired. It was really fun.

While we were waiting to start, we had to sign waivers. While I was signing my waiver, the girl at the counter was asking Wanda if she’d ever done this before. She told her she hadn’t and that this was a surprise, etc. The girl behind the counter was gushing how cool and how sweet it all was. Then when Wanda went to the bathroom, the girl asked me a bunch more questions about our date night and thought it was cool. So when Wanda came back, she was gushing even more about our night. I don’t think I could’ve planned that better, even I would have paid the girl to say those things. It was definitely big bonus points in my favor (or at least should’ve been).

While we were waiting, and during other various points of the night, I tried getting close to her, even putting my arm around her in a half-hug at one point, but it all seemed to fail or not be reciprocated. (4-9) After we finished, I went to offer to hold her hand again as we walked to the restaurant. More Nothing (10). I didn’t say anything or act put-off by it. I just rolled with it.

The place at which we ate, was rather pricey, but we each ordered the chicken and quinoa and a glass of wine. We talked about all sorts or random things. So I tried to bring up some future events I had going on, like when my son was gone to gauge her interest of doing something then. Didn’t bite. (11) I noticed on her Facebook page that she had mentioned going to see something at the theater that I also wanted to see, so I brought that up. She’s going the weekend before me with her friends, and has her kids the weekend I have tickets. No “Oh, I wish I would’ve known, I would’ve loved to go with you.” or “maybe we’ll do something else while your son is gone.” Nothing. (12)

Then the monsoon hit. Ok it wasn’t a monsoon – we don’t live on the coast – but it sure looked, felt and sounded like one. Remember the whole “Duck” thing? And the radar looked ominous. THe hostess at the restaurant came around from table to table showing everyone – it looked BAD.

So, since Wanda had to drive and hour (plus) to get home, I suggested we should probably wrap things up early so she can get somewhere safe before it gets worse. She decided to stay in town with her friend (that I mentioned she routinely stays with) instead of going all the way home. In no way was I going to offer her coming to my place. That didn’t seem right.  So we called the night a little early – something I did not want to do, but felt it was the right thing. Also, as you can see, lots of warning signs were popping up, so it wasn’t like calling it early was going to kill any mood or chances.

Look, at the breakout room and as we were talking about other ideas I had had for the night, she was always making it work related. “Oh, we had talked about that at work, and I thought we should do that as a team exercise,” or “I really wanted to check that place out to see if we could hold an event there. How many people do you think it holds?” Stuff like that. Look, I don’t mind talking about work, but I want my date present there with me, in the moment. Not me planning her next work outings for her. It was like she was more focused on that than me. And then we were talking about the charity functions she has going on this weekend. Now this certain pair or group of guys always comes up in discussions about their plans. Going to baseball games, and one of the guys texting her “hey, what about me?” and stuff like that. Well, these same guys (I don’t know if they are friends, co-workers, married, single, nothing) came up in conversation last night. One of the guys set something up for them at the first charity event and said she “owed” him. So she was saying, “Fine, I’ll hold your drink for you when you go to the bathroom,” or “Fine, I’ll hold your hand if some girl tries to flirt with you.” SMH, WTF?? Why are you talking about holding some other guy’s hand when you won’t even hold mine? Got it, aye aye, message received, Captain! Moving on …

As we left I offered to get my car and pick her up at the door and drive her to her car. Like I said, it was a torrential downpour outside. She passed. She insisted on walking the block and a half to her car. So I walked her to her car. We got to her car and she put her stuff inside. She turned and gave me a very strong, lingering hug. I thought, “Ok, there was no first date kiss, so this is my last chance.” You never get the first kiss on date three, that’s like unheard of. But the moment the lingering hug lightened up, she spun and ducked in her car before I could even think about making a move. (what are we on, 13 now?) I mean I was intended to try at the beginning of the date, and now this. Stuck out.

She did the standard “I’ll let you know when I get there, and let me know when you get home,” thing. She texted me promptly when she got to her friend’s. She said she had a fun (complete with smiley face 🙂  ). I asked if she wanted to do it (go out) again, no response (14). And then I didn’t hear from her all night.

After contemplating where things are going with this, I finally texted her again this morning to say “good morning” and to see if she was home yet because I knew she had early appointments back home. She said she was back home, at work, and would call me later. I’m not sure I like the “tone” of that. Maybe she’s going to tell me she definitely wants to see me again and that she really is interested in me. But I’m not holding my breath for that. Remember, I’m trusting my gut again, and it isn’t telling me any good news right now.

Look, I like her, I really do. But together, there’s little chemistry. She’s not flirty (not even texting or on the phone), lord knows I’ve tried to pull it out of her. No takers. She’s not affectionate. I’ve tried that too. She’s also not very “talkative”. I don’t hear much from her. Especially compared to other girls who have been clearly interested in me. If she’s interested in me, she has a funny way of showing it.  But I’m guessing, and planning on, that she’s just not that into me. Which is totally fine. It’s not the end of the world.

It was a long distance long shot anyway. I gave it a shot. I’ll keep you updated. And as always, thanks for reading.

Staci Update: Hot and Heavy but not quite a Home Run yet

Time is quickly running out on my Summer Vacation. My son returns in just under two weeks, which is going to put a serious halt to my spontaneity, as well as my ability to see Staci on a regular basis. We’ve had several discussions about it, it almost seems like a daily thing, because it is really log-jammed in my brain.

I guess it’s mainly just my insecurity creeping through,  but my concern is that she’ll realize it’s not worth it to try and maintain a relationship with me while having to deal with my ridiculous schedule. She insists it won’t be a problem, and when I look at it logically, I’m sure she’s right. We really only see each other once, maybe twice per week as it is – and that’s with me having my open schedule right now. Between spending time with her family (her father, brother and sister all live in the area) and friends, as well as giving her time to do what she needs to do around the house, it’s not like we’ve been seeing each other every day or anything.

The only problem is that once my son returns, we will have to be more deliberate and schedule time together. But again, that’s not a huge change from what we do already. The big change will be on my end having to find someone to watch my son on our date nights. Especially since it is still going to be a while before we start incorporating Staci into events with my son, we will have to set up specific date nights and I’ll have to set up a regular babysitter for that time.

The issue with that is me getting over my guilt. I have a tendency to feel guilty doing things, buying things or taking time for myself. I know I need to take time for myself – all the post-divorce books say so, my friends and family say so, and even Staci says so. I just need to work on it myself.

On with the update …

Things have been going really good. Since last I updated you (when she tried to get me to hang out with her friend), we went to the concert she really wanted to see, last week. Since it was such a big deal for her, I did a little extra work and spent a little extra money to make sure we had excellent seats (within the first ten rows). It was a great night, and she was all over me all night,

I very much like the fact that she is not hesitant about showing her affection for me in public; holding hands, arms around each other, holding each other, and kissing each other – not just pecks, but serious kisses. She initiates it just as much as I do, which is even better.

The next “small leap for man, one giant leap for me” came this weekend. Staci wanted to take me shopping to refresh my wardrobe. My closet definitely needs an update, but I’m a guy, I hate shopping for clothes. To me, if it fits and is comfortable, I don’t see a reason to change.

She said I “already look hot, but would look super hot” with some newer clothes. So I gave her a few hundred dollars and told her to go nuts. We spent about 4+ hours shopping. Though I hate shopping, it was a fun spending that much time with her, and to say there was a lot of flirting is an understatement. She was always wanting me to turn around so she could see my butt in jeans and shorts. She said she really wanted to see me in some specific clothes, and I said I wanted to try on the clothes that she wanted to see me out of. That’s when she rebutted with “Doesn’t that mean the same thing?” And watching her face when I try certain things on was very rewarding and encouraging.

She even joked (how much was joking and how much might be serious is up for debate) that after this (meaning shopping for new clothes) that I would drop her like a bad habit because I would have more/better options available to me now that I would look better going out. Ya, I don’t see that happening. But it was sweet to say.

The only time we disagreed on a purchase was when she wanted to me to get a pair of rather plain khaki shorts. I thought they looked a little simple, and made me look like an old golfer. She loved them on me and insisted and insisted that I get them. So ultimately I said what mattered most what was what she thought about it, not what I thought. If she liked it that much, and it registered on the “Hot and Bothered” meter (which was referenced numerous times during the day – by her), then I might as well get them and wear them sometime when we’re together. I won’t wear them any other time. But I compromised. Ha!

After a long day of shopping, we went back to her house to get ready to go out to dinner with Jack and Amy. I showered while she picked out clothes for me to wear. No, she didn’t pick out the khaki shorts. Once I was ready, and waiting for her, I crashed on her bed for a while because I was exhausted. When she was ready to go, she came out, and instead of sitting on the bed next to me – as I fully expected – she got on top of me straddling & kissing me. Nothing serious happened, except for a few minutes of kissing, before we had to head to the restaurant.

We met Jack and Amy at a Mexican restaurant. Not the best I’ve been to, but it was OK. I mainly drank my dinner anyway, having several fruit-infused margaritas. After dinner, we went to a nearby bar for a few drinks before heading back to Staci’s house.

That is when things got serious. Once we started going, it got very hot and heavy. To the point where she said she was very forward, aggressively saying things like she wanted me to stick my tongue in her mouth (not that wasn’t happening already), to use my tongue on her more, and at one point she grabbed the waist of my shorts with both hands like she was about to undo them saying “I want these off of you.” But shortly after that, when I suggested heading upstairs (to her bedroom), she backed away and stopped saying she wasn’t ready for that, yet. That break happened about halfway through the entire session together, and we continued on for quite a while after that, just not pushing it further, though she was still pressing and rubbing her hip or upper thigh up against my crotch so she could “feel me”.

I am not sure what is exactly going on with her “not being ready, yet” but I am also not pressing the issue. Clearly all the major signs are there, but whatever that final obstacle is – I don’t know. I’m not sure if she’s just scared because it’s been so long since her last time, she’s just insecure about her body, she wants to make sure I’m in it for the long haul and just not in it for the sex, or if she’s waiting for some sort of “I love you” moment where she’s certain she feels that way about me and/or I feel that way about her. I don’t know, maybe it’s something else altogether. I don’t want to get pessimistic here, but I’ve seen instances where a cheating woman – married or in a relationship – will back off just short of sex, because to her that would be cheating. Not the seeing, kissing and making out with other men – clearly. I don’t think that’s the case here, but that’s the dark, pessimistic side creeping through.

Honestly, I’m really hoping it gets resolved within the next week or so, because I really don’t want to have this still up in the air and unresolved when my son is here. But again, if it doesn’t, it won’t be a deal-breaker or anything.

Even the time in between seeing each other is getting much better. She’s calling more, texting more without me texting first, opening up a lot more when she talks/texts. Even this morning she called right as I was getting up because she wanted to talk to me as she was driving into work. She’s also interested in a lot of other aspects of my life, offering suggestions and encouragement, and making sure I follow through on things. I can’t say I’ve had someone looking after me like that in any relationship I’ve been in over the last 10-15 years.

But it still has it’s moments where I wonder if she’s really interested or not. But again, that could just be the pessimism of relationships past creeping in. I could probably write a whole post on all the negative, pessimistic thoughts I get every once in a while. If you want to hear the dark side, let me know.

Well, that should be enough for today. Not that I put a cap on length, but we’ve crossed the 1500-word mark. I’ll definitely post more, don’t worry. And as always, thanks for reading!

Staci Update: Weekend road trip was great, despite no sex

Let’s just get it out of the way, just like I said in the headline, there was no sex this weekend on our first road trip together.

I know the general consensus was that it was almost a certainty to happen, but the fact that it didn’t doesn’t really bother me very much because the weekend was still exceptionally great.

Don’t get me wrong, it was a minor kick in the Ego that things didn’t get more physical. But it wasn’t from lack of effort, I tried – boy did I try, but I didn’t push the issue or make a big deal about it when my progressive advancements were blocked aside like a hockey goalie.

But again, to emphasize, it was still a great weekend!

Last I left off, Staci mentioned the issue of us staying together in the hotel room. I had arranged for her to be able to bring her dog, who is under medication for some issues for which she just took her to the vet. And we both took our dogs with us.

On the car ride, conversations about my dog, what she was going to do during the day while I spent the day with my son until we needed to leave for the concert, etc., led to me to believe that us staying together was not really an issue any more.

Sleeping arrangements were, as expected, in separate beds. But she did – both nights and both mornings, come lay with me, snuggle and even make out for a while. And like I said, I definitely tried to progress things, but once things seemed to get to a certain point, she would come up with an excuse to do something else (like take a shower) or go back to her bed. I didn’t make a big deal about it, nor did I try to force the issue.

She clearly wants to take things – especially in that department – slow. Though, she was all about kissing and holding hands on the first date, which is actually faster than I would normally have progressed things. I am totally fine with it, as long as the relationship as a whole continues to progress forward.

We had numerous good conversations, including her perspective on some of the “issues” that I claimed I usually have in relationships, and she attributed it to them (other girls) being immature, insecure and generally more needy. She even made the comment that I’ve “been dating girls, when (I) need to date a woman.” She even expounded on how that would make me even better, and she would “expect me to step up my game” and would help with that.

The entire weekend was very intimate and affectionate. She was just as eager to initiate contact, holding, kissing, etc., whether we were alone, at the concert, or even in public.

The concert itself was great. She was latched on to or pressed up against me the entire time. However, at the end she started to feel feel faint and had to leave. The concert was outside and was very hot and humid. As she left to go sit down somewhere to the side, she said she didn’t want me to miss the end of the concert (which was just entering the encore portion). There was no way I was letting her go off somewhere alone while she wasn’t feeling good, so I followed her and stayed by her and watched the rest of the show from the side.

When the show was over, she wanted to head inside the building near the venue to get in the air conditioning while I went to find my friends that I left when going after her. We met up again shortly after by the main entrance and she was feeling a lot better. We had planned to go out for some drinks after the concert, but my friend and his girlfriend – who we rode the concert with – bailed and said they were just going to head back home.

This is where I made my mistake. Probably.

All night, things had seemingly been progressing to the inevitable climax of sex. But it was only a little after 11pm and I know she tends to prefer to hang out later than that. So I suggested going to a bar near the hotel. We went there for another 1-2 hours drinking, playing games, talking … having a good time. But when we got back to the room, she basically crashed. She took her dog outside, came back, got ready for bed and almost immediately went to bed.

Maybe I missed my window, I’m not sure. I can’t say for certain that things would have gone differently if we would’ve just gone straight back to the room instead of going out again. Did she see that as a sign I wasn’t interested? Would things have still worked out the same – ending with no sex – regardless? I don’t know, maybe, but I just have that lingering doubt in my mind that it might have been different.

Heading home was just as good, affectionate, intimate, and productive as the rest of the weekend. Lots of talking and sharing, etc. When I dropped her off at home, I lingered for a while and she seemed to be in no hurry to get rid of me. More “making out” took place, but that was it. We definitely seem to enjoy being intimate with each other. I’ve felt when a girl just tolerates making out, kissing, etc., just to avoid an uncomfortable situation. This is NOT that. Clearly!

I am definitely flirty with her and she responds to it, just as I’d hope, and even reciprocates. I also make sure to tell her how I feel about her and what I’m thinking, so there isn’t any confusion about what my intentions are. Again, she reciprocates right along with me,

I am very much attracted to her. And she seems attracted to me as well. She says she is, but more importantly, her actions definitely show it.

For as good as the weekend was, I wouldn’t be doing my job if I didn’t through some negative vibes out there. She is still very hard to read and anticipate. It does make me wonder where this is all going. When we’re together, everything is great! But when we’re apart, I don’t hear from her like I would expect to, she doesn’t say or do things like I would expect her too. It is very hard to read.

Maybe that is just her taking it slow. Maybe that is how a more confident, mature woman does things. Maybe I am used to dealing with clingy, immature “girls” regardless of how old they might be. Then again, maybe I’m not the only one she is seeing or talking to? I don’t think she talks about me to her friends. We haven’t talked about it, but that’s the feeling I get. I definitely haven’t met any of her friends – except the co-workers we met on accident at the baseball game – and have no clue if there is an opportunity coming up or not.

I know that seems like a lot of pessimism, and trust me, I could come up with more if I wanted to. But I’m trying to stay positive. Maybe she just does things differently than I am used to, and that’s the simple answer. Maybe.

But I don’t want to feel like I’m wasting my time with this. As you know, I have a short window to really get to know someone when my son is gone.

I have kind of put my chips All-In here with Staci. It’s getting too late to start something new with anyone else.

But I have to be realistic with myself. So, I’m going to give it another month – until right before my son comes back – to see where it is. Two-plus months of dating (longer if you count the Match courtship) is plenty of time to determine potential commitment, right?!? If things are not more clear, and we haven’t even had sex by then, I don’t see the point in trying to prolong it, knowing the hurdles I will have to cross to make it work after he gets back.

I am more than willing to make the effort once he is back to make it work, as long as I know the commitment and mutual feelings are there.

Hopefully things clear up, get more interesting and more solidified in the next few weeks. Stay tuned, and I promise to keep you all updated.

What do you think? What are your thoughts? What do you think about this weekend not culminating in sex, as most of you expected? Where do you think this is going? How do you read into what I’m seeing? Please share!