Daphne: Ruh roh, Raggy! Get the Mystery Machine (Rewind)

Background: Daphne contact me via Match and after checking out her profile, I figured it couldn’t hurt to talk to her and see what happened. We seemed to have a lot of common interests and the email conversations went very well. But I would have to admit the clincher was her height. She was 5’11” and I’m a sucker for tall women. She was fairly attractive, but her height intrigued me enough to allow me to let something like that not influence me as much.

She was a huge baseball fan, which is always bonus points for me, and a hockey fan. We would chat and text through baseball games and the hockey playoffs talking about the games, as well as other miscellaneous things. The connection was good, but not overwhelming like some others have been. She was a nurse and worked out with a personal trainer three times a week. So, maybe my expectations were a little high. We decided to get to drinks one night at a local bar in our area.

The Date: I got to the bar about 5-10 minutes before she did and grabbed a table with a clear view of the front door, so I could see her when she came in and she would be able to find me easily. We were playfully texting as she was pulling in, and I said I had to confess that I wasn’t a tall guy, that I was actually short and balding. She didn’t buy it.

But my jaw dropped when she entered the bar. I recognized her face, barely, but she was not what her pictures led me to believe. I understood she was not a petite girl, especially since she was almost 6-feet tall. That was OK with me. But the girl who walked in was twice the size of any picture she had posted on her profile. She noticed me almost as soon as I noticed her. If she wouldn’t have, I might have considered sneaking out. I have never run out on a date before, but I really thought about it this time.

I had already ordered drinks, and they arrived just as she arrived at the table. We exchanged hellos, but no hugs or anything. I don’t know if she ever caught the look on my face when I first noticed her, and I really hope she didn’t. Apparently the thought of wondering how to deal with the situation made me rather nervous.

When I get nervous on a bad date, I talk and talk and talk. Maybe it is because I am hoping something bad comes out of my mouth that turns her off, maybe it is because I was to try to rush through all of the possible topics as fast as I can in the hope that the date might end sooner, or maybe I just would rather dominate the conversation and hope nothing meaningful is exchanged.  We, or I should say I, talked about all sorts of random things and did a lot of people-watching and commenting on other people in the bar.

Her size never came up. I wanted to ask about her seeing a trainer three times a week because I wasn’t exactly sure what they accomplished, other than making her bigger. And overall I felt rather deceived. She looked nothing like her pictures, they were likely a few years old. And when that happens, I automatically feel a level of distrust because I feel like I have been lied to and manipulated just for a date.

When it finally came time for me to leave, because I had to go pick up my son, we exchanged a friendly hug goodbye after I walked her to her car. There was no kiss or any other physical contact. I am not sure if she sensed my lack of a connection with her, but I am pretty sure she figured out things didn’t go well.

Post date: After the date, I never heard from her again, nor did I try to contact her either. There was no connection, and I am usually more lenient about physical appearances, but this was just way too far outside my comfort zone.  I know it may sound shallow and superficial, but we all know there must be a physical attraction and connection as well as the other connections. Plus, like I said, it really felt a bit dishonest that she represented herself with pictures that were obviously older, and stated she was tall and athletic and toned. I have a hard time getting over initial deceptions like that.

Grade: D

Justine: The Yoga instructor with a New York state of mind

Background: Justine had a very sarcastic and sassy profile on Match that really caught my attention and made me laugh. We followed the normal Match email-to-text progression, but followed that up with numerous phone conversations. The phone conversations proved to enhance the connection exponentially as we got to know each other.

Oddly enough, part of our initial conversations included talking about issues we were having with other online dating members and our bad experiences. We discussed what ended up being the end of my courtship of Georgia, as well as her issues with guys who had adopted rather inappropriate or immature approaches to asking for a first date. One guy kept whining that he was certain she was going to cancel their date plans, and his insecurity led to a sort of self-fulfilling prophecy. While another asked her if she was naked (via text) while she was getting ready for their date – which led to her promptly canceling the date. All winners, and apparently weenies, too. But enough about them.

It took a little while longer for us to actually set up an actual date. We both had conflicting dates and schedules, plus she had her children and needed to wait until their next visitation with her ex-husband. The night she was supposed to go out with the naked-comment-guy, but cancelled, I had a follow-up date with Irene. The advantage was that it bought us a few extra days of chatting and talking, which led to a very deep connection that I had not experienced with online dating in a long time.

She is self-employed as a yoga/fitness instructor. She’s about 5’8″ with a very fit body, almost like a bodybuilder’s, and a New Yorker complete with attitude, accent and Mets sticker in the rear window of her SUV.

Things were getting so good that we just had to make time to see each other. The following weekend, we both cleared our respective dance floors (I had pending plans with Irene, she had a few more options – typical).

The Date: We both decided we wanted as much time as possible on this first date. So we decided to do lunch together and then hit an amusement park. I know it sounds like an unconventional first-date, but we both like amusement parks – and the faster and crazier the rides, the better.

However, our lunch date turned out to be more of a late lunch date. We had been up talking until the wee hours of the morning for the last few days, and we were both rather worn out and tired. Her more than me. We’re not as young as we used to be. Since we were both dragging, I told her to just let me know when she was ready and we would meet. Finally we decided to meet about 2 p.m. at a trendy burger joint (not fast food). It was in her part of town and about a 30-minute drive for me. I arrived on time and when I texted her that I was there, she let me know she still wasn’t ready. Our nerves were frazzled as it was, and her running behind started to create a bit of doubt about her commitment to the date. Especially after witnessing her ability to cancel dates at the last minute with little provocation. So, I was very calm about her running behind. She was very apologetic and repeatedly mentioned how nervous she was about meeting me.

About 30 minutes later she showed up. When we finally met, she literally jumped into my arms. I guess that was a good sign.

At lunch we split a specialty burger because neither one of us wanted to be too full before we went riding amusement park rides. The conversation went very well and she was very conversational with everyone around us. She’s definitely a social butterfly. After eating we headed to the park.

She had a season pass to the amusement park and takes her kids there often. While I was purchasing my own pass into, she proceeded to buy us both VIP passes that gave us front-of-the-line access to all the rides. Yes, it was rather expensive, so I didn’t have time to intercede and offer to pay for them (as any gentleman should on a first date). I think she already figured that out and that is why she did it that way. However, I made sure I paid for all of the snacks we had while at the park.

We made sure we made the most of the VIP passes and hit all the major rides, and even hit some of our favorites several times. With each passing moment, we got more and more comfortable. We started holding hands and getting real close to each other while waiting for rides. She even put a very playful smooch on me while waiting in line for her favorite ride. (Later on she would confess she wished she wouldn’t have done that because she wanted the first kiss to be my idea and something a little more romantic.) We decided to call it a day as evening started to set in and she began to get tired.

On the way out of the park, we both said we were hungry. We decided to stop for Chinese food on the way back to her house because she wanted to relax and watch a movie together. After getting back to her house, we ate and settled in to watch the movie. I had no idea she was a fan of baseball movies ((bonus points)), so we watched “42” the new movie about Jackie Robinson.

As the movie started, I moved in for a real kiss attempt and it was a success. So much so that we were distracted several times during the movie to make out. I don’t think she objected too much considering she initiated as much as I did. Nothing else happened and I was home before midnight. So all-in-all, it was a success.

Post date: Since then we have continued to bond and talk. She invited me over again to hang out before she went to work and it appears we are both settling in for what might actually become a relationship. But we will see. These things have blown up in my face before. ((Remember Georgia?))

Grade: A

Make the first time about her, you will be rewarded over & over again

This is for all the guys out there who happen to read this – Listen up!!

It is very apparent women are very dissatisfied with the effort they are getting from the men they date. How do I know this? I listen to them.

That’s Tip #1. Listen! It’s so stinking simple, yet so many guys think they are witty enough, good-looking enough, or rich enough (gag!) to skate by without really listening to what their date has to say. We all know the “cliché” that women want a guy who actually listens to them. But it’s more than that. They want a guy who listens to them, but who will also take what they have heard and use that information to treat them the way they want their men to treat them. Because generally they are complaining about past relationships and what went wrong. Take that information, use it and don’t make the same stupid mistakes. Some guys aren’t getting the memo.

I’m getting a little sidetracked here, but the point is, if you listen, what I am about to tell you will be so much easier.

Tip #2 (it’s almost tip #1, but without #1 there is no #2): When presented with the rare and precious opportunity of that first sexual experience – make it ALL about her!!

Most guys, when presented with the opportunity, regardless of how long it took them to get there – 2 dates or 2 months – get so excited at the sight of boobs and a naked woman, they give into their animal urges and turn it into a Discovery Channel episode. News flash: she wants the love scene from The Notebook, not Mating Practices of African Wildebeests.

Now if you have been paying attention to what she has been telling you, I’m pretty sure she has hinted at what she disliked during past physical relationships. For example, I had a girl tell me all she wanted from her man was for him to just take control and just have his way with her sometimes (memo noted), and some other simple things that I could NOT believe her past boyfriends did not do for her, that were basic practice for me. It seemed too easy.

But when that moment comes, bury every selfish urge you have to dominate her and finish the race first. This is the one time when finishing first will cost you the race. Make it all about her!!

Caress her, lightly running your fingertips all over her body. Don’t just start groping at her breasts, gently tickle them around the nipples almost teasing her. Everything needs to be gentle and sensuous. Hit all the sensual erogenous zones (nape of the neck, ear lobes, soft sides of the breasts, a few inches below the bellybutton, the insides of her thighs, etc.). Work your way from the ear lobes down.

If she gives you a distinct sign she really enjoys something, like sucking on or play-biting her nipples, linger there for a while before moving on. And make sure you are paying attention to her body language so you know what she likes, what she REALLY likes, and what she doesn’t like. It will make things so much easier. Don’t ruin it all by missing the cue she doesn’t like something. End, obviously, with the oral sex. Make sure it is soft and gentle. It’s not like licking a bunch of stamps. Think of it more like kissing. Keep it soft, sensual, know when and how to use the tongue, and most importantly, vary the speed and intensity. Sometimes you want to go fast and light, other times you want slow with more pressure. There are some good resources to help teach you the best ways to please a woman “down there”, but my best advice is to watch some lesbian pornos. Watch and learn. Or just ask your woman what she wants.

Do NOT let her start “working” on you until she has at least one orgasm. If you can manage it, try to keep as much of your clothing on as possible and maximize her number of orgasms before getting your turn. It is almost my personal guarantee, that if you can do this, she will undress you faster than you have ever seen before in your life. She will take care of you with a passion and vigor you never would have seen otherwise.

But best of all, she will REMEMBER it and think about it – and think about it some more. And the next time she has the chance to have sex with you, you will receive carryover from the first time and it will be another vigorous round of love-making. But don’t stop pleasing her! I can’t stress that enough. Just because you took care of her the first time, doesn’t mean your work is done. You have to keep taking care of her needs.

My first rule of sex is to make sure she gets off first. There are very few exceptions to this rule, but some do exist and most of them hinge on her controlling the situation. If you can do that, AND listen to what she tells you before, during and after sex, you will never lose her because your sex life is bad. She may leave you for other reasons, but the bedroom game won’t be one of them.

But so many men are so selfish they screw it all up. If you don’t believe there’s any truth to what I’m saying, have your woman read this. But be careful, I am not responsible for what she does after that. And I have no idea how she got my phone number.

Good luck!

Ellen: Beautiful blonde, but maybe a bit of baggage (Rewind)

Background: She contacted me on Match with an email sounding like she was interested in me but that because of my job and her job, there might be a conflict of interest to where she wouldn’t be able to date me. I responded back clarifying the issues and it actually started a line of communication that opened us up to a potential date. There were lots of things she wanted us to do together; karaoke, go to the gun range, go horseback riding together, etc. So we decided on meeting for lunch one afternoon while she was traveling about town for her job. She was a financial consultant who worked from home, so her car was basically her office.

The only potential red flag to this point was the stalker behavior of her ex-fiance. While we were emailing, texting and talking, there were several instances where he would stalk her at Wal-Mart, or mess with her animals while she was away from the house. She has a ranch with horses and other farm animals. Yes, she’s quite country. The kind of girl who likes pickup trucks over regular cars. I tried not to let that all get in the way because everyone has issues, a little drama, and things they can’t control in their life.

The Date: We met for lunch on a Wednesday at a popular italian restaurant chain. There was a car accident two blocks from the restaurant, so my normal practice of being the first one there was thwarted. So when I arrived she was sitting in the lobby finishing up some work while she waited. She was absolutely beautiful. Natural curly blonde hair, fit but not muscular, about 5’10” in heels wearing a short, sleeveless dress. She big round eyes and large, teeth-bearing smile. Very attractive.

Since she was clearly attractive and looked even better than her profile pictures, I was definitely interested and went for the introductory hug. I don’t shake hands with a girl on a date, that just seems so cold and impersonal. She did not display any hesitation or recoil during the hug and actually seemed to reciprocate. She had an excellent ice breaker that really seemed to ease any nerves that were lingering. After the hug, the fist thing she said was “Wow, you’re short!” Considering I am well over 6-feet tall, that surely wasn’t the case. I feigned being wounded by the comment to play along, and it definitely got us both laughing.

The conversation went well during the meal, with plenty of laughs and no awkward moments. We covered the basics, sharing a bit about our pasts and kids, and such. Her husband was killed in a car accident before her 7-year-old son was born, and later she got engaged to another guy and they bought a house together. Things fell apart and she kicked him out, keeping the ranch house. But the ranch is a bit much for a single mom to manage alone, so she has lots of random help stopping by to assist. This wouldn’t be any sort of issue, except apparently it’s nothing but locals offering to help to get into her house and ask for dates. She claimed it really bugged her sometimes, but I got the sense she really liked all the attention.

We had a hard end-time for the date because she had to leave to make appointments with other clients. As we walked out, she commented on how good I smelled (which is normally a pretty good sign). I walked her to her car and we exchanged another hug goodbye. I didn’t attempt a kiss because I really liked this girl and was a bit nervous about messing it up with a possibly unwanted advance on the first date. We also made (tentative) plans for another date on Saturday, and she was going to find a babysitter for her son. She left for her appointments and everything seemed to be going well. I even got a nice text only minutes after she left.

Post date: Our conversations remained the same the rest of the week. No sign of any changes or anything. The only thing was that neither one of us mentioned the date on Saturday. I did not want to seem like I was pressing the issue, and was letting her handle it. However, on Friday, when I had not heard anything regarding plans for Saturday, I asked about them. That is when she just casually said she wasn’t able to find a babysitter.

The problem with that is I would have hoped for a little courtesy informing me of this at some point instead of waiting to the last-minute. Sure I could have brought up our Saturday plans earlier in the week, but something tells me that wouldn’t have made a difference. And when I asked about rescheduling, she was very non-committal about setting up another time. I started to get the distinct impression that she just made the date to avoid confrontation and had every intention to cancel. Maybe I’m wrong, but I’m pretty sure I’m not.

We talked daily, like usual, for another few days before the conversation started to tail off. Then it was reduced to her returning simple replies to my texts. She would not initiate conversations and her responses were very short, direct responses and she never would ask me questions or get into full-fledged conversations. So I decided to stop communicating altogether to see her response. I’ve heard from her very very rarely. And it’s just a very vanilla “how are you doing?” type of thing that lasts about 4-6 texts before it’s over.

However, if a second chance ever presented itself, I’d definitely take it. She was a very sweet, smart, grounded and beautiful girl. How could I pass that up?

Grade: B+

Fiona: She really works out, but it didn’t work out (Rewind)

Background: Another Match date that had a quick connection with us going from Match emails to texting to dating in a relatively quick fashion. Part of that seems to be the trend of girls on the site wanting to get right to that in-person event to see if there is any connection there. There seems to be a lot of connections that are made via emails that fizzle out in person. It makes sense. These quick turnaround dates also seem to favor simple happy hour or lunch get-togethers to limit the amount of time of the first, possibly awkward, encounter. So we decided to meet at a popular happy hour bar not too far from her work.

The Date: We met at the bar for some drinks and snacks. I was only a few minutes late because I had to drive almost completely to the other side of town right in the middle of rush hour. So, the odds were against me. We started off talking at the bar and then moved upstairs onto the roof where they have more tables and a bar.

She was very beautiful in her summer dress with her hair in a pony tail because she worked out in the gym over lunch. She was about 5’9″ in heels.

She works out more than most men and has the body of a bodybuilder without actually lifting competitively. She is about 120 lbs of muscle and is very sexy about showing it off. She shared several pictures showing off her back and legs muscles, while also showing me her tattoos.

The conversation went well, though I was a little more shy than usual. I was so concerned about impressing her that it actually caused me to seem nervous around her. But I wasn’t I really enjoyed being around her. There definitely seemed to be some sort of chemistry and we started talking about making other plans. The date came to an end because she said she had to be home when her son got home from his after school job. I walked her to her car and we had a good, meaningful hug goodnight.

Post date: We talked regularly and the date didn’t seem to change our talking habits or our chemistry. She was however obsessed with asking me to send pictures of my “junk”, which I never did because it just seemed creepy. I tried to play it into something suggestive by saying if she really wanted to see it, she just needed to let me know when and where to meet her and she could see it. It never went anywhere, nor did I expect it to.

Then I went out of town one weekend. While away, I was planning to visit some high school friends that Friday night, and she said she had plans with high school friends too. We playfully talked about drunk dialing each other later in the night and having fun together on the phone. As it turned out, I didn’t go out that night because plans changed. I texted her that I was staying in, but didn’t hear anything back from her.

The next morning I woke up and saw that I had a text message from her – timestamped about 2:45am. Saying that she had met someone and wanted to see where it went, and that we couldn’t talk anymore.

My advice is to tell someone you’re not going to see them anymore BEFORE you hookup with someone else, not immediately after. Just saying.

So that was it. Until a few weeks later ….

Grade: B

UPDATE: Georgia, Fiona, Irene and introducing Justine

What a busy week. We’ve all heard the saying “when it rains it pours.” It’s no different in dating. Dating has its droughts, but it also has its floods. This is one of those times when there is almost too much going on at one time to keep it all straight, and enjoy it. We’re looking in the face of five first dates in the last couple of weeks, not to mention follow-up dates with several of them. So let’s get to the updates.

GEORGIA: She had lots of potential. We started talking like a couple and had a great time together. I was just on the verge of turning off all of the other candidates because it looked like things were going to get exclusive. But after a great night out, which ended with her proposing watching a movie at her house, things changed. We cuddled on the couch watching the movie, with intermittent kissing sessions, until about 2am. There was no sex, and I didn’t broach the subject. She had some recent issues with men forcing themselves on her, so I was taking it real slow with her. I texted her when I got home and her response was that she was looking forward to spending a lot more time together.

Then things flipped 180 degrees. I hardly heard from her the next day and she ignored most of my messages. I wrote it off that she was busy spending time with her kids, but I was starting to get nervous. Then on Monday, the same thing, she ignored most of my messages and I hardly heard from her and when I would ask it everything was OK she would say everything was fine and I had nothing to worry about.

You can never fully trust that, because women will tell you everything is perfectly fine and you have nothing to worry about right up until the moment when they drop the big bomb on you.

I tried calling that night and she said she wasn’t able to talk because she had a lot of work to do that night, but that everything was OK. Then the next day, I decided to stop texting until she texted me first. Then oddly enough, I got advice – from a woman you will meet later (Justine) – saying I should just text her to say HI and see what’s up. So I did. That’s when the bomb dropped. She said she wanted to be honest and let me know she really wasn’t ready to be dating again yet, and that she felt sorry for leading me on. Sometimes, I really hate being right. My gut was telling me the whole time that she was getting scared. I just responded that I was sorry to hear that. So … moving on …

FIONA: Then the craziest thing happened. I heard from Fiona again. It had been a couple of weeks since I last heard from her when she told me she was going to focus on her new relationship with this cop she met. So out of the blue I get a message asking how I was doing. I said fine, but I was a little confused because I didn’t think I was going to hear from her again. She had the nerve to ask me “Why?” Why?? Because you said so, that’s why.

We talked briefly about her being happier than she has been in a long time with this guy and she wanted to still be friends. I was OK with it, though it sounded kind of odd because we had a good time together but didn’t thing we were that close otherwise she probably would have been focusing on me and not seeing other guys. And I already replayed the entire conversation to make sure I didn’t miss any hints that she was looking to see if I was still interested in her. Well, considering the fact I flat out asked her if she was still seeing this guy (perfect opportunity to say “no” and see my reaction), she responded that she was and was very happy. So if it was a gauge to try to get me back, it wasn’t a very good one. But then, just as fast as she came back into the scene, she was gone again and I haven’t heard from her since. Go figure.

IRENE: I’ve seen Irene a couple more times and things are trending to possibility of making a bonafide relationship. She even invited me over and made me dinner. The chemistry is good all around. We’ve even talked about going out again this weekend.

But the problem is Justine. We’ve been talking for a while now and have a crazy cool connection. Texting all day, talking all night – sometimes for up to 3 hours until 2am. There is definitely chemistry there. So we’ve been trying to find time to get together for a real date and want to spend time together this weekend.

The problem comes with what to do with Irene. You never truly really knows what is going to happen with two people who have great chemistry emailing and texting that meet for the first time. Many times there is no physical chemistry and it falls flat. So in the event that happens, I want to keep options open with Irene.

Thanks for reading and expect to see the post from time with Justine sometime by the end of the weekend. Thanks for reading.

Irene: Tall and blonde with all the right curves

Background: Another Match date which progressed faster than many other dates. We emailed briefly on the site, and transitioned to texting rather quickly. I find I like moving on to texting and calling much faster now. Emailing through dating sites just seems so cold and takes forever. Match email can take as long s 30 minutes from the time it is sent to the time the recipient is notified, but I’m getting sidetracked.

There was definitely a good connection and her pictures were very nice and she looked very attractive. This, however, caused a bit of concern because there have been too many times where I got burned with people looking a bit different than their pictures lead you to believe. The date came up on a spur of the moment suggestion after an early night with my friends. I was texting Irene all night and she was getting ready for bed. When she heard I was heading home early she asked if I wanted to get together, and I was definitely OK with it. So she got out of bed, put her make up on and got ready in a matter of 15-20 minutes. A definite bonus that she was willing to do that to meet with me for only a few hours.

The Date: Since it was approaching 11pm when we met, we just decided to meet at a bar located between us and have drinks and talk. She showed up less than 5 minutes after I did and it was easy to recognize her when she walked in. She was tall (but not taller than me), blonde and curvy. The good kind of curvy, not the fat kind of curvy. Apparently there are two definitions to what that means on dating sites. I’ve learned that the hard way. But she looked great – even with her hair in a ponytail (a nice one this time).

The conversation went smooth and fast. We were both laughing and there weren’t any awkward silences or moments.  We covered all sorts of topics, from jobs and ex’s to dating and what we were looking for from our dates. The connection we had emailing and texting definitely carried over throughout the date.

We closed down the bar and I walked her to her car. The conversation was still going and was still good. At her car, she was clearly not in a hurry to get in and go. So after a few more minutes of conversation, I moved in for the good night kiss. Even the kiss had a connection with it. It was good and prolonged, and after we stopped and talked a bit more, she moved in for more. So I think it was well received.

Post date: We texted each other when we got home and have continued texting and talking since. A follow-up date is definitely in the future, unless things with Georgia get too serious (but that is a dilemma for another post).

Grade: A