The First Date
Welcome back!
(go back to Chapter IV)
Chapter V
There wasn’t much settling back at home before I dropped a hint to Jim that I wanted to meet up. I was tired of keeping the distance. No more covert operations or digging through the trash… time to dive in headfirst and see just how serious this guy can be. I made a comment that I loved the food at Geoffrey’s. He bit. Fast forward – day of the date. We set a time but since I’m always running around like a nut, I was running behind. He texted me when he was heading over. After getting out of the shower and seeing that he was en route, I texted back, “Running late, ah!” Luckily he’s a great guy and took the hint. He responded, “Don’t panic, just text me when you’re ready.” Definitely took the pressure off!
He took me to dinner and to a movie. He was quite the gentleman and honestly, I’ve never been treated so well. He told me I looked beautiful. He held doors for me. He opened the car door when I got in and when I got out. He paid for both the dinner and the movie in such a flash that I didn’t even have a chance to pull out a card. I considered it a date, and I was pretty sure he did, too, but it was never discussed so there is always that doubt in the back of your mind. I was so thrilled and at that point extremely excited since all those signs pointed to it being a date.
When it was obvious to me that it was a date, I yearned for more. A handhold, touch on the arm, hug, kiss… Halfway through the movie I started getting fidgety. Multiple times I told myself, just reach for his hand, dumb ass! But something inside told me to wait. I wanted him to make that move. I wanted him to tell me how he was feeling.
On the way back to the car he says casually, So there’s something I realized I’ve never brought up in all our conversations…” Freeze. “I’ve told you about my most recent break up…” Oh no, what could he possibly tell me? “…but I was actually married right out of high school. We were together for 8 years and then she cheated on me. We were divorced and that’s it.” Swallow. Okay, so it’s not too big of a deal really. Just would have liked to be told this earlier. I told him, “Okay, thanks for telling me. No biggie.” I shrugged it off as a good piece of old news. Mental, phew!
On the way back to my house he asked, “Do you want to stop for a cup of coffee? I don’t want our conversation to end.” Melt! Good, I wouldn’t have to give up on some physical connection just yet. I told him, “Yes, I’d love to have a cup of coffee.” Finally when we sit down and order our coffee, he spills. Not the coffee, his feelings. Halleluiah! He tells me, “I don’t know how you feel about me or if you even considered this a date but I’m really into you and I have been since the first time I met you. If you aren’t into me, then I’ll let it go and we can remain friends but I need to throw it out there or I’ll never forgive myself.” Yes, a man actually said this to me. Jackpot! I told him I felt the same way. That mutual understanding and a kiss at the end of the night sealed the deal. I was dating Jim and I was happy.
to be continued…
Give In to It
Filed under: Advice, Dating, Stories, Tips, Top Lists, Uncategorized
(go back to Chapter III)
Chapter IV
I left for business with only an iPhone in hand. Jim and I stayed in touch over email and through other online mediums thanks to my international data plan. I wished I had an international dating plan but I’d have to just wait it out. It figures that right when he gets the guts to ask me out I am whisked away on some crazy jet setting experience. I wasn’t even sure where anything with Jim would lead but I was sure I was being lead somewhere interesting and I wanted to partake. The emails and correspondence between Jim and I became more flirty and telling. He told me over and over how he missed my presence and how he couldn’t wait for me to return. He made more plans for my return and I told him I looked forward to it. I swear the anticipation that built was unbelievable but fun. I couldn’t wait to spend some time with him. A co-worker even noticed my attitude was different. I denied anything was up but she insisted, “Oh no, you are definitely taken by someone.”
Now, up until this point I had never even physically touched Jim. Although we had a friendship and we had spent time together, I had never even attempted to hug him or touch him in any way and he in turn kept his distance. As I said earlier, I was afraid to go there too early. The next thought that occurred to me was about physical attraction. There was such an emotional and intellectual attraction between Jim and I that I began to doubt there could be anything more. I did doubt my attraction to him. It wasn’t a do you think he’s good looking issue – it was a physical spark I was looking for – fireworks, butterflies, explosions. Is that asking too much? When all these thoughts entered my mind I was suddenly nervous to return. I thought – well maybe if I remain far away forever we can continue this affair of the mind and I’d remain happy. Of course I was delusional and that would never be satisfying. I’d have to face my fear. If you don’t allow yourself to be somewhat vulnerable you’ll never know what you could have. Living in fear means living alone and that is not what we yearn for. So, I jumped on a plane and made my way back home; I was ready to ignite the spark.
to be continued…
The Distance Dance
(go back to Chapter II)
Chapter III
As I realized what was forming between Jim and I we began to do what I call, the distance dance. I wanted to remain further than an arm’s reach away yet I didn’t want him to think I wasn’t interested. This turned into many flirty conversations but nothing overly obvious. There were a few times when he’d compliment me in a way that would both flatter me and make me tilt an eyebrow. He would say I was pretty. He would say I inspired him to work harder. He would say I was one of the most motivated and intelligent woman he’d ever met.
Who wouldn’t be flattered? I didn’t return these compliments for two reasons. I’m not usually the type of person who verbally compliments someone (yes I need to work on that) and I was also unsure of how it would be taken. I had been keeping my physical distance and now I was also keeping my vocal distance. What was I afraid of? Looking back, I was afraid he wasn’t feeling the same way I was feeling. Silly, I know. I was also afraid to get involved with someone who was coming out of a long term relationship. All I knew was that I was intrigued; I wanted to see where things would go. I began to wonder how long this dance would last.
During this time I was also questioning my own feelings. What did I want? Was I really interested in Jim as more than a friend? Where did I see this going? The answers were obvious to me but I wasn’t ready to admit them yet. I have had so many relationships in the past start because I initiated them. I wanted this to be different. I wanted him to approach me. I want to know someone wanted me. I wanted someone to man up and admit it. Okay, flashing neon lights now: Ask me out!
Then Jim asked me to join him at an event (finally!), however, I was simultaneously hit with a business opportunity that meant traveling for some time. I would be gone for a while so any dating plans would have to wait – but was Jim asking me out on a date? I wasn’t so sure. My intuition told me yes but another part of me warned that it might not be a date and not to get my hopes up. I do put my career ahead of anything else, and Jim knows this, so I bought my tickets to head out of town that weekend. The realization that I would be out of contact for a while struck a nerve in me. In the last conversation with Jim before I left town, he told me he would really miss me. I finally gave in and told him I’d miss him as well, because I would. The distance dance would continue a bit longer.
to be continued…
The Friendly Meeting that turns Personal
(go back to Chapter I)
Chapter II
Now there wasn’t one instance where the friendship Jim and I began turned more personal. Over the next few months our lives became more entwined online, in social circles and in personal matters. We were talking and interacting on a daily basis. I learned that Jim had recently been through a break up. That relationship had been a long one – over 5 years. There were similarities between his just-ended relationship and a past long term relationship that I was a part of once upon a time. My thoughts about my experiences helped Jim understand the female perspective a bit more in his current situation.
He told me that he and his ex had lived together for most of their relationship. He also told me he thought they would eventually get married and have kids. In the end she fell out of love and decided to leave. Jim had no idea this was coming. It shocked and stunned him. It took about four weeks of transition (as she moved out) and trips to a therapist to get him to realize that the relationship had been ending for a while. His girlfriend had fallen into that very common comfort zone where she existed only as a half of the equation. She felt that she had lost herself and that the relationship was the cause of her not pursuing her dreams. Jim felt he was always supportive of her. Regardless of Jim’s support, his girlfriend’s thoughts and state of mind were her own worst enemy. Her unhappiness about her life turned into resentment and it ate a hole through the center of their relationship. She also never voiced her fears to Jim – the first rule in a relationship – open and honest communication.
Needless to say the break up was very hard on him and I talked to him about it for many days and nights. I learned more about him through these talks and although he and I became very close, I was careful to remain a supportive friend and not become too involved or invested in what was going on. He needed this time to reflect and heal.
I learned that his past girlfriend was younger than him by quite a few years which I found interesting because it seemed that I was about her same age. I didn’t really know how old Jim was. I thought about asking but didn’t. From other stories about his family I figured he was probably in his mid-thirties. More on that later.
Since he was offering up information about himself, I did so in return. Over these few months we developed a friendship. It was easy to talk to him and easy to ask for advice. I cared about how he was doing, how his career was progressing and invited him a few times to join my friends and I out and about.
Soon our conversations turned into more detailed conversations about relationships, sex, and what it is that we were looking for in a relationship. It was always hypothetical – well verbally hypothetical but I won’t deny the subtext. Although I felt a hint of something else there lurking between the lines, I tried to remain just a friend. If I were being honest with myself, and with you all, I’d have to say I remained on that friend level only because I was weary of his newly ended relationship. But there was something there and I was pretty certain it was mutual.
to be continued…
The Professional Meeting that turns Friendly
An introduction to this story is contained in the previous post.
Chapter I
I’m big into meeting new people, talking shop and helping those people who impress me connect with others. One of those people, Jim, met me for coffee one morning and after sharing business related information we found ourselves talking about our interests, our experiences and our lives. Jolted back to reality by the calendar notification on my phone, I realized our talk lasted two and a half hours. We both ran off to our respective meetings and engagements but we would keep in touch. I left there thinking, wow, I just met someone extremely intelligent, funny, hard working and with similar likes and dislikes to my own – need to keep this one close.
Ready to experience & learn?
I know I’ve been MIA for a bit but it’s because I’ve been in a whirlwind of a situation. I’m back and I’m ready to share. I am excited to tell you all because I think there are lessons to be learned and moments to be remembered. In all relationships, short or long, there are things you need to take away from the experience. If you don’t you will sit in limbo wondering why you are still making the same mistakes, seeing the same types of people, or why you still feel so alone. Grow from your experiences and help others grow as well.
Following this post will be a series of posts about my experience. Be sure to follow in order. I will number them as I go. Chapter I
The Good Breakup
Ethan and I broke up.
Bet you didn’t see that one coming. I know, I’m a bucket o surprises.
There isn’t much to say about it other than things didn’t work out. Oh well, at least I tried. Not really too many hard feelings on either side. We agreed to give each other some space for a while, but we’re back on speaking terms. Regardless of how things ended, we still would have to talk, since he cosigned on a rather large loan for me, which will have to be refinanced in 6 months to get him off the title.
Leave it to me to get legally entrenched with guys that I’m casually dating.
I’m pretty happy with the way that things turned out. He didn’t feel the need to completely cut me out of his life, steal my friends, mail be back gifts I gave him or sell any of my stuff on facebook.
That would be a more typical breakup for me.
Thanks but no thanks
I smell like single. There is no other way to explain how I get asked out by totally random guys as much as I do. At Starbucks pouring my half and half, in line at the DMV, checking out at the supermarket and even one epic incident of a man stopping his car and getting out to ask me for my number on the street.
While very flattering, they’re never even remotely dateable. Ever. For once, I would like the gorgeous man in the pinstripe suit I’ve been eyeing across the room to make his way over and strike up a witty conversation.
Unfortunately, my life doesn’t want to seem to work out that way, so I often find myself in the awkward situation of trying to explain that I don’t ever want to have contact with any of these dudes again.
Most of you ladies know that it’s not as easy as it may seem.
I’m a polite person and I really don’t want to hurt anyone’s feelings by outright saying that I’m not interested. I’ve tried giving out a fake number but was once caught on that trick when I had my blackberry in my hand while we were still chatting and it failed to ring as he tried my number right in front of me.
Aaaaawwwkwaaaaaard.
I respect the fact that it took some courage to come up and ask a stranger for her number, I figure the most humane way is for him to call or text a couple times and when he gets no response to make up a million different reasons why I never returned the message.
Is this really that bad? If you have an idea of exactly how to politely duck out of giving someone your number, I’d love to hear it because I’m not really sure one exists.
Can I buy you a drink?
Thursday night I was out and about and a guy asked to buy me a drink. I figure this is probably the most common pick up situation out there so I will give you the play-by-play. Maybe you guys out there will gain insight or maybe you’ll be completely turned off by what goes through my mind in situations like this one – but I will be honest nonetheless. 
When I decided to close out my tab I left my group of friends and went up to the bar to do so. I squeezed in between two guys because if given the option when presented with a packed bar, I will find two guys and squeeze between them. This gives them the opportunity to strike up a conversation. Viola! The guy next to me says hi and asks me my name – works like a charm. We introduced ourselves and he asked me what I do. We had a simple exchange and then he asked to buy me a drink. Since I was planning on leaving (it’s was late on a week night) I turned him down and said no thank you but I’m heading out. He asked me who I was there with and also if I come there often (of course). I didn’t think it was a cliché thing to ask though as he said it pretty casually. I could tell he was interested in me and was going to try to keep me at the bar as long as he could with simple conversation. He was extremely pleasant and laid back, not aggressive or creepy so I was happy to chitchat. He asked me again if I was sure I didn’t want him to buy me a drink. At this point I asked myself, why wouldn’t I let him buy me a drink? I looked at him – really looked at him. He’s probably about 10 years older than me – not a problem. He’s a bit scruffy and extremely casual in his dress – not all too impressive but not a big deal. He has dark hair that’s kind of long and he’s slightly overweight – overall not my type. I declined the second offer. At this point I had learned that he was a paramedic so I reinforced my not having another drink with the fact that I was leaving and had to drive – this was true and I really had hit my drink limit. He said he hoped that he would see me back there in the near future. I said I’m sure I’ll run into him again as I liked the bar. I said goodbye and walked away with his gaze still on me. I liked that he stared after me. I also liked that I was the object of his affection for even just those few minutes it took to pay my tab. Mr. Paramedic will have to find someone else to play doctor with. Or, if I do return to that bar and he’s there, maybe persistence will win me over. I do like a fighter!
Your Dating Life: Out in the Open and Definable?
Filed under: Advice, Dating, Stories, Tips, Top Lists, Uncategorized
Single? Swinger? In a relationship? Engaged? How would you define your current relationship status online? If I was to answer that question in free form it would be: Seeing a guy who’s great in bed but not relationship material and dating another guy… we’ll see where that goes. I don’t see a status option that encompasses all of that so I pick “Single.”
Not only are we encouraged to state our status but we also allow our “friends” to post things to our profile publicly. It’s open season for cupid… and the rest of the world.
Part of the problem with this new scenario is interpretation. People don’t always see the humor, sarcasm, metaphors and context intended when speaking in 1s and 0s. So how do you read between the lines when interpreting what people post and how do you manage how others interpret what you post?
Here are a few recent scenarios I found myself in:
Three days before Valentines Day I get a message from someone who has been openly interested in me for years: “Would you consider flowers showing up at your house a romantic gesture?” My thoughts: OMG he’s sending me flowers, no he can’t do that! I can’t accept flowers from him! I wanted to type: DO NOT SEND ME FLOWERS. But after careful consideration I typed back, “Yes, that would be a romantic gesture.” Long story short, he was asking in regards to someone else (or so he says). I’m just glad I didn’t react and say exactly what I was feeling. It saved us both some minor embarrassment.
I recently went out on a date with a guy who I wasn’t physically attracted to in the least but he was nice and interesting to talk to so I went. After an awkward dinner and a fun show we hit up late night dessert. When we were waiting for dessert, he takes his camera out and asks the waiter to take our picture. He throws his arms around me and sports a huge smile. I didn’t look all that enthusiastic but I did smile. Two days after dashing into my house to avoid his goodnight kiss I see that picture, front and center on my profile online. Suddenly, I am interrogated by the masses… who’s that guy? Are you seeing that guy? Why didn’t you tell me you went out with someone? Not only is the picture public but the comments are, too! Thankfully I was able to delete the photo “tag.” In my book I tagged him a Big Loser.
As we all are, I have been reconnecting with old friends and in some cases, old lovers. Reminder, I’m listed as “single.” Most of these “new friends” are asking to meet up so we can reconnect. After setting up what I thought was a casual cocktail with a friend of an old lover (how complicated our lives have become!) I received a comment from him. I had posted some song lyrics, “And I’m just dreaming, Counting the ways to where you are” only intending for someone to recognize the song (how naive of me). “New friend” commented on this, “dreams will come true April 3rd, rest up!” My reaction: Uh oh, casual cocktails not so casual! And second thought: Shoot, current guy may see this – I’m innocent! After a deep breath and a sip of wine I decide to play this off as a joke until I can privately manage the situation. It’s all about damage control. I commented back, “You’re inviting George Clooney to drinks?” Let’s see how he likes them, cocktails!
My advice – keep it casual and light hearted online in your interpretation and in what you say. It’s not a place for those heart to hearts, let alone foreplay… leave that to phone calls, texting and one-on-one!! More on that later.

