Life & Times of a Hopeless Romantic

A 30 year old young professional shares his musings as he navigates the dating pool of the Windy City of Chicago.

Friday, April 28, 2006

Funky Friday..

So today happens to be one of those days where I find myself in a funk for no real significant reason -- I guess everyone goes through these lows sometimes; I just find it frustrating when I have no significant event to pin these feelings on. Even more strange is that earlier this week I was on such a high -- work was going extremely well, things with females were on the upswing and the weather was turning nice in Chi-town. Crazy how moods can alter so drastically in the course of a couple days...

One of the benefits I see of having a blog is that it provides a forum for allowing one to organize their thoughts and get things out of their head an onto paper..This is probably the main reason that I've chosen to start one of these thigns..

so let me start by commenting on the good that has happened this week --
1) Work continues to go well - While there are times I wish I was more busier, I keep telling myself that its better to be less busy than too busy; just as long as I continue to learn and grow along the way. My boss has paved the way for me to stay on my job full time which is good on a couple fronts -- it says that he thinks i've done a good job to date as well as provides an interesting exit option from consulting which i'd been thinking about. There are definitely some minor downsides towards pursuing such a position in that the my compensation trajectory would most certainly decrease, I'd be forced to remain in Chicago for a couple more years at least, and that my role is still somewhat undefined -- but I think the benefits outweigh the risk. Furthermore, I'm not locked in here for any specific amount of time so if I want to leave, I can do so. Now I just need to work out the negotiation side of things with both hotel firm and consulting firm...
2) Things with Aly were good ...we went out on tuesday night and had fun together..There are still some things that get me, but i'll elaborate more on those later..I then got a message from her on Wed saying that she thought I was a great guy. Always makes me feel good to get compliments from others (as i'm sure most people feel the same)

Now to try to put my finger on what's bugging me:
1) Women -- what's new, right? this always seems to get to me...There's not one major event that has brought me down -- just a combination of a number of 'smaller' things.

I never did hear back from Lauren -- and not that i'm necessarily 'crushed' b/c I didn't hear back from her in particular (although I did enjoy hanging out with her the couple times we got together and am bummed that the opportunity to get to know her better no longer exists), I think what bothers me more is the frustration involved with the whole dating process - Why can't dating be more normal? Why are people so guarded? so unclear with their emotions to others and themselves? Are there normal people still out there?

And why am I still single? While i'm no Brad Pitt in terms of looks, I'm an attractive guy who's a fantastic catch...It perplexes me to no end that I haven't found a partner where there is mutual attraction and interest in over 2 years now...(and no, i'm not trying to be self-rightous here..). I don't think its because i'm being overly picky or discerning...and it sure as hell isn't b/c I haven't put myself out there..

On top of the Lauren situation, there are still things with Aly that I find a bit strange...While there are clear signs that she enjoys my company and likes me, there are times where I find myself questioning what the heck is going on with her. One week she incessantly texting and calling me (to the point where its almost too much) and the next week I find it increasingly hard to get in touch with her [given we've only known each other for a few weeks now, but the swings in communication are quite strange]. I know part of this 'phenomenon' is in my head where I'm getting overly worried or thinking too much about what's going on like I have a tendancy to do -- but there's also an element of it where she is a bit out there; also, I think there are a number of things in her recent past which she is still dwelling on which I don't know about yet but which definitely affect the progression of our relationship -- she hasn't explicitly told me anything but its a sense I get (and have interpreted from other tidbits she's given me) and I'm usually pretty spot on about this stuff...we'll see where things go with this...

I'm acutally leaving for a 4 day vacation tomorrow and then one day back in town before taking off again for a 2 week business trip - so, it'll be good for us to have a bit of time apart to figure things out and like they say, time apart makes the heart grow fonder...but at the same time, its also kind of a bad time to leave as I feel like we're just getting to know each other...let's see what happens. We're also meeting for drinks this afternoon so we'll see what becomes of that encounter as well...

One other comment on girls -- I've been doing online dating on-and-off for the past year or so..its been an interesting an informative journey; both about the opposite sex and about myself -- one thing that i've found though is that there are a number of people that lack integrity -- maybe a strong word for such a situation, but i choose to use it nonetheless.

There have been a few instances where I have set up meetings/dates with women and they have completely flaked on the encounter -- I have no problem with people canceling dates; things come up, schedules get busy, people get cold feet -- but at least have the decency to call me so I don't alter my schedule for you and then have my night ruined in turn...I don't take it personally b/c these women don't know me and its not a personal affront -- but once again, its just an added frustration to the whole dating process.

2) Friends
This theme will probably come up often throughout the course of my blog -- its an issue I struggle with that is intertwined with self-esteem issues which I struggle with on occasion...Being connected is important to me, and a lack of connection can short circuit my happiness at times.
Nothing has really happened this week on the negative front but i've just been down slightly - maybe something to ponder a bit more

well -- that's all for now...I'll write more later as I wade through these emotions...

Off to lunch in a little bit with a partner from my old consulting firm to break the news that I'm thinking of leave and to discuss exit strategy -- it should be interesting to see his reaction...

Monday, April 24, 2006

Latest & Greatest

Just a quick post to update about weekend happenings...

Overall was a pretty good yet low key weekend -- actually met up with Aly on Friday night and went to a wine tasting at a Bain partner's house. We had a great time and it was especially neat given the fact that she's a wine buyer and has soo much knowledge about all the wines...It was also nice that she has such a warm/charming personality in that I don't have to babysit her when we go somewhere -- I tend to be a pretty social person who likes to 'work the crowd' so its nice to have a partner that is comfortable doing her own thing for a bit too...

On a side note, it was interesting that she actually cancelled a work event she had to go to so she could hang out with me on Friday -- such a contrast to the 'feedback' i'm getting from Lauren...While i'd say that Aly may be a little 'too much' right now, its so much nicer knowing that the person is interested, when they don't play games and are upfront -- just makes things flow so much more smoothly..

Saturday was a pretty chill day -- had brunch and then did some furniture shopping with John and Eileen..Fun times hanging out with both of them. Had totally planned to go out on Saturday night with Geoff and Brian and some friends they had in town but totally got caught up in doing things around my condo and fell asleep early (so lame!). It kind of made me mad at myself as I was psyched to not only see those guys but also to have a big night out...

Sunday was another do-nothing day -- I mean I got some stuff done around the house but never really made it outside until my soccer game later that evening...On one hand, it was great that I got alot of little errands/chores done but at the same time, I felt like i kind of wasted my day...I need to do a better job of getting 'up and at 'em', especially now that the weather is nice...

Alrighty -- that's all she wrote for now..I'm getting pretty fired up about my upcoming golf trip to Phoenix this weekend with Brent -- I haven't spent some QT with him in a while so i'm psyched to get 3 or 4 days to just hang out and catch up...also, it'll be nice to have a little vaca as well...

It'll also be interesting to see how the Lauren & Aly sagas play out this week.. Lauren supposedly got back from all of her travels last night so we'll see if I hear from her in the next day or two. Aly and I, on the other hand, have plans for Tuesday so it should be fun to see where that takes me as well...Oh, not to mention that I have another first date tonight with a girl Stephanie who my friend Lisa set me up with -- got all that?!? at least it keeps life interesting...

more later this week...

Thursday, April 20, 2006

Back for Round 2 (pt.3)

THE LAST EPISODE (finally..)

to continue where we left off -- when we last left our hero (me), he had just received a call from Lauren on Friday afternoon to give her a ring back -- unfortunately my phone had died and I didn't get the message until Saturday...

Saturday afternoon I had tickets to the Cubs game and ending up bringing a different girl who I recently went out with (Aly). Had a fun time at the game; opening weekend in the bleachers, good company, and Old Style Light -- how can one go wrong? Met a couple friends for a beer or two after the game and dropped Aly off around 5pm...Decided to give Lauren a ring back in my half drunken state and once again (what's new) got her cell phone....left a message...

No call back on Sat, no call back on Sun - not that this was a huge deal, but I guess I am under the impression (someone call me out on this if i'm totally out of line here..) that if a girl likes someone, she'll make it her business to call him back..not sure why she so delayed in her response -- once again, this middle of the road, wishy washy reaction which I can't understand

Anyways, i digress --- She calls me back on Monday evening, from the airport no less -- finally we happen to connect -- she's actually off to Las Vegas to meet her parents for her birthday (see, I told you she's a cool chick..). We talk for about 20-30 minutes and I come to find out that she's actually gone for the next two weeks (Vegas, a couple weekends at home and a business trip to Tokyo) -- she even apologizes for being so unavailable, which to be honest, she really didn't need to do...Given my hectic life at times, I completely understand busy schedules...

It turns out she's coming back on Thursday afternoon from Vegas and my folks are coming in from Texas to visit for the weekend late that evening so there's actually a window in there where we can potentially get together..So I casually throw out the suggestion that maybe we get together for a drink on Thursday night..Caveating the offer with the fact that I know she'll probably be tired from a couple days in Vegas and that she'll want to pack for her next trip so I understand it it doesn't work out, but we should talk nonetheless...

Thursday rolls around and I get a text from her around 7pm..."I think its going to be a couch and gym night for me -- I've been up since 4am and i'm exhausted. Talk soon."

Weak sauce. I totally understand if you're tired and don't want to hang out; but come on...give a brotha' a break -- at least have the courtesy to call, especially if you're interested....Bummed, I begin to get the sense that she's blowing me off...

I've almost completely written her off 30 minutes later, when all of a sudden, another text message from her comes through .."btw, Happy Passover".

once again, Brett = CONFUSED.

I really have no clue at this point where this girl's head is at -- if she wasn't interested, as I had recently decided, then why the heck would she send me a 2nd text message...huh?

Anyways, I decide to give her a call to see what's up, hear about her trip and see if we can get some time in her calender to hang out when she gets back...I dial her number and sure enough,,,NO ANSWER...what?!!? she just sent me a text no more than 15 minutes ago -- is she screening my calls? now i'm even more confused...once again, i'm resigned to leaving a message...

of course she calls me back as our normal mode of operation has become, but strategically calls back at 8pm when I assume she knows that i'll be out to dinner with my folks and can't pick up (maybe i'm thinking about this too much -- but she did mention in her message that guessed I was out with my parents so I wasn't picking up...double HMMM..).

Hoping to end the game of phone tag, I call her back Sunday evening, hoping to talk to her a bit before she takes off for Tokyo -- of course, no answer and no call back that night...

SOOO...that's where things stand now...She's off in Tokyo and coming back to the U.S. tomorrow to hit an engagement party in Philly -- will probably be back in Chicago on Monday...

I guess the ball's in her court right now, but I totally hate that feeling, the feeling of being helpless and not being able to proactively address a situation -- i guess that's the strong Type A in me...

All in all, I have no clue what to think - my gut tells me that she's not interested as many signs point that way...but its definitely slightly perplexed b/c she continues to call me and our conversations are still fun...maybe i'm wrong here...

Would love some outside commentary if anyone has any opinions...

I'll continue this story if and when things progress...

Word.

Duke lacrosse Conundrum

Not sure how many people have been following the scandal which has occurred at Duke between the lacrosse team and the "dancers" they hired, but its been garnering alot of national media attention of late -- for those of you in the dark, the strippers claim that three of the lacrosse players forcibly choked her and raped her after they had hired her to dance at their house...The lacrosse teams completely denies this took place and initial DNA tests show that none of the players DNA were found on the girl's body...

It also seems as if its led to a number of other subplots, most notable exposing an underlying issue of racial tension within the town...

I guess I'm a more interested observer than most given my ties to the university (I went to grad school there..); However, I came across an article on ESPN (posted below) yesterday which shocked and kind of sickened me..

http://sports.espn.go.com/espn/news/story?id=2413794

Turns out that sales of Duke Lacrosse gear have tripled since the incident occurred -- what gives? I can't quite understand why this would happen...Obviously their fan base didn't triple overnight -- also, even though nothing has been proven yet, I can't imagine that people would want to flaunt their support or approval of the players..Can someone please explain this phenomenon to me?

Tuesday, April 18, 2006

Back for Round 2 (pt.2)

CONTINUED FROM BEFORE...

now what you've all been waiting for, the continuation of the Lauren saga. When we left off last, I was 'banging my head against the wall', trying to figure out what the end of the date 'meant'. For the sake of my sanity, I finally decided to just let it rest and see what would happen when I called her next. I figured that I couldn't have completely whiffed on my interpretation and that she had a good time with me -- maybe she just didn't want to kiss me on the first date?!?

Anyways, I give her a buzz two days later on Sunday early evening around 5pm -- of course, no answer on her end...I leave a message and begin to anxiously await her phone call..6pm, 7pm, 8pm...still no return call...9pm - phone still silent {COMMENT: I realize in retrospect that this behavior is rather freaky -- just b/c she doesn't call me back right away, means little to nothing...However, I'm just including the way it actually happened to show a true representation of my anxiety at the time -- I guess it was just a real indicator that I did like this girl and wanted her to call me back...).

I go to bed that night and lay awake questioning, trying to figure out what the end of Friday's date really meant, replaying events in my head...I doze off and awake Monday morning after a restless evening...Go to work and surprisingly don't think much about the girl...Day ends and I'm actually scheduled to go on different first date that nite -- however, I can't get my mind off Lauren (at this point, I'm really acting like a freak..). Go meet this other girl (Lindsay) for drinks -- actually have fun, joke a bit, have a few drinks -- but still no phone call...At this point, i've written Lauren off -- obviously I misinterpreted her on our date...Then just as my time with Lindsay was ending, I get a text from Lauren...

"I'm still out with my friends at so and so event -- sorry its getting late -- can i just call you tomorrow? hope you had a good birthday" [It was my birthday the previous weekend)

Saved.

although once again I don't know what to think -- on one hand, she took the time to text me while she was out with her friends. (INTERESTED). On the other hand, she could have called me on her long drive home from the suburbs which she has every day (NOT INTERESTED). is she just playing games with me?

I decide to stop being stupid and just let it be. I text her back "Sure, just call me tomorrow" and let it be. Sure enough, she does call the next day - I miss her phone call. [You'll soon see a pattern here..] I call her back tomorrow - no answer - leave a message "i'm heading to the gym for a bit but will be around and up late tonight, give me a call"...Sure enough, I don't hear back from her that night...

Thursday rolls around and I get a call from her around 6pm as she's leaving work (and I'm heading out the door for the Coldplay concert with friends). We chat for about 15-20 minutes, have a funny lighthearted conversation (like we usually engage in -- i often find myself laughing when talking to her..) finally I have to run off to meet my friends for the show...

"So, I'm out of town this weekend but any interest in getting together early next week?" I pose to her...Fully expecting her to say yes...

"Well, actually next week doesn't look so good for me ...I have a work event early in the week, then I have birthday events and stuff later in the week...why don't we just talk next week?" comes the reponse.

Shock. Despair. Anger?. Surprise -- what all does this mean? I always assumed that if the girl returned your phone call (especially 2 phone calls) that she was interested in going out again...This threw me for a loop..So I decided to go with the only weapon I knew in this situation -- honesty...

"Well let me be honest here ...Just want to make sure that you do want to go out again sometime...". I say...

That must of thrown here for a bit of a loop - but she recovered well and said that she in fact, would like to hang out again..

Okay. sigh of relief on my end...

"Well, let me try one more thing then -- i have an extra ticket to the Cubs vs. Cardinals game this weekend (in the bleachers no less)...do you want to join me?"

"I would love to - but I have a friend in town...sorry ...i'm just full of bad answers, aren't I?".

SHOT DOWN AGAIN. pain. agony. (ok, i'm exaggerating here - but you get the point)

Resigned to go home with my tail between my legs, I attempt to pick up the remaining dignity I have and simply let her know that I'll call her in a week or so then when things are back to normal for both of us...

Fast forward a week --

Resigned not to give up, I give her a call a week later...I'm back from a great weekend ski trip in Vail, fresh and revived, ready for another 'attack' ;). Calling on Wed after work, i dial her number on my cell phone..

ring.ring.ring -- i see the phone connect on the other end. "Lauren" i say..no answer. "Lauren, you there?". no answer again. I hang up

Assuming that there's something screwed up with her cell phone VM, I call again to hopefully leave a message on the answering machine. Once again her phone picks up after two rings, but nothing happens on the other end. just my luck. Then 3 minutes later, I see an incoming call from Lauren. Interesting. I pick up but once again there's no one on the other end. Strange?!?

Since i'm on my way out again that night, I decide to try one last time before i leave for the night so I can just leave her a message on her cell phone. dial her number once more -- finally I reach her VM and leave a message (and apologize for calling more than once, explaining the VM problems I was having).

2 hours later, I get a text back from her explaining the whole mess -- turns out the speaker on her cell phone broke and when she picked up earlier, she could hear me but I couldn't hear her. She mentioned she'd try to call me in the next day or two when her phone was fixed.

Cut to FRIDAY -- i'd been out on a couple nights of partying (seems to have been my M.O. lately) and let my cell phone battery run out -- what do you know, but Lauren happens to call on Friday afternoon when I have no phone access...even leaves her work phone number for me to call as well if I get the message soon...

HMMM...does this mean that now she's interested...?!?

Brett = Confused.

STAY TUNED FOR PART 3...

Back for Round 2

So initial impressions -- I like this blog thing...A great forum to get stuff off your chest. At the same time, others who read your thoughts can provide an independent opinion (...or shake you from your delusional state ;)..

Back to the issue at hand -- females...The latest vixen in my life who has thrown me for a loop, is a girl by the name of Lauren...this brief story should provide some insight into the way my mind works...

I was introduced to Lauren a few weeks ago by a friend of mine..His girlfriend was a good friend of Lauren's from bschool and decided that we should meet. I'm pretty laid back about this stuff and like to think that I could talk to a wall if necessary, so was totally up for meeting this girl -- after going through many iterations of trying to find a day that worked for us all, we finally settled on a night where Lauren could meet up for drinks ..

We met at a local bar called Guthrie's -- kind of a dive, but a fun dive with some real neighborhood atmosphere..I went early to meet up with my friend and his girlfriend...Lauren joined us later along with another couple...

Now I wouldn't describe Lauren as a knockout necessarily -- she's a cute girl (with a nice body) but you wouldn't necessarily pick her out of a crowd. I've dated many women more attractive than her before -- but something about her drew me in...we share alot in common in terms of our background and both seem like the type of people who are always out and about; do'ers if you will. Besides, I decided at the end of my last relationship that looks were alot less important to me -- some physical attraction is important of course, but it's not my #1 criteria...i've dated models before who were just painful to hang out with...

anyways, i digress - so the 6 of us were hanging out at this bar for a good 4 hours, drinking, having a good time, and playing board games (that's the schtick of this bar). The night ends and we shuffle outside to grab a cab - I suggest to Lauren that the two of us share a cab since we're headed in the same direction. She seems a little taken aback by the suggestion but agrees to the proposal...We flag a cab and jump in -- to her place first since she lives closer to the bar.

Our (good) conversation continues...Of course, like the idiot I am, I wait until the last possible minute to ask her for her phone number so its the most uncomfortable, preplanned moment possible..I fumble over my words a bit as I always think asking for a girl's number seems so obvious and so gay, but i get my message across and she gives me her digits (she had to know I was going to ask for them, right?)

Following 'the rules', I wait two days to give her a call -- [actually, i probably should have waited longer if I was following the rules but i'm so over that by now]. At some point during the next week, we finally get in touch and make plans for that upcoming Friday night -- she actually has a happy hour event earlier in the night but agrees to meet me afterwards for dinner.

I make reservations for dinner at this great little Italian restaurant, one of my Chicago favorites - she shows up after her event, looking pretty good. Dinner goes great -- I really enjoy our conversation and find myself liking this girl more. Once again, don't find her amazingly attractive physically, but am drawn in by her personality -- she's a very fun girl. In a weird way, I feel as if she's almost intimidated by me -- i'm not sure why that would be; perhaps because i'm a pretty energetic, effusive person -- but who knows. Anyways, dinner goes well; we basically shut the restaurant down ...head outside and decide to head to another bar for further drinks (one would think that the date is going well at this point, right?)

So off to the next bar we go - I know this cool, romantic wine bar near by and we head there for more cocktails...find a couple comfy seats by the faux fireplace at the bar and order a bottle of wine. Once again, great conversation ensues...I truly don't realize how much time is passing and all of sudden its 2am and they're kicking us out. Wow, i've never really had one of those experiences on a first date where you really don't realize how much time is passing...good sign I think...

We hop in a cab and head to her house to drop her off -- Cab pulls up to her door and like the southern gentleman I am, I get out of the cab to walk her to the door ;)...We get to her front doorstep and its somewhat of a uncomfortable ending...I always feel rushed (and like i'm being scrutinized) when a cab is waiting for me -- Anyways, i walk her to the door and let her know that I had tons of fun tonight...I then lean in for the brief goodnight kiss but somehow end up with the corner of her mouth/cheek...

What just happened there? Did i miss? (wow, that would be tragic) or did she turn her cheek? (which would totally surprise me). Confused, we talk for a few more seconds and I try again -- once again, I end up with a half-ass kiss on the corner of the mouth/cheek!

At this point, I'm throughly confused-- In general, I'd like to think that I'm very good at reading and understanding people. On top of that, as I mentioned before, I've dated many girls in the past 18 months and have gotten pretty good at reading whether or not the girls I am out with are having a good time...I thought for sure that I was getting a positive vibe from this girl -- Could I really have been so wrong?

Throughly confused, I head back to the cab to head home, wondering what the whole 'drop-off episode' just meant...what the f*Ck? As usual when those situations arise, my brain starts to whirr, attempting to make sense out of the pieces of the puzzle...

TO BE CONTINUED...

Monday, April 17, 2006

Popping my blog cherry...

I've always wanted to write a journal -- I get motivated for a couple days and then lose sight of my goal...my lofty ambitions fall by the wayside and my journal goes untouched after 8-10 'brilliant' journal entries.

So this is where I pin my hopes and dreams of sustaining a journal through the wonders of modern technology.

A bit about me -- I'm a male, currently residing in the Windy City of Chicago...I've recently hit the life milestone of the Dirty Thirty club (my 30th birthday) which hit me much harder than I thought it would. The concept of marriage and starting a family is one of the most important goals I aspire to in my life and I always thought i'd be long committed by now. Unfortunately, life doesn't always work out the way you expect it to and I found that I had many kinks to iron out before I was truly ready to settle down.

After finding myself on the back end of a serious relationship in Jan 2004, I entered into a long (and painful) period of self introspection. Through this period of growth, I finally came to realize what I wanted out of a relationship and what was most important to me - I matured enough to be ABLE TO BE happy and satisfied in a committed relationship. You see, one of my big problems before was that I was guilty of the 'grass is always greener' game when I had a girlfriend...it always seemed to be a better option to be single when I was dating someone (and vice versa when I was single). This confliction lead to a wandering eye and a couple of indiscretions in my past (which i'm not proud of).

Anyways, I digress -- As I was saying, I now find myself at the ripe old age of 30 and ready to enter into a serious relationship. Unfortunately, I still have yet to find that girl to form that other half of the bond (a bit of a problem, don't you think? ;)...In my 18 months or so that i've been in Chicago, I estimate that i've dated over 50 different girls -- kind of crazy right?

Its not that I keep striking out -- many of the women wanted to continue dating; in some instances I either lost interest or never felt a spark, other times I think my head just wasn't in it for some reason (who knows?), and there were a few that I really liked who wanted nothing to do with me :) Overall, I think that i'm a pretty good catch -- a relatively attractive guy (i'd give myself a 7.5 out of 10), schooled in the Ivy league, successful, athletic (former college athlete) and i'd like to think an all-around nice guy...

This is where my blog comes into play -- the main topic of the journal will be an 'insider's' view to my (hopeless) love life and my internal conflict as I attempt to make my way through the dating pool..Trying to figure out what i'm doing wrong and what i'm doing right

Any advice or comments others wish to make are welcomed -- i love a good debate...many happy returns.

-BL