Since I have a crazy and fluid job, which is difficult for many people to understand, and a bank account that is in desperate need of a Government bailout, (if anyone has Ben Bernanke’s direct line please email it to me) one would rightly assume that the chances of me going out on a date with an attractive, successful lawyer were slim; however, I proved all the skeptics and naysayers wrong when I recently went out on a first date with such a woman.

We texted during the day and ended up choosing an Urban BBQ restaurant for dinner that was near her apartment in River North, which is a very trendy area just north of the Loop. I left work around 7:15pm and picked her up promptly at 7:45 so we could make our 8:00pm reservation. The restaurant was just under a mile from her apartment so I quickly navigated through the city before beginning the (often times) laborious task of searching for a parking spot. Since the weather was cold and rainy I was praying we would get lucky and find a spot within a block or two of the restaurant, and after driving around for just a few minutes we fortunately did.

Now, for those of you who are unfamiliar with how parking throughout most areas of Chicago works I will explain our system so that we are all on the same page. Essentially, a few years ago, the city privatized all street parking, and the company who bought the right to charge for parking tore down all the old-fashioned parking meters and replaced them with pay-boxes. Tall signs with green writing and arrows indicate where pay-box parking is allowed, and if you find a spot within one of those designated areas all you have to do is simply find the closest box to where you parked and, using coins or a credit card, purchase up to two hours worth of parking time.

After parking in a coveted pay-box spot that we had found about two blocks from the restaurant I bought my ticket and placed it on the curbside area of my car’s dashboard. With that exercise completed, we briskly walked through the elements to the restaurant and had a lovely dinner. The food was excellent, the conversation was interesting and she seemed to be having a very nice time. Even though throughout much of the dinner I felt slightly uncomfortable since she was obviously an independent, successful women and I’m, well, me – a financially limited, work obsessed– albeit dashingly handsome–College Basketball Coach, I tried to remain confident and be myself.

Anyway, so we have a nice time at dinner, and after taking care of the check we leave the restaurant and head back to my car so I can drive her home. During the short walk I debated in my head how I wanted to play things, and tried to figure out what was my best course of action in asking for a second date. Yet, I was abruptly forced out of my daydream and back into reality when we turned a corner and, wouldn’t you know it, my car wasn’t there. In a moment straight out of the classic stoner comedy, “Dude Where’s My Car?” she literally turned to me and asked, “Matt where’s your car?”

For whatever reason the first thought that came to mind was that we had parked further down the block, but it didn’t take much of a “Spidey Sense” to realize that we were standing in the spot where my car should have been. The next thought that jumped into my head was that my car had been stolen but the fact that I own a 2004 Mitsubishi Lancer with two missing hubcaps and several cosmetic scrapes on the sides was probably a pretty good indicator that it hadn’t been jacked. Furthermore, while I was contemplating what type of individual would be desperate enough to steal my car, my date noticed a sign at the end of the block, which we had missed when we originally parked, indicating that while I was in a valid pay-box spot, and was not over the time that I had paid for, I was unfortunately in a spot that was designated for taxi cab parking only between the hours of 5pm and 2am.

Whoops.

As it sunk in that my car had been towed, while on a first date, no less, I remained remarkably composed and calmly pulled out my phone in order to find where I could retrieve my displaced automobile. Even though she felt terrible, and was very sweet and understanding about the whole ordeal, I figured the best thing to do was put her in a cab home, bail out my jailed car and try to forget about how, at the last second, I embarrassingly blew my chance with a successful, attractive lawyer.

I think that the place someone picks or suggests for a first date can, in some cases, tell something about them. Perhaps a female would have better perspective than Isince, as the asker-outer, I am normally the one who ends up suggesting the activity or meeting spot; I would still like to offer up my two-cents on the topic, anyway.

As someone who puts a great deal of consideration into where to take a woman on a date, I am always trying to suggest places that will we be different or off the beaten path. Therefore, if a woman was to suggest to me that we go to a generic place where everyone and their brother knows about, I might be slightly put off by the lack of imagination in their suggestion.

You see, for me, a first date is a time to test people a little bit – see if they are really willing to try new places and venture away from their neighborhoods to explore all that the city (of Chicago) has to offer. I honestly think that it’s fun to take people out of their comfort zones a little bit by taking someone to place that they admittedly haven’t been or to an area they don’t frequent very often.

Tonight I am going out on a date with a woman, at her suggestion, to a restaurant whose cuisine I haven’t ever tried, in an area that I’m not very familiar with, and to be quite honest am very excited about our impending adventure. This isn’t to say that if a woman suggested a generic place for a first date that I would write her off, because there is something to be said for that approach. HOwever, the fact that this woman would suggest this particular restaurant for our first date indicates something cool about her to me that I am looking for a in a woman.

Recently I’ve spoken with several women whose profiles identified them as being in Chicago when in actuality they were really moving to Chicago soon and had joined 100hookup in order to help ease the transition. My initial reaction was that I felt slightly misled, especially by the woman who told me she wasn’t moving to Chicago for another month. However, after getting the chance to think about it, I’ve come to realize that this really is a great strategy.

Even though I’ve always view 100hookup through a narrow lens, where I only saw it as being a “dating” site, when I really think about it thiswebsite is much more than that. The site is a way for people to connect, meet people they wouldn’t normally meet and provides another way for people to form meaningful relationships. The most important aspect of the site is not that it matches people up who will eventually fall in love and get married, but rather that it lets you use the site in whatever way best suits you and what you are looking for.

That’s why the idea of joining 100hookup before moving to new city is such a great idea because while some people on the site are looking for love, others are simply looking to meet people and connect, even if it’s just as friends. Perhaps I wasn’t interested in being an activity partner or friend to someone who had just moved to Chicago, but I’m sure there’s someone else on the site who is, and that’s the beauty of 100hookup and the community it fosters.

Recently I’ve noticed that as the weather has steadily improved in Chicago, more people are logging onto 100hookup. Maybe it’s just a coincidence but personally I think that when people look out their windows and see snow and ice covering the streets they are much less likely to have the desire to leave their homes in order to go out on a date. Braving the elements to go out on a first date with someone you’ve never met can be a bit of a stretch at times; however, as the seasons change, I believe so do the mindsets of many people.

Even if you are unsure about going out with someone, agreeing to go for coffee or on a walk through a neighborhood is something you might do anyway if the weather was nice, and therefore are more likely to give the date a chance. Also, in my opinion, the spring is an ideal time to try to meet someone since then you’ll have a special person to do all of those fun summer activities with. Right now, as we start to see more of the sun and the days get longer, it’s the perfect time to break free from your winter dating slumber and get back out there. The built in excuse of it being too cold and gross outside is gone, and outdoor activities are back in play when planning dates. So go out and have fun because spring has sprung and so to can your social life!

Since moving back to Chicago permanently in August I have made it my goal to be more social and, in turn, bring some much-needed balance to my life. Not only have I tried to see friends and go out more frequently, but I have also attempted to meet women and go out on dates. Most of the women I’ve gone out with I have met on 100hookup since my job takes up much of my time and energy, especially during the season.

While online dating has overall been a very good experience for me, and has led to two relationships (for lack of a better word) that have lasted longer than 2 months, most of my interactions with women I meet online result in only an exchange of emails or a single date. In some of these situations I have been the one who ended things because I lost interest or didn’t feel a spark when we went out, but in other cases it has been them who has moved on.

Regardless, the simple fact that I have continued to talk to women and go out on dates intermittently is something that I know is good for me and that I need to continue. Although recently I’ve gone out on several first dates that I was excited about, however none of them resulted in a second date. In a few cases I decided not to ask them out again, but in the others they have been the ones who lacked interest. In either case since the season started back in mid-November I haven’t gone out on any dates where both of us had a good time, felt a spark and wanted to go out again.

In spite of my lack of dating success over the past few months I can honestly say that I haven’t become frustrated or disenchanted with the process because I know that dating can be very unpredictable. Additionally, part of my life philosophy is that things tend to happen when we least expect them to, and I know that unless I continue to go out on dates it is highly unlikely that a woman, and relationship, will just magically appear.

I live in Chicago and for those of you who have never visited the Windy City during the winter it is freaking cold! I won’t get into the specifics but we have this crazy thing called the “Wind Chill Factor” that says how cold it feels outside when you take in account the wind, which is always at least 5-10 degrees colder than the actual outside temperature. Add in the snow, which inevitably turns to gross dirty slush, and you have a situation where most people don’t want to leave the warmth and comfort of their house between December and March.

If you live in a part of the country where this is the unfortunate situation during the winter months then, like me, you might be experiencing a lack of motivation when it comes to meeting people and going out on dates. During the summer so much is going on, which makes it much easier to remain in a constant social mindset; however, during the winter, our tendency is to go into Hibernation Mode which is often times a difficult mindset to reverse. Your friends that are couples might opt for a quiet night at home instead of going to the bars, and people who don’t live near you may decide to go out in their neighborhood because of the hassle of travel. What this is all means is that there are less imminent opportunities to meet people and be social during the winter.

Additionally, when it comes to online dating, it seems to me that less people are interested in talking since that social edge they road just a few months ago has been covered by a sheet of snow and ice. However, I would submit to you that the winter is the best time to go out on dates since the extra commitment it takes to live up to plans usually signifies that the other person is actually interested in you and not just going out to go out. So don’t let yourself take the easy way out and let the nasty weather outside be your excuse for not remaining active and trying to meet people. Just remember: Sitting in front of a fire with someone else is a heck of a lot better, and warmer, then sitting in front of one alone.

I know that it’s not the preferred method of communication by everyone but, regardless, I love texting. First off, it is casual and informal which syncs up well with what many people enjoy about online dating. Second of all, people are busy and they don’t always have time to respond to lengthy emails, or carry on long phone conversations where you can really get to know a lot about someone. However, perhaps the reason why I enjoy texting the most is that it’s fun.

Recently I began talking via email with a woman that I met on 100hookup, However, due to the travel schedule imposed by my job, we weren’t able to plan a date during what I considered to be the prime window. Fearing that I would miss my chance I asked for a date anyway just so that I could get her number and see if I could figure out a way in the interim to delay our first date without losing our momentum. That was where texting came in to play and was key to keeping everything going.

Around the time I was set to go on a road trip, I texted her in an attempt to begin a conversation and keep things progressing. She responded and seemed receptive to a texting conversation. As a result we’ve been texting back and forth for the past few days that I’ve been out of town, and through short messages we have been able to carry on a conversation where I think we’ve learned a lot about each other.

Instead of putting what we were doing or what some of our interests were in an email we’ve talked about them via text. In addition to our casual correspondence we made plans for a date when I got back. However, due to weather conditions in Chicago, our flight back was cancelled and I had to postpone our date. Perhaps had we been emailing and not texting she would have understood this situation; however, through our text messages she was fully aware of my situation.

In fact, she even suggested, after I told her that my flight was cancelled and our first date would have to be pushed back another week, that we continue texting and talking, which made me feel really good. Ultimately, I know that not everyone is going to be cool with this form of consistent communication, but right now it’s really the best way for me considering my schedule. In the end I appreciated her understanding and in spite of how well we’ve corresponded via text message I do plan on calling her from the airport later tonight so that we can finally take the next step in our relationship and chat over the phone.

As a blogger for 100hookup I certainly have no problems expressing my opinions on the virtues of online dating. During the time that I’ve been on the site I have benefitted greatly from how it provides a forum to meet people and get to know each other, as well as making dating easier for people who are very busy or don’t thrive in the bar scene. In addition to those reasons, and others I’ve talked about in past blogs, I can honestly say that I’ve had a very good experience with online dating. Even though I was already sold on the online dating experience, recently I discovered yet another reason why it is such a great option for me.

Last week our team embarked on a week and a half long road trip (for those of you who don’t know, I’m a college basketball coach) to play games in Utah, California and Texas. In past seasons I would have completely disregarded my social life and been forced to focus solely on my job since it’s difficult to meet women on the road. However, since I can meet women online no matter where I am, on this current road trip I have continued to be active online emailing and chatting with women I am interested in.

Furthermore I have continued to try to make plans for when we get back from our trip so, in actuality, because of online dating, I have continued to be able to try to meet women in spite on my being across the country for work. Just like when I talk to women while sitting on my couch at home in Chicago there’s no guarantee that I’ll go out with anyone I talk with while I’m on the road, but at least I am continuing to be social and trying to date. As someone who is constantly trying to achieve a balance between their personal and professional life, I am grateful for online dating since it has once again provided with me the opportunity to continue that pursuit where in the past I would have conceded all my focus and energy toward my job.

Last week I went out on a first date with a woman I had met on 100hookup about a week and a half prior. She had originally instant messaged me and the conversation had gone so well that we began emailing the day after. Our email correspondence was so interesting and engaging that it led to us making a date to meet for dinner at 7:30 last Wednesday. I was coming straight from work and was going to have to drive through downtown Chicago in order to get to the restaurant, so how long it would take me to get there depended heavily on whether there was traffic in the loop.

Despite worrying that afternoon that I wasn’t going to get out of work in time to make dinner, I ended up leaving only a little after 6:30. While walking through the parking lot to my car, I used the GoogleMaps™ app on my iPhone^® to confirm directions and predict my approximate travel time: 35 minutes, so it said.

Now with the knowledge that I would arrive in plenty of time, I drove confidently to my date with the tunes cranked up and little on my mind. As I flew through the city and reached my exit quickly, I realized that all I needed to do once I got off the highway was go about half a mile west before I would be at the restaurant. However, subsequent to this realization, it also dawned on me that I would be arriving twenty minutes early.

Even though it’s obvious that I would rather be twenty minutes early than even a few minutes late (call me old-fashioned but a woman that I’ve asked out on a date shouldn’t be the first one to arrive and have to wait for me), I was slightly unsure how I was going to pass the time. Furthermore, standing outside the restaurant, which was located on a busy street, became more and more awkward the longer I loitered. Unfortunately, as the result of my discomfort, after about 10 minutes of waiting I started to get inside my own head.

I began to get nervous thinking about how much she would look like her pictures, if we would have anything to talk about and whether the date would go well, in general. When she finally arrived, just about exactly on time, I definitely wasn’t feeling as good as I had when I was flying through the city, blasting music and singing at the top of my lungs. As a result, it definitely took me longer to settle into the natural flow of the date, though I must say that I think I rallied well and we both ended up having a nice time.

Even though you only get one chance to make a first impression, which obviously puts extra emphasis on it being a good one, that isn’t always going to happen. Ultimately, you just have to try to keep your confidence up, (in spite of the fact that you haven’t initially made the impression that you had hoped to), and do the best you can to be yourself and feel comfortable during the rest of the date. In life, how we look when we finish is often far more important than what we looked like when we started.

*iPhone is a registered trademark of Apple Inc.

I feel fortunate that I get contacted by quality men on this site.  Full stop.  Unfortunately for me, at least half the time these men don’t live in the most geographically easy places, let’s say Chicago.  Overlooking the fact, I am a “Miami Beach gal” at heart and can’t ever imagine how I would survive a Chicago winter.  I struggle with how you get to know someone, really know someone, on line and via phone.  Also, isn’t physical and in-person chemistry at least 50% (if not more) of the equation?  I often get pushback from these pursuits when I graciously decline. A lot of these folks don’t seem to struggle like I do and are more open-minded that their beshert may be across the country despite the energy this cyber geographically undesirable courtship may entail.

Of course, if I met a special someone that happened to live in another city, I could be persuaded that the relationship is worth the go.  But as for cyber cross-country courting, honestly the thought alone sounds exhausting.  But perhaps I need to be more open.  Perhaps I’m cutting off the nose to spite… and my partner may live in dare I say Alaska or Minnesota.  Aha, but then again, I do live in NYC where singles seem to be as abundant as bagels. Hmmm something to ponder…