Author Archive

Let’s Talk About “Us” Baby

by RollingStone9862 under Relationships

Generally speaking I think that after you go out with someone on three dates it is fair to say that you are dating them. This doesn’t mean you are exclusive because certainly it is within your rights to be dating multiple people at the same time, but regardless I think that three dates = dating. Unfortunately after my “three dates = dating” rule I really have no other rules for how to categorize the steps the steps within a relationship, which is why one of the elements of dating that I struggle with is getting a good how the other person views me and our relationship.

It is difficult before you have a discussion about where you each stand in the other’s eyes to know exactly what the expectations of a given romantic situation are. Certainly this is a subject that needs to be handled with care so that no one’s feelings get trampled in the process, but what happens when one of the people involved is resistant to the discussion? Does their opposition to talking about the status of the relationship mean something in itself?

Within weeks of when I first began experimenting with online dating about a year ago I met someone and we dated for several months before deciding to break it off. We got along really well, and had tons of fun together; however whenever I would bring up the status of our relationship she never seemed to want to talk about it. After some probing she admitted that she simply wanted to keep going with the flow, and not define what we had with labels, but I always had difficulty accepting this explanation.

Certainly I don’t blame her for the way she felt, and to an extent I understand where she was coming from; however I believe that after a certain period of time you come to the point where you want to hear from the other person exactly where you stand and where they think the relationship is heading. Unfortunately we weren’t on the same page in this regard, which is perhaps one of the main elements which lead to our demise, but that’s just sometimes how things turn out in relationships. In the end, even though we broke up, I did learn something from this situation which was that I am someone who feels much better being in a relationship when I know exactly where I stand.

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I Never Liked Tennis

by RollingStone9862 under Relationships

I always thought there was supposed to be a point in a relationship when you both just “know” that it’s time to take the next step and be exclusively dating. Perhaps it’s when things, such as talking on the phone, going out or sleeping over become natural and assumed, instead of meticulously planned out, but I’m sure the signs are slightly different for everyone.

However, what do you do when you’ve seemingly reached that point with someone but are unsure if they’ve reached thesame level of comfort and commitment with you? Do you talk to them about it and risk freaking them out with the thought that you are trying to make things more serious than they are ready for? Or do you hold off for a little while in hopes that the other person catches up to you so you are both comfortably on the same page? Well, these are all good questions; but in my present situation I am unfortunately lacking good answers to any of them.

Honestly, I wish I was the one on the other side of this situation, but sometimes in life we just have to deal with the fact that the ball is going to remain forcibly stuck in our court pending us making a firm decision. In my case I’m not entirely sure what that decision will end up being; I do know that I need to make one soon because I know deep down that constantly thinking about the unknowns related to my current situation is going to be far worse than the results of the conversation where I finally decide to bring things up.


My Life; My Choices

by RollingStone9862 under Relationships,Single Life

I think that most people who know me would say that my lifestyle, mostly because of my job, is pretty unpredictable. Many of my friends from both college and high school have lives that look much different than mine, and on the surface appear to have things much more together than I do. Since graduating from college I have worked for four different schools in  five years (all as a college basketball coach), and have lived in New Mexico (two years), New Hampshire (one year) and Florida (one year) before taking a job in Chicago last August. Most people I know, while they may not still be at the same “place” they were right after college, are at least in the same city and appear to be on a stable and progressive career path. I, on the other hand, work in an extremely fluid profession with a turnover that appears to be accelerating with each passing season, meaning there are no guarantees year to year that I will be in the same city or even have a job, period.

I believe that there is a general list of assumed characteristics that people are looking for when assessing who they are potentially interested in dating, which includes honesty, intelligence and passion (amongst others), and while I believe that I possess those and other desirable traits there is one important one on most people’s list that there’s no guarantee I will ever be able to fulfill; stability. I believe that as the number of years since we’ve graduated from college grows most people begin to put more of a premium on finding someone stable with whom they can rely on and begin a life with. However while I believe that I am a very loyal and dependable person my job ultimately comes first, which means that in many situations it seems as though I am not making my personal relationships the type of priority they should be.

Certainly I can’t argue this point, and perhaps the right person for me is someone who feels similarly passionate about their job; however, I can’t get past the idea that the choices I make concerning my job on a daily basis, and career from a long-term perspective, puts such parameters on my personal life and ability to maintain and grow relationships. Ultimately this is one of the sacrifices that I’ve decided to make in pursuit of my career aspirations, and I have never had second thoughts that this was the right decision for me. However, this doesn’t mean it always feels good or that it doesn’t bother me that the instability and uncertainty in my professional life makes it difficult for people to rely on and get close to me. In the end life comes down to a series of choices, and so much of the choices we make are affected most by their timing, so really all we can do it let things play out, do what we think is best for ourselves at the time and hope everything works out in the end.


Any Suggestions?

by RollingStone9862 under Online Dating,Relationships

The other day a female friend of mine who had recently joined JDate asked me to take a look at her profile in order to potentially identify any areas that she could change or improve. While I am far from an authority on what people should put in their profile I did agree to take a look at hers since I have a pretty good idea of what the average male is looking for when he reads through a woman’s profile. Unfortunately, the problem I encountered during this process was that I already think my friend is great and know pretty much everything about her, which ultimately caused me to read through her profile with rose colored glasses on.

However just because I wasn’t able to give a particularly helpful assessment of my friend’s profile doesn’t mean that having someone with a different perspective read over your profile isn’t a good idea. I honestly believe, whether it is a person of the opposite sex or not, that having someone who doesn’t know you, or at least doesn’t know you that well, look over your profile is a good idea because then they can make objective suggestions for how to improve it. In the end what you choose to include in your profile is 100% up to you, and no matter what anyone else suggests it is important you only include things in your profile that you are comfortable sharing and represent you in the best possible light.

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Would You Like To Meet My People?

by RollingStone9862 under Date Night,Online Dating,Relationships

I’ve gone out on a bunch of dates with a woman over the course of the last month, and during that time we have gotten along great and had a lot of fun together. This has led me to contemplate if we havereached the point where I should introduce her to my friends. Obviously I am well aware of how inexact the science of dating is; but I do think that there is always the potential for disaster (in the form of scaring someone off) if you introduce them to your friends too early. Sure, you could have an adult conversation about your relationship where you both get on the same page as to exactly how each of you feels about the relationship and where it is heading, but for most people, me included, that is once again a dicey area because you don’t want to have that conversation too soon either.

Since I’ve been thinking about whether it is the right (or even a good) time to introduce the woman I’ve been seeing to some of my friends , and have teetered back and forth, this has eventually indicated to me that I should probably not try to force it by specifically setting something up, and rather should just let an opportunity naturally present itself. Fortunately for me I didn’t have to wait very long since a few days after I reached the prior sentence’s conclusion a good friend of mine informed me that his birthday party was going to be the upcoming weekend. Immediately I figured that this was the right opportunity to introduce her to some of my friends since the setting would be very casual, and there wouldn’t be much pressure since there would be a large group of people – many of which I won’t even know. Last night I invited her to the party via text since she is out of town for work and that is the primary way that we have been communicating, although her response of “sure” was less than enthusiast; but I have tried not to read too much into it since, after all, it was in a text message.

Ultimately we’ll have to see how things end up going this weekend, and whether or not she was actually ready, and wanting, to be introduced to some of my friends. Since asking her I have tried to put myself in her shoes and think about how I would feel is she had invited me to a birthday party this weekend for one of her friends, and I can honestly say that I would be more than happy, although a little nervous, to go. When it comes right down to it during relationships you have to take leaps. Over the course of time many of these leaps will inevitably seem scary, difficult or not quite right at the time; but in spite of those (and other) apprehensions we might feel we still need to take them because those leaps are what fuel a relationship and bring two people closer together.


I Just Messaged To Say Hello

by RollingStone9862 under JDate,Online Dating,Relationships

I think the unwritten rule that once you leave college you can’t make a new friend of the opposite sex is complete bollix. I understand that, as a single male, I am much more apt to view every woman I meet in terms of her romantic potential but I am very sick of viewing woman, and our interactions, this way. Case in point, as I’ve mentioned numerous times in past blogs, I haven’t gone out on what I would consider to be a bad date in over a year. That being said, however, I haven’t been interested in going out on many second dates, which has left me in a bit of conundrum.

You see, I’ve gone out on a bunch of dates with women that I didn’t feel a romantic attraction or connection with, though I would have loved to continue hanging out with them as friends. I know that this would be a much more reasonable request if I hadn’t met the women in question on a dating site, since then we wouldn’t have met under the sole pretense of seeing if we were romantically compatible. Yet, I still wish there was some wiggle room within this construct that would allow us the opportunity to become friends.

Recently I was on JDate scanning the list of women who were online and I noticed a woman that I had dated last year for about two months was logged on. Our relationship ended amicably with both of us agreeing that our schedules were too conflicting and that we just couldn’t make things work. However, I’ve always felt that, had we met under different circumstances, without the burden of expectations which dating someone brings, we could have become really good friends. Of course, when we decided to stop dating we both wished each other well. Still, I am someone who believes you can never have too many good people in your life, which is why I was tempted when I saw her online recently to say hello and ask how she was doing.

Of course I know that this is a big online dating no-no since, once you cease dating someone you’ve met online, you are supposed to cut ties and go back to the proverbial dating grind. Yet, I don’t like underlying reality to online dating. Having that been said I don’t know how I plan on changing it since I might be leading the way in this revolution without anyone marching behind me. I did want to get these feelings off of my chest. In the end there are many aspects of online dating that I enjoy and am thankful that it is a resource for meeting people which is available to me. Ultimately I know you can’t always have things just the way you want them when it comes to dealing with the uncertainty and unpredictability of dating. On this one subject, however, I do wish things were different even if I’m being way too idealistic in my outlook.


What To Wear, What To Wear

by RollingStone9862 under Relationships

When I go out on a first date I always think about what planning elements, within my control, will most help me make a good first impression. Certainly finding an agreeable time and place to meet are at the top of my priorities list; but other components, such as how I present myself, are also exceedingly important to consider.

I believe wholeheartedly that it is imperative to be yourself on a first date, which includes what you say, how you act and how you present yourself aesthetically. Everyone, whether they profess to care much about their outward appearance or not, has a style that is uniquely his or her own. For me, generally speaking, when I go out I dress up in one of two ways; 1) jeans and a concert or graphic tee or 2) jeans, button down shirt and tie (loosely tied of course).

Of course there are variations of these two specific styles that I’ll use from time to time to alter my look; for the most part these are the main two presentations that I prefer when I go out. Both say something about my personality – that I’m laid back but definitely care about and put time into my appearance, and also that style is important to me.

This is not to say that if you typically wear sweatpants and a plain white t-shirt everyday that you should put on a collared shirt and khakis just because you have a date because that wouldn’t be projecting the real you. Personally I am not a real big polo guy, therefore, even though polos are very standard for guys to wear on dates, you’ll rarely see me wearing one because that’s not my style and therefore I wouldn’t feel completely comfortable.

In the end, what you wear is just another element that contributes to your overall ability to feel like, and therefore be, yourself. So, even if you aren’t someone who normally cares about their appearance I would encourage you to take a few extra moments in order to make sure you aren’t trying to present yourself in a way that you think will appeal most to the person you are going out on the date with, and instead simply showing off the real you.


Will Someone Please Get Me Some Food?!

by RollingStone9862 under Relationships

I always experience one constant feeling after a date, no matter how well or badly it went. That is, an intense feeling of hunger. Since I work late the earliest I am able to meet for a date is 7:30, but on some occasions it can be as late 8:30 or 9:00. Since I typically go out on dates during the week this is often times too late for the woman I am going out with to eat dinner, therefore we usually just grab drinks and, if I’m lucky, split a small bite.

I work on the far south side of Chicago, and every place I could conceivably meet a woman in order to go on a date is located north of me; therefore it is easy for me to always drive straight from work to a date.  Usually for a first date I like to suggest a place where we can comfortably sit, have a drink and order food if we want, but often times my dates will have eaten right before we meet and therefore won’t be very hungry.

Since I no doubt raced to the date straight from work – changing on my way out the door and, once in a while, doing my hair in the car to avoid being late – I always show up to dates starving. Furthermore, if the woman I am on a date with isn’t interested in eating then I never order anything because I’m just not comfortable sitting there stuffing my face when she’s not having anything to eat.

Of course, knowing that this is going to be the feeling that I enter every date with, I could make the necessary adjustment and either eat something on my way, or make sure that we specifically make plans to eat dinner during the date. Usually, however, I like to keep it open-ended and just go with the flow of the evening based on how we are both feeling. Unfortunately, a side effect of planning things this way is that if we don’t eat I have to go through the entire date hungry. Additionally, I realized recently that as a result of my empty stomach the effects of the drinks we have are magnified and therefore I need to closely watch my consumption so that I am able to drive home.

I know that this particular problem might seem silly, and most people reading this could list off the top of their head a half-dozen reasonable solutions; however this is the way that I am most comfortable approaching first dates. So, even though it doesn’t seem rational, I’m going to probably keep things this way, which means I’ll just have to suck it up if on my next date if we don’t order any food knowing that after it’s over I’m going to have to race home and make a frozen dinner.

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You’re Not Bad At Dating

by RollingStone9862 under Date Night,Relationships,Single Life

Sometimes I feel like I’m bad at dating. Some who read the previous statement might think that it is ridiculous for me to feel this way because so much of dating comes down to chance and timing; however, every once in a while that’s just how I feel. Perhaps I am just getting frustrated that I’ve been consistently going out on dates for about a year now and haven’t met someone with whom I’ve become seriously involved with, but ultimately I know that really isn’t necessarily because I am not doing anything wrong or am bad at dating.

I think sometimes, whether it’s dating, work, or picking horses at the track, you get on a roll, your confidence shoots through the roof and, as a result, you feel fantastic about that aspect of your life – but what really makes that happen? With picking horses you can do more research, and at the office you can stay later, but what can you do if you feel like you are in a dating slump?

For one, you can go out on more dates, which is what I’ve tried to do. However, I honestly think that has exacerbated the problem. The more dates you try to go out on the looser your standards become for who you go out with, which potentially opens you up to more issues because you are going out on dates with people you probably aren’t compatible with. There’s an analogy we use in basketball that you can practice free throw shooting all day but if you shoot them the wrong way every time you’ll never get any better, which is, unfortunately, how I feel with dating sometimes.

Ultimately I know that it’s not that I’m bad at dating, but that perhaps I’m replicating the same mistakes on each date. Whether this is true or not, short of videotaping my next date and then breaking down the film afterward to identify what the good and bad elements of my performance were, I guess all I can really do is try to go out on dates with women I truly believe I’m compatible with, be myself during our them and then hope it all works out in the end.


This Is Just Real Talk

by RollingStone9862 under Relationships

Alright, that’s enough, both sides stop it! Stop it right now before someone really gets hurt!

Guys – if you go out with a woman, and don’t want to see her again, then don’t make ANY indications that you are going to call her. Because when you do that, you lead her on, and that leads to the development of expectations and her eventually being let down.

Ladies – if you go out with a guy, and aren’t interested in going out with him again, then just say so.  Please don’t say that you want to go out on another date in order to “spare our feelings,” because we all know you really aren’t doing it for us.

You see all this game playing and posturing is nonsense! Utter nonsense!

How old are we?

At 27 I consider myself to be a “big boy,” and think I am quite capable of handling the rejection that results from being turned down by a woman for a date. However, when I do begin to lose my patience, and act like a baby, is when women tell me they had a great time and want to go out again but never return my calls or texts trying to make plans.

I am fully aware that on the other side of this, women experience the same frustrations when it comes to men saying, at the end of the night, that they’ll call them, but never do; which is why I am calling out both sexes in this piece.

So just stop it. Stop all the game playing and rhetoric because that leads to people being led on, which I promise you hurts them more than if you would have just nicely rejected them in the first place.