I went on my first 100hookup date a few years ago.  It was the easiest date I ever got.  All I had to do was look up girls of my age in my area, and then contact them.  This is something that would have not been possible if the only tools at my disposal were myself and the world around me.  I had lived 20 years with myself and the world around me, and the world was not enough.  The world has these barriers that are often close to impossible to break down.  For example, how do you walk up to a girl you do not know and not only talk to her, but maintain a conversation that is interesting enough to sustain her interest without having to pay her?

I was still on my high from joining 100hookup, and figured that since it was so easy to get a date, the date itself would be equally simple.  Therefore, I sort of half-assed it.  I didn’t dress up very nicely.  I only brushed my teeth twice.  I didn’t wear cologne (although I never wear cologne).  As a side note, sometimes girls don’t like dudes in cologne.  Is that a correct assumption, or have I been making a horrible mistake my entire adult life?  Anyway, I didn’t put much into preparedness.  What I didn’t realize was that I was about to meet a person with all of the complexities and intricacies of any carbon-based life form.

Five minutes into the date, I had nothing.  I actually tried to see how much time I could take up by laughing for no reason.  Then, I decided that she would be the perfect guinea pig to hear material I was planning on using for my amateur stand-up comedy debut.  After I had exhausted my five minute routine, I figured that I would use the date as an opportunity for a free psychiatric session.  I told her all of my insecurities and fears.  After the date, which involved a little bit of drinking, I figured that I had just conducted a perfect rehearsal of male to female interaction. What I didn’t realize was that in the previous scenario, the male would be akin to a crazy homeless person, and the female would most closely resemble a woman sitting at a broken traffic light after having given the man a dollar without realizing she’d be sitting there for a long time.  She had given me the dollar, but I insisted on annoying her until the traffic light was finally fixed.

Dear Tamar,

I recently accepted a Sunday brunch as a first date from a widower. He mentioned that a year had passed since he’s become a widower and he was seriously seeking a partner to share his life with. He also made remark about an upcoming dinner date where a woman was going to meet some of his friends. Aside from this awkward comment, the date was lovely and as we parted he suggested a second date.

Another weekend passed, phone calls and emails when finally a date was proposed by email but not for another two and a half weeks, again on a Sunday but this time for dinner. He seemed like a relatively normal guy, so accepting the date wouldn’t have been out of the question except clearly I’m not at all on this man’s dating radar with a month between dates selected on Sundays.

Should I just say I’m unavailable, not answer, or acknowledge that he find me if and when his dating schedule opens up? I certainly understand dating a number of people simultaneously as you attempt to find the one, I do likewise. But he’s asking me to make an hour long trip back and forth on a work night when I’m obviously not a priority. It seems incongruent.

Dear Inconsistently Interested,

I think you already know the answer to your question, otherwise you wouldn’t bother asking, right? It sounds like you just want reassurance that rejecting the date is the right thing to do. But, and this is a big BUT, it is possible that he was dating someone, it got serious but didn’t work out, and now he’s getting back in touch with you because he felt a connection. You could accept the date but go on it knowing not to expect much and hopefully be happily surprised. It sounds like this guy caught your fancy so if you’re still unsure just ask him what’s going on. He may be surprised by the question and you may not like the answer, but if it’s going to continue to bother you then why not ask? Good luck!

I wake up at eight o’clock in the morning on a Saturday.  My first date with this new girl will be happening in twelve hours.  I spend the first hour lying in bed sweating.  Hour two is spent trying to fall back to sleep whilst concurrently batting away thoughts and feelings of inadequacy and a poorly conceived tattoo that I have to remember to cover.  Hour three is spent shaving my arms so my tattoo will be visible as an ice-breaker when awkward silence will inevitably come within the first two minutes of inception.  Hour four is spent ruminating over the fact that the activity spent during hour two and the activity spent during hour three are completely contradictory.

Hour five is spent finding a way to eat something without spending any money, as I must conserve all currency for tonight’s rendezvous. The first three minutes of hour six are spent trying to go run for the first time in a year.  The next fifty five minutes are spent crying to myself while trying to walk.  Hour seven is spent playing Tetris®, as it is the one activity in my life where all of the pieces fall perfectly into place.  I can’t find where to fit a piece and inevitably leave a hole.  I stop playing Tetris.  I start playing Tetris again because I still cannot stand up fully due to activities completed in hour six.  Hour eight is spent panicking as I try to remember my date’s first name.

Hour nine is spent showering, washing myself obsessively until I either run out of soap or my hands start bleeding.  Hour ten is spent trying to stop the bleeding.  Hour eleven is all about cologne.  Hour twelve is spent yelling at my car’s GPS as I get completely lost within one mile of leaving my house.  Hour thirteen is our date. How do you prepare for a date?

Sometimes I have to remind myself that dating, and meeting someone is, in its most basic form, a process of trial and error. You never know whether or not the person you’ve decided was attractive or interesting based on an initial interaction at a bar, or from reading his or her online profile, is actually going to be someone who will elicit a spark.

You see, when you think about it, most of dating comes down to reading people and looking for subtle clues that give us little insights into the other person. Often times on a date I can tell within minutes of our meeting whether or not we have a spark. Perhaps you think this is silly or trite, but I always try to trust my instincts, and when it comes to judging whether I am interested in someone romantically I am rarely wrong.

I believe this is due to the fact that I approach every date with an open mind and clear perspective. Because really, when you think about it, the idea of a first date leading to a second date, and one day even developing into a relationship, is an awful lot to have weighing on your mind heading into every first date. So try to take the pressure off yourself, and know that things may work out, and things may not, but in the end what matters is that you are trying to meet someone because, without trial, there cannot be error… but there also can’t be success.

Dear Tamar,

Hi! I’m new to the whole online dating scene. Right now I am talking to two girls at the same time and I am not sure whether I should take them both out on dates or just one. Should I take one girl out on a date and stop speaking to the other girl even if I’m still interested in meeting both? Thanks!

Dear Two Timer?,

“Meeting” a girl on 100hookup does not a relationship make. I am a strong, strong advocate of poly-dating until it gets serious with one person. First of all, you may pick one girl and have no chemistry with her and now you’ve already ruined your chances with the second girl. Take them both out on dates, try to be unbiased and not compare them to each other, and save any decisions until after each date. There may be no attraction, no chemistry, or it may not be mutual with one or both of the ladies. Keep your options open at all times. Between when you “meet” a girl on 100hookup and when you actually meet her in person, you may “meet” even more ladies online… and guess what? That’s great! If you were able to meet that many great hookup gals at a bar then 100hookup wouldn’t exist, but the fact is that you can’t; no one can, which is why 100hookup is so successful. Take the opportunity to meet as many women who fit your preferences as possible because the more women you meet the better your odds are of finding your Beshert. Good Luck!

It’s funny because, no matter how old I get, or how many dates I go on, after a really good one I always call my friends afterward to tell them about it. I don’t care how guys are supposed to act after a date, or what is perceived as “playing it cool” because if I go out on a good date, I will call my friends after to talk about it like an excited schoolboy. I mean, as human beings, it is only natural that after we have enjoyable experiences, we feel a strong desire to share them with those closest to us.

Recently, I went out on a third date with a woman that I had met on 100hookup; on the first two we had gotten along really well and both had a good time. Since we had met for frozen yogurt on our first date, and gone out for sushi on the second, I wanted to do something a little different for our third date. After thinking about our options for a Wednesday night, I asked her if she was game for grabbing dinner at this offbeat pizza place and then going to an Improv club for a show.

She responded that she was “up for anything” and we agreed on a time that I would pick her up on my way back from work. The pizza place was just down the street from the club so we grabbed some macaroni and cheese pizza (delicious), and chicken fettuccini alfredo pizza (yummy), before heading over to the show. The first act was a little a hit or miss with the performance since they were a newer group, but the second team more than made up for it and was absolutely, side-splittingly, hilarious!

After the show we talked for a little bit before I dropped her off and we said goodnight. However, by the time she made it inside her building, I was already dialing a friend to talk about the date. Once we got off the phone I quickly dialed another friend and it was after we hung up that it dawned on me that my wanting to immediately call my friends after a date was a sign that I was excited because it had been really great.

Undoubtedly, other people have different subconscious indicators that tell them they had a fun time. If you don’t know what yours are then I encourage you the next few times you go out on dates to think about what were your immediate natural reactions afterward. Often times, after going out on date after date, we try to fool ourselves into thinking that a date went better than it did. However, it is in these situations when we can rely on our post-date indicator to keep us grounded in reality by telling us the truth about whether or not it truly went well.

You are going to meet people on 100hookup. You are going to talk to the people you meet and, in some cases, you are going to have an extended interaction with them that leads to a date. In those cases, if you are like me, you’re going to get excited and eagerly anticipate that first meeting.

Depending on the particular situation, a first date might range from simply meeting for coffee to grabbing a nice dinner to even something more ambitious and unique like going to an exhibit or attending a concert. Even though each couple is going to make different choices regarding how they construct their first date, when it comes down to it, they’re meeting and that’s all really all that matters. Especially since getting to that first date isn’t always easy.

Many online conversations start out as promising but never seem to find exactly the right rhythm that keeps them going and elevates them to that next level. However, you can’t be deterred by this online dating inevitability (and others like it), and must stay the course by remaining active in trying to meet people. It is that attitude which ultimately makes that first meeting so fulfilling.

But what happens if the night before, or day of the big date, the other person cancels?

This scenario happened to me several times before I even went out on my “first” first date with someone I had met on 100hookup and I’ll be completely honest when I say it doesn’t feel good. No matter how legitimate the excuse sounds, no one likes to have the rug pulled out from under them, especially in a situation that they were looking forward to, and had put a lot of time and energy into setting up.

I’ve had women cancel on me for a variety of reasons, including having to babysit for friends, forgetting about a friend’s graduation they promised to attend, bad headaches and some others I can’t even remember anymore. However, in spite of the fact that some of these excuses were probably true, the point still remains that it sucks to be cancelled on.

Unfortunately having people break plans that you were excited about is a part of the online dating game and is, therefore, pretty much unavoidable. Putting up a profile on a dating website and thus proclaiming to the online dating community that you are single and looking to meet people is the first important step, but you need to stay committed and not dwell on the disappoints that pop up along the way. I promise when you finally get to that first date, and everything about it feels right and natural, you’ll be glad you didn’t let a few broken plans deter you from trying.

It is really popular for people, in general, to say that going to the movies is an awful way to spend a first date. But I think that going to the movies can be part of a great date. Please note that I am often wrong, and have been on many terrible first dates.  This being said, however, I stand by my ridiculous claim.

Of course, just going to a movie can’t be a whole date.  I do believe, though, that it can supplement dinner, or another imaginative, phony, impromptu activity.  You can go out to dinner first, which everyone agrees is a satisfying shared activity. If the dinner goes well, you can offer to take your date to the movies.  If he/she says no, that’s okay.  But if he/she says yes, then it is on.

Even if dinner proves to both parties that the date was a mistake, a movie is a nice way to not have to talk to the other person for the rest of the night.  You can live vicariously, for about two hours, through the lives of the more attractive characters on the screen.  Go pretend that it’s you extracting information from another man’s dream, or get mistaken for a criminal while on a nice dinner date with your wife. Ahem, Tina Fey.

However, if dinner goes well, then the movie experience will prove even better.  Once you’re at the theatre sitting in your comfy, reclining chairs with optional armrests, it feels great.  The air conditioning is usually on high.  You’ve already (hopefully) shared fulfilling conversations, so now you can relax.  It’s okay to sit back and unwind.  You don’t have to talk for the entire date; sitting while not talking will probably comprise a good portion of your marriage in the future, anyway.  Might as well sit back and enjoy yourself.

My friend Miriam* called me for advice the other day. She met a guy 100hookup but things haven’t exactly gone smoothly. He sent her the initial email on 100hookup which was good and after exchanging a few e-mails he asked her, still via 100hookup e-mail, to meet him for a glass of wine. She responded with her phone number. His response: his phone number. Obviously, they didn’t meet because someone had to make the first phone call, right? After a few more e-mails throughout the weekend he again asked her to meet, this time for gelato. She responded with her phone number. His response: a text. The non-existent relationship went from confusing to annoying.

She told him she wasn’t a text person, but he told her he wasn’t a phone person. It was enough to make a girl give up and Miriam was just about to throw in the towel. I advised her to stop playing his game and not respond to his texts. It worked. He finally called the next day to ask her out. Finally, they met but all that effort was wasted as it wasn’t meant to be. I doubt this guy is going to find his Beshert if he continues to be difficult and communicate with women in this bizarre way.

*all names have been changed

Julie* recently went on a 100hookup with Brian, a good looking lawyer who recently moved to town. Unfortunately, the report was not good. Yes, Brian was handsome and smart, but no, he’s not an avid conversationalist. This guy didn’t know the meaning of biting his tongue or having restraint — he was an open book but Julie had barely read the back cover. The more he told Julie about himself, the less interested she became.

Brian proceeded to tell Julie all about his entire life over the course of one drink and one hour: his father’s six ex-wives; the medicines Brian takes for OCD and ADHD; his dyslexia; his skin rashes; his likes and dislikes; and finally – the kicker – his ex-girlfriend. None of the items are particularly funny when heard separately, but when taken altogether it was a dark comedy that had come to life.

Maybe Brian was trying to put all his cards on the table and let Julie know exactly what she’s getting into, but his technique needs some major help. Of the above list, the only topic that should be discussed during a first date is your likes and dislikes. 100hookup makes you feel like you know someone better than you really do before you even meet, but remember that the person sitting across from you is still a stranger. The prescriptions in your medicine cabinet are not something you would discuss with the person sitting next to you in the doctor’s waiting room, so why share it with a girl you’re trying to impress?

One of the reasons I suggest meeting your 100hookup matches right away is because you need to maintain some semblance of normalcy when it comes to conversation. You have the topics right in front of you when you look at their profiles, so use it to your advantage and keep to the typical first date conversation topics within those guidelines: why did you choose to go to [college]? Where did you grow up? How did you get started in your career? Stick to the basics and censor yourself before divulging information that is, to put it bluntly, none of your date’s business right now. On the first few dates, regale your date with funny, positive and interesting stories about yourself and leave the deeper, sad and bewildering stories for later on in the relationship. Hopefully you will be charming enough with the former to leave plenty of time for the latter.

*all names have been changed