After a countless number of first dates (47), I had decided that I had to do something about my self-esteem before my self-deprecatory comedic nature led me to laugh with my friends about how much of a loser I am until my thin veil of happiness melted in a fit of unbridled rage against people that formerly would have identified me as a friend.

I needed an ego boost. I am not happy or proud of the way I tried to do so. I decided to accept a date with any woman. I arrived at the restaurant early because I was still nervous. As I sat there looking at the wait staff who had to have reluctantly agreed to all wear horrible Halloween costumes, I figured that nobody in this restaurant except for the old man drinking by himself was truly happy. The date was pleasant. We had good conversation and the food was equally pleasant. Though I was not attracted to her, and her voice reminded me of my step-sister, who I like, but I do not want to date, she was very nice. The day after the date, I received a text that I had previously sent out 47 other times. It said she had a great time and wanted to hang out again this weekend.

I knew exactly how she felt at that moment, and I know exactly how she would feel if I didn’t respond. It is one of the worst feelings I’ve ever experienced. It’s just complete rejection after pouring your heart out for an entire evening to a total stranger. You stand by your phone waiting for that buzz that never comes. You can’t eat or sleep, and getting up for work is even more of a chore. I had to send her something, but I did not want to go out with her again. Next week, I will tell you what I eventually said, and how she responded.

So I had two dates scheduled for last weekend. That’s two dates. To put this enormous number of dates into perspective, the amount of dates I was supposed to go on last weekend outnumbered both the amount of dates I’ve gone on in the last year and the amount of times I shower consecutively before I go out on one date.

I was nervous but extremely excited going into last weekend. I had ideas for what I was going to wear on both evenings. I meticulously planned both dates. I received a text on Thursday that my date for Saturday had to reschedule. It was a little upsetting, but I was more excited about the Friday date, anyway. I couldn’t sleep Thursday night, and woke up at roughly 3 am. I saw that I had missed a text from the night before that basically said that my Friday date also had to reschedule. I spun into a deep depression. I barely made it into work in the morning. My OCD was kicked into overdrive, and I imagined that I would never meet another girl again. I was sweating profusely and shaking violently.

After a bad several days, my first rescheduled date went off well. We went to dinner and I listened, talked slowly, and used good manners when eating a panini. Wow WordPress just told me that ‘panini’ is not a word. My delicious Monday night sandwich would not be pleased with this information.

Anyway the date went well. Since I had not managed to make it to a second date in a very long time, I was really anxious to hear if she wanted to go out again. I texted her a few days later. Wow, ‘texted’ is not a word, either? Anyway, she didn’t write back. I freaked out and convinced myself that no woman would ever love me. I quickly texted a girl whom I had gone on one date with six months ago and never called. Though she was somewhat friendly, I just had no desire to go out with her again. Basically, I was asking myself out on a date with a girl I didn’t like simply because another girl hadn’t answered my text yet. After the date with the girl I didn’t like was confirmed, I finally got a text from the other girl saying she’d like to go out with me again. At least my weekend is full this time.

Just got a new phone number online?  Haven’t met yet?  Haven’t even talked on the phone yet? Grab that smart phone and start texting! 

These days texting is an essential part of online dating.  It will help you get to know the person you are with for a long period of time.  While you spend days randomly texting here and there, the comfort levels will increase and go way up.

By the time you meet for a first date, comfort levels will be so high that it will not feel awkward or like a blind date at all.  Run your messages right and you may even feel like you have already been dating for a long period of time.

How often should you text?

Don’t overdo it.  Remember, you don’t know each other yet, so you don’t want to come across as creepy or stalkerish.  A random text here or there will get the job done. 

More on what to text in the next entry!

I have been on a cold streak (10 years) when it comes to dating. I am really good at meeting my date. I say, “Hello.” and listen to her answer. Then, I conduct myself as a normal human being interacting in a way that employs both my verbal and physical abilities. I listen to her talk and answer accordingly. I laugh when she says something clever and cast sympathetic eyes when she tells me something sad. I sit and hold back my conversation in order to let her speak more about herself. I also offer to pay if we are patronizing a place of business. If she insists, I let her pay for because a.) I have almost no money, and b.) I want to show her that I’m progressive, too. I am so progressive that I’ll let her pay for my entire meal.

Though I think I am handling myself well and carefully, I don’t think that I look and sound like what I think I look and sound like. What, to me, seems like genuine laughter at one of her anecdotes may, in fact, look like a crazy person punching the table and kicking wildly while laughing two octaves higher than most humans can speak. What, to me, seems like pensive thought while she shares something somber, instead, looks like utter confusion and profuse sweating. As I sit and try to listen, I seem to laugh intermittently at just the right moments and at just the right volume. Though, in reality, this looks like a manic seizure that years of therapy and Xanax have not fixed. Though I think that I am being progressive by letting her pay, I am in fact regressing the date back to 1955 when the woman was in charge of feeding her man.

I am now at a point where I feel a strong compulsion to text the girl immediately after every date because I am so afraid that she will never want to see me again. I know I shouldn’t do it, but I feel such a strong urge to do so. Tonight, after another first date that I thought went relatively well, I texted her about twenty minutes after the date. This time, she said she’d like to go out again. I wonder what a second date is like.

My first date occurred in 1998. It happened, relevantly, at the local JCC. There was some sort of social thing for kids, and we must have hit it off. Of course, we must have hit it off in a very 14-year-old way. I must have been the guy wearing the silkiest of all the shirts. Of course, this was 1998. 1998 I looked like Ben Affleck,not Daredevil Ben Affleck, but School Ties Ben Affleck. I would have changed teams for School Ties Ben Affleck.

After the party, we talked several times on the telephone. We decided to meet, of course, at the JCC. First, we went to the snack bar, and then had an intense hugging session in the basement. For you purists who may claim that there are no basements in Texas, this is a very odd-shaped JCC and the bottom floor was semi-underground. I’m not crazy, this date actually happened.

Our second date was at the movies. Remember, this was the movies of 1998. There were none of the modern amenities that we often take for granted today. Namely, the armrests did not lift. We made the best of a bad situation and it made for a wonderful viewing of The Apostle starring Robert Duvall. Of course, once she got to actually know me, I was headed for a lifetime of loneliness. I did not know how to extend a conversation past “Here is the basement of the JCC.” I also did not know how to interact around her friends. I think we went to the science museum once. I also vaguely remember that the boys were into cars. I had no idea about either of these topics. Sadly, she broke up with me over the phone while I talked to her from my bedroom. One day I will have a car of my own. She’ll see! They’ll all see!

So many men seeking online dating advice come to me with the same story…

They go out on a first date…

Everything seems to go absolutely perfect.

They have fun, enjoy good conversation, there is heavy flirting, some casual kisses, and even planning for a second first date that takes place..

And then NOTHING.

The girl disappears, never to be seen again.

So what on earth happened?

1.  We may not be being honest with ourselves.  But if the date resulted in kisses (Pending they weren’t over the top sexual) and plans for a second date were made, odds are that it probably is not that and the date did actually go well.

2.  The female is just flaky, plain and simple.  One of the problems that is inherit with online dating is that it creates a strive to find absolute perfection.  Women just never ever stop getting new messages.  They may have even received 20 new messages since the time your date ended, to when your first phone call was made.  Some of these women just keep dating new people no matter how good their first date was because they are always looking for something better that may not be out there.

My advice, just go with the flow and don’t start building houses with white picket fences until you are sure you found one that is ready to commit!  It may just not always be your fault!

Have you ever told a story on a date you thought was funny/interesting/unique/heartfelt/etc only to never hear from your date again? Yeah, don’t tell that story on 1st dates anymore. Live and learn. You know which stories I’m talking about, the one about your parents eating so many carrots that their palms turned orange (real line I heard from a guy), or the one about your family of sleep walkers who’ve all gone to the bathroom in rooms where there isn’t even a toilet (a friend who will remain unnamed), or the one about that date you went on where the guy had a long thick hair growing out of the tip of his nose (a date I went on). None of these stories need to be told on early dates. Don’t tell stories about how your family is odd just yet, don’t talk about dates you’ve been on and don’t talk about anything having to do with the bathroom. Talk about you. The best you. Leave the embarrassing stories for later… there will be plenty of time, believe me!

I think after you break up with someone you have been going out with for a while it is difficult to get back into the flow of dating again. After going out on first date after first date you finally met someone that you felt a connection with, only to have things end, putting you right back in the same spot you were before that relationship began.

To some people first dates are an exciting adventure where you are getting the chance to meet someone for the first time and see if they spark that fluttery feeling in the pit of your stomach that we are all hoping for; although if you have gone out on as many first dates as I have over the past year then perhaps you feel, as I now do, that the first date isn’t as fun as it used to be.

Since most of my first dates have ended in romantic disappointment I have now tempered my expectations back so far that it is difficult for me to even imagine one going well. Additionally, since so few of the first dates I’ve gone on have led to relationships, and the ones that did were spaced out, it is nearly impossible for me to believe that lightening could strike twice in a row and I might be able to immediately jump right back into another relationship.

However regardless of my skeptical and, to an extent, self-defeating attitude when it comes to first dates I don’t want to impose limitations on myself as to when I get back on the horse. Maybe it will be a week before I meet someone that I want to ask out, or even a month; however I know that I am going to go out on another first date at some point soon, and when that day arrives, just like every other first date I’ve been on, I’ll just have to see what happens.

Dear Tamar,

How do I look past a bad first impression? I’m a divorced mom and I met a divorced dad on 100hookup. We’ve been dating 6 weeks, but I can’t forget what happened on our first date – while on our date at a restaurant, he touched me in an inappropriate way which made me feel very uncomfortable. I’ve continued to date him and even like him. He’s met my family and they thinks we’re a great match, but I still can’t forget the embarrassment nor can I understand why he would do such a thing as to be so awkwardly intimate with me so soon. He hasn’t done anything weird since and I really want to get over it but I can’t forget it. How can I move on so we can get more serious.?

Dear First Impressions Last,

Unfortunately for your date, you can only make a first impression once but, fortunately for him, (and unbeknownst to him) you’ve conceded by seeing him for the past 6 weeks. My advice is to tell him, in a joking tone, that he should never do said act again and let him know in a teasing way that he should know how lucky he is that you gave him a second chance. Allow him to respond and then drop the topic, forget about it and start making new memories to replace that one awful one. If you really want something with this guy you need to confront the situation head-on.

Remember that people are often extremely nervous on first dates, want desperately to make a good impression and therefore can make complete fools out of themselves instead. If you want to make this work then chalk his behavior up to first date jitters and excuse the act. When you’re not the nervous one it’s easy to forget that the other person might be. Ultimately you have to weigh your pros and cons when deciding if you’re going to continue seeing the other person – is the awkward act bad enough to stop seeing the guy? Aren’t people allowed to make mistakes?

In your case, it wasn’t bad enough behavior to stop accepting his dates, so what are you afraid of? Do you think he’s going to continue doing whatever it was he did or possibly do something else that embarrasses you in public? Are you thinking that he has tried this on other first dates? Are you afraid that was his true self? Or are you just looking for some kind of fault in him so you can put up your guard and stop yourself from possibly getting hurt? None of these questions can be answered without first casually confronting him and then next looking towards yourself to see why you might be intentionally ruining a good thing.

When you find yourself in doubt wondering if there is a fault you can overlook there are two things you can do. First, listen to your instincts and second, try to look at your situation from a different perspective and see if it’s really as awful as it is from the inside because it’s probably not.

My friend Julie recently a met a guy I’ll call “Darren” on 100hookup. It turns out they have a mutual friend who endorsed the match and the two were on their merry way to a first date. They met for drinks and Julie says it was a great time — there was constant and natural conversation, there were plenty of commonalities and there was mutual interest in seeing each other again.

Darren texted Julie the following Thursday morning and then called and asked her to go to dinner and a play on Saturday night — Prime Date Night! Julie was excited, needless to say.

Saturday night Darren picked up and then asked her where she wanted to eat. She was taken aback by the fact that he didn’t have any plans in mind, but she quickly rebounded and suggested a new place nearby. Dinner conversation didn’t flow quite as well as it did the week before and when the bill came Julie made a move towards her wallet, offered her credit card and Darren accepted. And as they were leaving the restaurant, entering and exiting the theatre, Darren not only failed to hold the door open for Julie, but let it fall shut behind him as he kept walking. The combination of all these faux pas was crushing as Julie was really excited about the prospect of Darren.

Julie was bummed but I convinced her to give Darren another chance if he were to ask her out again. A few days later she received a text from Darren saying that it was nice to meet her but they would be better off just as friends. Julie wasn’t so crushed because of the last date letdown, but still she was perplexed. I reminded her of the multiple faux pas he committed and pointed out that at least he was nice enough to not leave her hanging. We’ll never know what went wrong between date one and date two, nor why Darren wouldn’t give it one more shot, but he probably had a list with a few of his own grievances against Julie, faux pas that she committed unknowingly.

So how does something so promising fail so quickly and how can you keep these little disappointments from getting the best of you? Rollercoaster dating is unfortunately a normal part of dating and only hindsight will help you to see that the rollercoaster is actually weeding out the losers. And by losers I simply mean losing those that are not right for you. It’s better that the second date was such a doozy for both Julie and Darren because they didn’t waste any more time on something that ultimately wasn’t going to work out. Luckily, both of them saw the signs and neither was overly disappointed it didn’t work out. Maybe it’s realism, maybe it’s pessimism, but rather than getting your hopes up super high for each new date, try to just get your hopes up, say, medium high with a dash of sensibility.