Recently, I was having a very nice email conversation with a woman that I had met on 100hookup. We had sent emails back and forth expressing some of the things going on in our lives, some information about our jobs and interests as well as other random factoids which gave the other person a glimpse into our everyday lives and personalities. In fact, our interaction was going so well that after sending my third email I decided in the next I would ask her out on a date, assuming I got the vibe that she was still interested.

However, before I proceed with my story, I need to give a little bit of background on my third email. In the opening paragraph, in response to her telling me about a job she had just gotten working with special needs children, I commented, “One of my best friends is a teacher’s aide for special needs children at a school in the north suburbs and she loves it.” I then went on to ask some questions, including if she had anything exciting planned for the upcoming weekend.

With the sending of this email I had the utmost confidence that the conversation was going to continue, and that I hadn’t said anything controversial which might derail my chances of getting a date. Unfortunately, what I failed to consider was that I had casually brought up, without any context or previous mentioning, that one of my best friends was a woman. Therefore, when she responded to my third email with her opinion that men and women couldn’t be close friends, I was quite confused by what had prompted her to express such strong opinions on the subject.

While I understood her perspective that it is sometimes difficult for men and women to be close friends (due to a perceived, and sometimes real, underlying sexual tension between them), I felt like it was unfair for her to make that assumption with me. Furthermore, even though I did feel badly about the way she reacted, it was good that she expressed her opinion; had we started dating, this would definitely have been a point of contention later on since I have many close female friends.

In the end, my casual reference to a close female friend raised a red flag in her mind the same way that her reaction to it did for me. That’s why, ultimately, I realized that it’s better to go with the normal flow of conversation; don’t over think or script the perfect things to say to someone you are just getting to know.  I have many close female friends that I have no interest in dating, and have zero interest in dating me. This being said, however, I still think I’m better off putting the information out there, and letting the women I talk to decide for themselves. After all, everything comes out eventually.

Dear Tamar,

I’m having a hard time writing the “about me” section on my profile. I’m not really sure what to say. I want to sound interesting but at the same time also fun and cute. Can you help me on what I should say? Thank you!

Dear Profile Help,

My suggestion would be for you to start with making a list of your best qualities and a list of what you are looking for in your beshert. Now, many of these things are mentioned later in your profile in the fill-in-the-blank and multiple choice sections, so make sure you don’t simply repeat those things but expand upon them. Make sure your first line is catchy but not corny and make sure to mention things that make you unique and set you apart from the pack. Double check your grammar and spelling and make sure not to write too much, this isn’t your autobiography. You want to sound intriguing but leave them wanting more. Here’s an example:

I’m a 27-year-old journalist who loves having fun and being funny, even if it’s at my own expense! A guy who can’t laugh at himself is definitely not the right guy for me — and sarcasm is a plus! I like to go out but I also really enjoy a nice night just hanging out at home. I’m looking for a man to be my lover and best friend, a guy who will make me laugh every day, and someone who will bring out the best in me as I hope to do with him. I refuse to settle but am definitely realistic about my expectations. Oh, and a big bonus if you own the complete 10 seasons of Friends!

Dear Tamar,

I met a senior citizen on 100hookup 4 yrs ago — I am also a senior. We see each other 3 times a week, speak to each other a few times every day and share things with each other. He just sent me a birthday card expressing what a wonderful friend I am and how invaluable I am in his life. According to him, there is nothing in life to be valued like a friend. Every time I hear that word I cringe.  Am I wrong?

Dear Friend or Foe,

Are you wrong? In a word, NO. But unfortunately it’s not so simple. Four years is a long time to be spending with someone, whether you’re in your late-30’s and your biological clock is ticking or a septuagenarian and that “other” clock is ticking — why waste precious time with someone if they don’t like you as more than a friend? Go ahead and cringe, I understand.

If the card is the only thing that concerns you, then simply mention it to him or leave it be. But if there are many more signs where that came from, than do yourself a favor and reactivate your 100hookup membership. Are you looking to get married again or for companionship which includes moving in together? Because after 4 years one of those options should be in progress by now. Regardless of what you want from him or what you expect from him, after 4 years you deserve an explanation.

Recently 100hookup passed on to me some fan mail. This is significant because my blogger moniker is different than my profile moniker so it is a little hard to locate me (shhh).  Well, I’m flattered.  Who knew MOTs followed the blogs.  I’ve never claimed to be a therapist, a dating expert or the like.  I’m just a thirty-something caught between the Moon and New York City (name that movie/song for $100 bonus) looking for her Lobster (as Ross so eloquently put it on the TV show Friends).