I’m Arrow, Veteran Online Dater

Nov 09, 2009 • Arrow, Diary


I have a penchant for online dating. That’s not to say I meet women in real life–I would say half of my dates are from real life, the other half virtual–but there’s something fun about the whole online thing.

The anticipatory butterflies are worth it for one. That might sound hellish for some, however, the highs and lows they carry can be quite the ride. In your mind, you always hope for the best, whether it’s a date or something that should clearly be read between the lines. But as all things online go, things are not always what they seem.

A few examples to illustrate.

The Good: A date in Agoura Hills with a woman my age a few years ago when I was in my younger 20s. I drove out there, we went for food, a movie and came back to her place. We began to fool around and at some point I slipped in that I’d always wanted to pleasure myself in front of someone. I’m not sure why I said that, but I somehow knew she would be receptive. She was more than that, she was extremely excited. She cuddled aside me to watch from my perspective while occasionally nibbling on my ear. I came as she watched and she was soon wet, fingering herself. I went down on her, bringing with me her rabbit. She tasted sweet, unlike any other woman I’ve ever been with (her secret was her kumquat intake as she had a tree in the backyard). Her hips erratically moved about and she moaned until she came. Although she brought out a condom just in case, we were both satisfied and never had sex.

The Bad: Sometimes things don’t work out so well. After speaking online with a young hippie college girl with dreds for a few weeks, I made the trek out to Claremont to meet up with her. From the moment I saw her, it just felt uncomfortable. Her photos were not what she was in real life and honestly, I was not attracted, even if I tried. I attempted to be courteous and hang with her for awhile, but I lied when we were in her dorm room, saying I had never done this before and couldn’t go through with it. Eventually I left and the 60-mile journey to home was my mission.

Years later, I met an older woman online and convinced her to meet with me that same night. Eventually, I made it over to her Santa Monica home around 2 a.m. Needless to say, when she opened the door wearing elastic-band tiger print pants (I’m sure they felt comfortable), I knew this was bad news. Her photos were from a different era, that’s all I’m saying. Since I made the trek out, I decided I would hang out for awhile, but that may have been the wrong move. Another wrong move, let her give me a massage. I mean, hey, I love massages, who is to give a good one up? But the problem was is that she got weird and began to claim my back was “so muscular and hot.” That was kind of odd. I said I had to get going and she tried hard to convince me to stay. I couldn’t wait to get home.

The Odd: I met a beautiful and booksmart Mexican lesbian from San Bernardino who was wanting to test out men… again (she had only one previous experience). We planned a day for her to come visit me and she literally wanted to have the “knock on the door, let’s just fuck” experience. I gave her a tour of the apartment and apparently that was too much dilly-dallying–she asked if we were going to “fuck or not?” Yes, ma’am. I got naked and she didn’t, as she wore leggings with a hole in the right spot. She was submissive, making me do all the work, but luckily, she did give some signs of life with her moans, a clue that things were going somewhat right (as far as I could tell for a lesbian). When it was done, she kissed me goodbye and said “thank you for giving me faith in men.” I never heard from her again.

Over the years, I’ve learned how to spot and avoid the bad and unneeded odd eggs. Nothing’s full proof, though. This summer, I kept on coming across a profile of a woman who by all appearances and words, seemed quite quaint. Definitely cute and smart, but I was hesitant to contact her because I thought she would be too straight-laced and boring of a person. Still, she was online at the same time I was once and our chat went well. After we met, it was obvious that I was colored a creamy white vanilla compared to her. I’ve never met someone so out-of-control hyper and wild than her. It was a mix of crazy good, dramatic bad and odd behavior.

Care to chat? Leave a comment below and follow me on Twitter at @Arrow405

Image from Remko van Dokkum.

  • noob

    My question is how do you get these women back to their places so fast? In my online dating experiences, it usually takes a few dates. Do you use C&F?

  • Arrow

    Hi noob.

    I think it comes down to trust, carrying a relaxed demeanor and carrying no expectations. To a lot of people, meeting someone from online is “weird” and “new.” The more low key and chill you act, perhaps the more comfortable your date might be during your time together.

    If you approach the situation like you already know each other in real life, it might feel like you’re too into it, or a bit too excited, scaring her off at first.

    Also, before the first date, e-mails and conversations have already been, let’s say, somewhat in depth, or at least very candid.

    Of course, every woman and situation will be different.

    So now it’s my turn to question you. What is C&F?