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My Adventures in Dating

Updated on November 5, 2014

Dating Tips

Be assertive: Ask the person out on a date, if that's what you want. It doesn't matter what gender you are, modern society has thrown out all those rules. You have to be clear about what you want and to know how to get it.

I had a guy once say to me, "Well, if you ever feel like going to the movies or something, I'm always around..." Being that passive was a total turn off. Did he want to go to the movies with me or would he just be doing me a favor by taking me? He left it all in my hands and didn't make me feel like he necessarily wanted me.

Say what you want and you're more likely to get it!

Suddenly Single

Dating is terrifying! It's like walking into a jungle, with no map, no guide, completely unarmed, and sometimes without even a bottle of water. Finding myself single, over 30--with a small child!--after an 11 year relationship, I realized I was virtually clueless about dating. I couldn't rely on my past experience as a teenager, or what Seinfeld had taught me, to get me back into the scene. It's a completely different ballgame, factoring in my age and the contemporary over-use of technology.

When I first left my husband, I was not in the emotional state to jump into another relationship. I knew my priorities were taking care of my legal battle and ensuring the safety and happiness of my son. But, a woman has needs, and I craved some positive male attention. Anything I may have indulged in at the time was purely recreational and meaningless. The thrill of those encounters soon wore off, however, and I began to grow lonely for a deeper connection.

Dating Tips

Don't be pushy: OK, great, you feel a connection to someone and you're eager to go further. But, hold on. Take a breath. Give it a moment. You might be jumping the gun, getting a high off the endorphins your brain released during your first encounter without properly judging your date's mood. Wait until tomorrow to ask for the second meeting.

I hate it when guys talk about a future together that may not actually happen. "When you meet my friends..." or "You'll understand when you see my apartment..." or "My mom's gonna love you!" Slow down, cowboy! How about focusing on the now, impressing me enough to get a second date before you pick out matching monogram hand towels?

The Search Begins

I began to look for a man I could actually go on a date with. I wanted interesting conversation, emotional stability and the potential for a healthy physical relationship. There did not seem to be any candidates. I flirted with every good-looking male customer I served, and asked every friend I had to hook me up. Every man in lower Westchester County, NY, between the ages of 30-45 is either married, gay or both. What was I to do?

I had decided to move out to Pennsylvania in an attempt to "start over" with my son, hoping it would also bring me new opportunities in finding a man. But I went from my native world of an upbeat urban environment to a small sleepy town east of nowhere. I met no one. Everyone I worked with was too too young, and I had no social life outside of work. It was incredibly discouraging. I had to explore other options.

Date Online

Have you ever or would you ever try an online dating service?

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The Figures

Meeting Place
Divorce Rates
5.9% online daters
through friends
7.7% offline daters
according to a Daily News article, June 2013

Going Online

I was always weary of meeting someone online. Ever since the invention of the internet, we've all heard those horror stories of creepy old men in chat rooms luring young teenagers into their homes or those serial stalkers who put up a great front but end up invading your life. Why would I want to set myself up for that? I already have a crazy ex-husband, would I be able to filter out the psycho factor in my choices of a potential mate enough through the internet? But, everyone I talked to seemed to know someone who met their husband/wife on a dating website.

So...why not?

(Disclaimer: I am not here to criticise any particular site or discourage future users. This is only an account of my particular experience and not a judgement of the sites' success rates.)

My first try was on ( The hardest part was writing about my life in a way that was appealing to the specific mate I hoped to attract. I must admit, I was not particularly happy with my life at the moment and had trouble being positive about it. I did enjoy looking the pictures of the men the site matched me with--shopping for men, I called it. I "winked" at all the best looking ones, but they never responded.

Anyone I communicated with really didn't seem to connect with me. All the intellectual men were in their 50's and 60's. Now, I don't have anything against dating older men, but where would it lead? I'm in my 30's with a young kid and they've already been there, done that. The younger men had more future potential, but were all sporty, outdoorsy types. I like to read and write and do research for fun. I'm a bookworm, a sci fi nerd. My friends would joke that I'd only marry a guy (next time!) if he watched Futurama. These guys all went rock climbing and kayaking and played football. I don't even understand football. There were no connections on for me in Pennsylvania.

Back in New York

Life in PA didn't work out for many reasons, and I was happy about my move back home to NY. I kept my subscription to Match until it expired, hoping to connect with some decent guys. No such luck! A lot of men would stop communicating with me once they found out what I do for a living. They were all professionals, mostly living in New York City and traveling a lot. I work retail and have full custody of a small child. I'm not as financially or as socially mobile as they are.

I did get in touch with some more down-to-earth kind of guys, but none has any promise. One was just needy and weird and I couldn't figure out what he wanted from me. Another was super cute and very sweet and had two small kids and seemed to have some things in common with me. But he was rather emotionally immature and liked his toys a little too much. Cars, motorcycles, video games and guns. No thanks!

The last guy I communicated with through Match seemed perfect! He was beautiful: over 6 feet, muscular, originally from Africa, complete with the exotic accent. He was a high school History teacher and musician. Out first conversation was about which was better, Star Trek or Star Wars? (I'm an equal-opportunity nerd, anything about space is awesome!) We talked every day for three months. But we never met. I was subtle about it at first, but I eventually outright told him we should get together and he never seemed to really want to. Why go on a dating website if you have no desire to actually date?

Dating Tips

Step outside the box: Preconceived notions of who you should date and how a date should go will only hold you back. It's great if you have a type, specific things you're attracted to in a partner. Limiting yourself to only those factors, will continually disappointed you.

I have a type: gorgeous a--holes. When I decided to look for a serious relationship, I realised those things that initially attract me won't keep me around in the long run. Putting superficiality aside--yes, there has to be some physical attraction!--I was able to look for more substance in a man's personality.

And, of course, we all want to be doing things we're interested in when out on a date, but it can't be confined to only certain activities. You have to open yourself up to new experiences and not expect a night out to follow a specific formula. I like to have things planned and know what to expect from my evenings. I usually even plan my outfit up to a week in advance, so knowing where I'm going definitely helps. But, dating someone who likes to "wing it" has given me some fantastic evenings that I wouldn't normally have experienced. Try something new! It might be fun!

Cupid's Arrows

So, still no dates! Within a week, I had three different friends suggest OKCupid ( Couldn't hurt, right? I actually had fun doing my profile on this website. The self-summary always takes some time and a lot of thought, but I was in a better place in my life so I really put some effort into it. Also, OKC asks like a billion personality questions with some sort of mathematical algorithm to best match you with a potential mate. Before I new it, I was getting tons of messages from guys. Granted, most of them were lame--"Hello"--with no potential for a conversation, and many were just telling me how beautiful I am. Yeah, every woman loves to have her vanity appealed to, but I know I posted my best photos and what could I possibly respond to that besides "thanks"?

I had to filter through the messages until I found a few guys worth talking to. I had hoped, at first, that a man with children and previous long-term relationship experience would be the best match for me. Someone who knew what I was going through with the divorce and being a single parent. I soon learned that they carried as much, if not more, baggage than I do! I wanted someone with LESS drama and chaos in their lives. So none of those guys worked out.

I was soon keeping up a steady discourse with three different guys. And, I was ready to get out there to date!

Dating Tips

Say "Yes" to every date: I've heard this mantra from so many women who are on dating sites. Of course, trust your gut and if there's anything you feel shady about, don't go. But,if there's a positive connection, go for it!

There's no limit or preset amount of time between first contact and meeting. Do what's comfortable for you. I liked to get to know someone through emails and texts and phone conversations for a quite a while before I was ready to meet anyone. But, if you'd rather experience the dynamic in person as soon as you feel any sort of connection, then do it.

The only way to know if the person is right for you is to meet them face-to-face.

The Dates

Finally, someone asked me out! We were to meet for drinks at a bar in my neighborhood, which was easy access and an easy escape for me. I wasn't 100% attracted to this guy, either physically or intellectually, but he was very sweet, and I was trying to go at this with an open mind. He was kind of boring and I had hoped a few drinks would liven him up. He told lots of stories that went nowhere and did not know how to respond to anything I said. We didn't have much in common, in fact, I had a hard time finding out what his interests were. He doesn't watch tv, but picked up an episode of Doctor Who at my suggestion. When I asked his thoughts on it, he said he didn't understand the show, but couldn't give me any details so I could clarify anything. I told him how I liked books, I have a BA in Literature. He revealed that he collects art-related books because he only likes to look at the pictures, but couldn't tell me much about the artwork or artists he likes. Though he was very touchy-feely, he never made a move. I left after our third drink. It was 11:30 pm. Lame.

The next guy I went out with definitely had more personality, but the date was so much worse! He turned out to be needy and pushy and crazy. He called me about a dozen times that day, totally freaking out about getting to the restaurant, since he's not from the area, and was late getting there anyway. He was way shorter than I expected, and way creepier in person. It didn't help that I was wearing five-inch-platform sandals and looked as hot as I could while still being casual. Ok, ok, he thinks I'm hot, fine, but the dude didn't have to stare at me all through dinner. The conversation was terrible, he talked way too much about his ex, but hardly listened to what I had to say about mine. He kept telling me that I'm going to be alright in life, even though I was explaining how I've gotten to the point where I am fine. Then he says he's been to Federal prison. Done, check please!

Except, that it was only 9pm. Outside the restaurant, he says, "this date isn't over yet!" I wanted to run away, but felt bad for him. So we went for a walk, in the direction of my home, so I'd have a quick out. We ran out of things to talk about and he says needs to know something right away. "How attracted to me are you?" he asks. What? Who even asks such a thing? I was stunned. No, I was not physically or mentally into him, but I had intended to let him down gently, without hurting his feelings. But, he kept pushing it. "You were disappointed when we met, I could see it in your eyes." What? Now he was speaking for me. I felt so uncomfortable, but I still wanted to ease out of it. I tried to explain how sometimes attraction can grow as you get to know someone.

But he still wouldn't let it go, and i had to end this! I offered to walk him to the train station so he could get home. He was surprised I wanted to end the night, even though I kept saying how awkward and uncomfortable he was making me. I tried to take some control and make a dignified exit. Then I fell. Uneven sidewalk, 5 inch heels. Right down, tearing a hole in my favorite jeans, and scraping my knee! He didn't even help me up, just kept talking about my lack of attraction to him. So I gave him directions to the train and started to walk away home. The jerk had the nerve to ask for a kiss goodnight! Way to not read the vibe, dude.

Dating Tips

Learn to let go, and move on: Not just from a particularly bad date, but from people in general. If someone isn't right for you, it's ok to end the relationship, at any stage. If the first date is awful, you don't have to continue communication. If you do start seeing someone and it goes south, be honest with yourself and that person when you realize you're unhappy. It does no one any good to stay with someone if it only causes you, or both of you, more stress than happiness.

But, you also have to learn to be ok with rejection. You might be excited after a first date with someone, but he never calls you again. Not everyone is going to love you instantly, but that isn't necessarily a reflection on who you are. Sometimes the chemistry just doesn't mix. Sometimes things go badly when you are more deeply involved with someone, but it's not the end of the world if the relationship ends. In order to find happiness with yourself, and with a new relationship, you have to let go of the old one. Don't let your feelings, good or bad, for your ex ruin the chance at finding someone new.

There will be a person out there who "gets you," who wants the same things and brings happiness into your life. Let the bad ones go, and be ready to embrace the good when you find it.

A New Hope

Feeling discouraged, it would have been easy to give up and get off the dating sites right then. I was also on Plenty of Fish (, but had little hope from that site. It seems to be more of a casual atmosphere, not really for people looking for a long term relationship. The profiles aren't very extensive and I'm not sure anyone actually reads them. I had to delete the POF app from my phone because I was tired of the daily barrage of "you're hot" messages.

I didn't give up, though, since there was one last chance. Almost from the beginning of my time on OKC, I was chatting with this one guy, a computer programmer in NYC. The travel time into the city was a deterrent, at first, but I really liked talking to him. He's smart and nerdy and really laid back, with a lot of similar interests. We even have the same favorite band. When does that ever happen? Eventually, we decided to go on a date together. It took an entire month for our schedules to coincide and actually get to see each other, but it was definitely worth the wait.

I remember being so nervous on the train, going into the city on my own. I get lost really easily and can not navigate the city streets, so the anxiety was high from having to meet someone new and being out of my element. But, he is a gentleman and met me at Grand Central Station. I was blown away by how sweet he really is. After dealing with a bunch of jerks for so long, it was such a relief to meet an actual nice guy! He's a lot of fun, patient, and understanding and as nerdy as I am. There was little doubt we would have a second date!

We've seen each other now every weekend since we met. It's only been a few months, but we are both off the dating sites. Sometimes, I wish I had met him sooner, but I think we both needed our respective negative experiences in order to appreciate the good we have with each other. I'm not at all sure where this might be going with my sweet nerdy metal head, but that's cool. I'm enjoying the ride.

The sites

FREE--limited access Paid subscription--Full access, including STIR events
decent profile set up. good of looking for long term, users seem to be serious minded about relationships
OK Cupid (OKC)
good profile, tons of personality questions. very open-minded and popular with the gay community. can choose to match for anything from friendship to marraige.
Plenty of Fish
minimal profile. users seem to be looking for casual hook-ups.
Disclaimer: This is not an advertisment or critique, but a summary based on my experiences


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    • Gypsy Willow profile image

      Gypsy Willow 

      5 years ago from Lake Tahoe Nevada USA , Wales UK and Taupo New Zealand

      I enjoyed reading about your experiences with on line dating. Hope your current contact works out for you long term. Good luck.

    • okanagangurl profile image


      5 years ago from Canada

      I couldn't stop reading your article. Great piece!

    • Ingenira profile image


      5 years ago

      That was fun reading about your dating adventure. :)


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