Dating Advice from the Masses

I met my ex husband Kyle in 1998. My dating experience prior to that fateful evening included:

– A 17 year old boy (my blind date) putting his hand on my 15 year old thigh and freaking me the hell out at the movie theater while we watched Aladdin with his friend and my friend.

– My first kiss and ensuing sort-of relationship with an anarchist I worked with when I was 17. To this day I don’t get why I hung out with him; I didn’t even really like him.

– A short but sweet romance with an older boy (meaning a senior) when I was a junior. I wrote him actual letters with pen and paper after he went to college because I had yet to open an email account. No one had, it was like 1993.

– A handful of frat-boy, short-term boyfriends in college, and a few more kissed who never reached boyfriend status. We didn’t go on dates, we met up at one of the small bars nearby or planned to be at the same party at the same time. Très romantique. My longest relationship prior to meeting Kyle was 3 months.

The last time I was single, as previously mentioned, I didn’t have a cell phone, the creator of Facebook was only 14 years old and no one could Google me to try to find out my past (a quick look now shows some references to my paid and volunteer work and my non-stellar Warrior Dash results).

What does all this mean? I’m almost surely destined to be a hot mess if and when I start dating again. But I’m getting advice – wanted or not – from friends and articles so that I’m slightly less predisposed to disaster when that first date comes around.


This 4th of July I spent with my sister and her husband since my kids were with their dad. After two very enjoyable bottles of wine the conversation turned to dating.

My sister is a beautiful woman, the kind who has been dating almost constantly since she was 13 years old. She met boyfriends at school, on dating websites, after friends set her up. She got asked out everywhere she went, whether she was attached at the time or not.

Her advice to me was to wait at least a year before trying to navigate the world of dating. “You need to figure out what you want and where you’re going,” she cautioned. But her husband, who had been previously married and divorced, said, “Well, a year is a long time, and she’s already been living apart from Kyle for a year, so isn’t that kind of the same thing?”  I also added that since I’m closer to 40 than to 30 now, I feel like I have some sort of deadline for being dateable in the online world – I’m already over the age range so many guys put on their searches of 25-35 years old.  We also discussed whether I should do some test dates with people I wasn’t necessarily interested in, just to get experience so that I’d be ready for when I met someone I truly liked. But that seems a little like test driving a car you have no intention of buying – “Hey, thanks for the ride and your great pitch, but I’m not really serious about you. Later!” I thought about how I’d feel if I could tell I was someone’s test date. Around this time I vowed to never date anyone for the rest of my life.

My resolve lasted about four days, around the time my good friend Hildy started up at Match again. Her stories haven’t resulted in true love yet, but boy are they entertaining. And they all contain a bit of two things at the beginning – hope and excitement. Who can’t use a little hope and excitement?

So I’m back to thinking about dating again and more advice keeps coming at me on a daily basis. Friends, coworkers, Twitter accounts I follow, dating advice blogs to which I sort of on purpose subscribed, all of it. But I’m no less confused.

– Megan said she never gave her phone number to prospectives, not until after the first date; Hildy likes to talk to guys before agreeing to meet them.

– Megan’s husband Raymond said I should get some experience dating anyone, just jump in; Megan says to wait (but wait for what, I ask??).

– Megan said to never let a man pay for a first date; Raymond said the man should always pay. Online articles mostly agree with Raymond.

– Another pal, Kami, said when online dating she never went out with someone who made the first move, only guys SHE contacted; Hildy is okay meeting with a guy who contacts her if she thinks they’ll connect.

– Kami said she dated not just for love connections, but just to meet new people; Megan said it may not be fair to the men I go out with for me to be looking for merely a friend if they are looking for love.

Is texting a new date okay? Are phone calls outdated? At what point would you friend someone on Facebook? What would I do if someone tried to kiss me and my first instinct was to duck and take cover? The prospect of a new first kiss after this long kind of makes me want to run away. Am I supposed to tell a guy I want to see him again after a date? How much is it going to sting the first time (of probably many times) I’m rejected or ignored? What am I supposed to drink if a guy wants to meet for coffee if I don’t drink coffee? How do I fill out the Body Type portion of an online dating questionnaire if I’m smaller than the average American woman but not currently athletic and toned?

It’s mind-boggling. I don’t feel quite ready to do online dating yet because I worry about looking like an industrial-sized can of expired chicken noodle soup next to shelves full of fresher, more attractive and more flavorful options in smaller packages. Maybe that’s what my sister means when she says I need to take some time? You think?

For now I’m practicing with online dating by having a fake Match profile – none of the details on it are true and since I don’t pay I can’t contact any members, anyway, but I amuse myself a few nights a week by browsing through the 5 or 6 men who say they’d date a woman my age who has children. And I’m guessing at least half of those profiles are as fake as mine.

Do you have any good dating advice for me? Any links to some great dating stories, good or frightful?

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5 thoughts on “Dating Advice from the Masses

  1. Pingback: I Decided I Wasn’t Ready to Date, So Now I Have a Date | A State of Motion

  2. Pingback: First Date – The Good and the Bad | A State of Motion

  3. Pingback: Lessons About Texting While Dating – Date #2 | A State of Motion

  4. Never request them on Facebook first. You can accept theirs… maybe. Probably don’t though.
    Texting before a date rule: Less is more. Keep texts under 8 words at all times.

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