Real Dating Advice


Concerned as I was by a friend’s comment that I seem to be writing a dating blog in which there is no dating going on, I reached out to my very wise, very insightful fellow blogger, Ann St. Vincent ( for advice. I thought her response to my query worth sharing with you.

Amy, my dear,

You can spend hours, if not days, trolling blogs and websites extolling all kinds of advice on how to date, how men are douchebags and women are hard to please.

It’s overwhelming, frankly, and not very helpful.

I never particularly thought of myself as adventurous or brave…but now being on the other side of a marital split, people seem compelled to:

a) tell me the state of their own marriage,

b) tell me how they live vicariously through me and my sexy adventures,

and c) tell me I’m super brave, and they are wowed by my ability to make a tough decision and move on without a lot of the baggage that comes with it.

I never particularly thought about myself this way. But I realized I do have a habit of breaking things down, figuring out the root cause of my issues, coming up with a plan, and then executing the plan. It doesn’t always work, but then I repeat the process.

When you asked me to write this guest blog, I really had to think about the key things I’ve learned that in my opinion, have given me the cohones to start dating and move toward the life I’ve always wanted.
This first draft of this was almost 2,000 words and outlined a whole number of things which I think leads to dating success. I think you may have found it a bit overwhelming. But then I realized my philosophy all boils down to one key principle:


Mock not. It’s true. IMG_1389
I will break it down for you.

Step One: In order to date, you first have to think yourself worthy. We spend an inordinate amount of time worrying about whether we are too fat, not muscular enough, if our nails look pretty, if our hair is right, if we are too old, etcetera. I know you understand this, Amy, given your theatre background.
Literally. Think of all the industries that would instantly go out of business if we decided we were happy with our bodies and ourselves. So…if you can learn to not take any of that shit too seriously, you are off to a very good start.

Case in point. I do not have a small butt, even for a 5’10” woman. I’m not too pleased about this fact, and I try to eat well and exercise, but at the end of the day, I had to realize that for every large ass, there are plenty of men who will appreciate it. Some have even worshipped it (their words).
So? I try not to take my ass seriously anymore. Confidence is far more important.

Step Two: When it comes to deciding whether others are worthy of dating us, we also spend a crazy amount of time obsessing. What kind of job do they have, are they “right” for us, do they want / not want children, how fit, how tall, how smart, how rich.

It’s no wonder women complain that there are no men out there (I actually wrote a whole post on this after getting tired of all the blogs with this complaint). It makes sense to do some thinking about what you need (which is very different from what you want. Know the difference).

Tip: if your list fills a page, it’s too long. Think about the top few things. No more than that.
Here are mine:

1. Someone whose intellect I respect

2. Must be kind

3. Need to keenly enjoy affection and sex

4. They have to have something they are passionate about (work or hobby)

5. Good communicator: mean what they say, say what they mean Oh, and if they want their own biological child, or if they are married / in a relationship, it’s a non-starter. I don’t even bother…because it will just end badly.

Okay, but back to the fun stuff. Once you figure out the few things that are your non-negotiables, everyone else is fair game!! I went on a date with a crazy Russian-Persian dude that wastotally not what I thought my type would be. We had a great time. I went on a date with a plumber who turned out to be the best-dressed of any man I’ve gone out with yet.

Now, neither of these worked out in the long run, but since I don’t take myself that seriously, I walked away unscathed.

So try it.
What’s the worst thing that can happen?

Okay…don’t answer that.

At the very least, you have stories with which to regale your friends.

This also extends to women who have complicated rules for whether they respond to a guy. One girlfriend once complained she wasn’t going out on any dates. Turns out she had all these rules about type (see above) and also about what a guy had to say online if she was going to respond to them. Once she dumped that rule, presto – dates!

Step Three: Be a fun date. Remember dating? It’s supposed to be fun. When I became single, I was horrified to realize a “dating coach” is an actual profession. Sweet God. Is this what it’s come to?
Don’t ever do that, Amy. Call me first!!

I decided right then and there to just have some fun. You have to be willing to put yourself out there, reach out to people you are interested in, talk to cops who pull you over for speeding tickets (yup, I did that), and have enough self-confidence to roll with it when you don’t hear back from someone, or they don’t respond in kind.

People can be assholes. Take that as fact and then you will be delighted when you hear back, or when someone is normal and decent and interested. Just be yourself. There’s a expression I love: “be yourself…just be your bestself”.

The reality is if you try to be anyone else, you’re going to fail. It’s like interviewing for jobs…you should be interviewing them as much as they are interviewing you. If they don’t like you for who you are, then you shouldn’t be dating them anyway.

This is a tough one. Of course we all want to be wanted. Rejection, even from someone you didn’t particularly want anyway, still stings. But, if you have fun with it, always have a few people you are talking to, realize they are doing the same thing? It will serve you well.

You always have the option of focussing on one person, it might make it all a bit better.
Final Step…(Optional): Continue to write your blog so you have a place to put all your horrific stories of bad and weird dates. It will amuse your married friends to no end.

If you follow this advice, you are guaranteed to have a whole bunch of great stories.
Don’t take yourself or dating too seriously, and you will relearn how fun it can be.

Who knows, you might even find happiness somewhere along the way.

yours very truly,



16 thoughts on “Real Dating Advice

  1. Pingback: 50 Dates in 50 States Guest Blog | Real Dating Advice | ann st vincent

  2. Hi Ann (and Amy),

    I loved your post Ann. So true. Be yourself and don’t take it too seriously.

    I am in the middle of an online dating agency saga. After 3 months we still haven’t met so our relationship is more like a Yahoo Messenger Pen Pal experience. If we do ever meet face to face I will remember this post as it will probably be archived in the bowels of the British Museum by then.

    You selected a great guest Amy. Ralph xox ❤ ❤

  3. Excellent advice Ann, some of this was precisely what I needed to hear (all of it was good), and I’m sure that goes to say for many other people. Entering the dating arena for the first time in 14 was a bit scary for me, but I think my biggest obstacle has been my skepticism. It’s really just like you said though, “What’s the worst that can happen.” and it is REALLY important to not answer that for yourself, but to find out. I’m guessing many more times than not, things are just great and the “worst” things really do make for good stories.

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