Author: Anne Dawson

Dating Dilemma #3: The first date

So you’ve gotten past texting and you’ve wrapped your head around the concept of talking to and even seeing more than one man at a time, but now you actually have a date. Awesome and terrifying in equal measure, simultaneously. Perfect, you are right on schedule. Meeting up for the first time should be fun and flirty, fraught with anticipation and excitement; however, more often than not it feels more like a job interview. There are questions about where to meet, (definitely a public place, don’t have anyone pick you up at your home until you feel some trust has been established); Is he going to look like his picture? Will I find him attractive? Will his voice drive me crazy? And the list is endless. I suppose it all depends whether or not you are a worrier.

Try and relax. First dates should be fun. As a general rule, men expect to pay on the first date, but if you feel strongly about it, you can go Dutch. For me first dates are practice for second dates. While awkward, try to see it as an opportunity to get out and talk to someone new. I often keep first dates short, something like coffee, a drink, or dessert; however, it really just depends on the person. I think it’s important for you to have a sense of what’s important to you on a first date and stay true to it. Here are some of my rules:

1. When possible, I like to talk on the phone before a first date. It makes me feel like I know the person better. If the phone doesn’t seem agreeable until after a meeting, I try to schedule something shorter, like coffee, in case there is no spark. I usually try to meet during the day also so that I don’t need a babysitter (Usually I can organize a playdate). If we did manage to talk on the phone, I’m more inclined to be willing to get a babysitter and go out for a full meal. Usually I let the man pick the place for a first date.

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Dating Dilemma #2: How Many is Too Many?

So last time we talked about the importance of writing and the dilemma of remaining pen pals for too long. Remember, writing is not dating. Last time I checked, you can’t hug a computer. So let’s assume you are successful at getting past the pen pal stage, now you have the dilemma: how many men can/ should I talk to at one time? I don’t really have an answer for this because it’s different for every person, but here’s what I know: online dating is a feast or famine situation. I have never been able to talk to one person at a time. I am usually messaging more than one man and I find myself going out on casual dates with more than one person hoping that someone special breaks free from the pack.

All of this is supposed to happen naturally and it’s supposed to be fun, but somewhere along the way it feels a lot like juggling fireballs. I took juggling once for a theatre class and it wasn’t fun then, so why would I want to make it a central part of my life? I wouldn’t, but then I never anticipated that I would be partaking in the world of online dating.

Some people really do try to only talk to one person at a time, but I don’t know how they manage this, so here is what works in my world. Remember though that I have a pretty liberal moral compass. I will text and talk to several men at one time. I will go on first dates with several men without being exclusive, and I might even kiss more than one man (we’ll get into that next week when we talk about first dates), but if I decide to get physical (hey, we all have needs), I try to limit this to one person; however, sometimes even that is tricky. Hey, things happen. But this is where it gets tricky for me. I will not have a parade of men in my home, that is a personal choice because I have young children. I am fine with them knowing that I date, but I’m not okay with them knowing all that dating might entail until I actually have a boyfriend that will stick around for a while.

So that brings me back to the dilemma: How many is too many? At the moment I’m talking to seven men. I’ve met four of them, been physical with one and I’m not really sure that any of them will turn into a relationship, so I’m still on the prowl. My ultimate rule is that if I start to feel like it’s a circus then I need to slow down. I should mention that my kids are with their dad at the moment. The other thing that really works for me is I try to be honest. I don’t pretend that I’m a girlfriend if I’m not. I won’t dodge a direct question, and I function under the assumption that any man I’m seeing is also seeing other people until we have the talk. Young people seem to understand the rules of dating a little more instinctively, but for me there was a huge learning curve.

Dating in your 40’s and beyond requires all of us to make certain assumptions:

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Dicey Decisions

I walked into the dietician’s office and slumped down in a chair. I had brought a notebook and pen, but I couldn’t bring myself to pull it out of my bag. “What can I do for you today?” she asked me.

I sighed, took a deep breath and searched for words. ‘What could she do for me?’ I didn’t even know where to start. I took another deep breath and then simply said, “I just need you to tell me what to eat.”

She looked at me with kind eyes, but she did not spring into action to give me a menu. She didn’t even ask me if there were any foods that I didn’t like or that I was allergic to. I was puzzled, but what started out as me trying to find an easy solution to dieting, turned into a conversation about the need for me to take control of my life, and ended with her telling me that it sounded like I was suffering from decision fatigue.

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The Not New Years Resolution

So, the elves have returned to Santa in the North Pole, the decorations are still up, but at this point they are taunting me because it is time to return to real life and get out of holiday mode, and I’m afraid to stand on the scale because my workout and healthy eating regime has been on vacation for a bit too long. Sound familiar? It’s the post-holiday blahs. It doesn’t help that it is also freezing out because winter decided to arrive after all.

The New Year’s Resolution is a way that many people combat post-holiday blahs. It’s a way to look at things with a fresh perspective, set goals, get inspired, or maybe it’s just a way to set yourself up for failure. I’m not a fan of the New Year’s Resolution because by February I feel like I need a do over. Like many of you, though, it does seem like a good time to set a goal, it’s the sticking to it that I need to work on. Take the gym for instance: In January memberships are up, classes are full, the locker room is overflowing, and the determination in the weight room is palpable, by March, not so much. So, how are your resolutions going to be different? For me it helps to call them goals and not resolutions. I’m not sure why the pressure of a resolution seems greater to me, but it does. Goals are something that I think people should always have. Big goals, small goals, even a daily goal can be helpful.

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Dating Dilemmas #1: When did dating become about being pen pals?

This will be a series of short articles where I will share my dating dilemmas with you. I am certainly open to hearing your stories too. I will provide a private way for you to share some of the doosies and then I will incorporate them into future dating articles. This is a place where I will change names and protect your identity too. So, game on. Dating websites, look out, here comes Anne.


Honestly, what am I supposed to do with this? What if I was feeling naughty? Am I supposed to tell a complete stranger? If I was willing to engage in such conversation when I don’t even know a guy’s real name, is this the kind of person he really wants to meet anyway? And if he does, then do I want to meet him? Is he too cheap to pay for a late night phone sex session? Messages like this confuse me. I understand that engaging in online dating means that one has to type before talking. I’m not sure when the phone became intrusive and too intimate, but here we are: welcome to the world of online dating.

Some pen pal pet peeves:

1. If the culture is going to be about writing, then learn to write. Proofread people. Seriously, I find myself desperately wanting to inject grammar and spelling lessons into online profiles. I know this sounds a little harsh, but most of us have been to high school and I know for a fact that they cover the difference between to, too, and two; your and you’re; quiet and quite, and the list goes on. When in doubt, have a friend read your profile so that you’re presenting the best written version of yourself. Maybe it shouldn’t matter, or maybe it should matter more than it does, but I don’t want to miss out on Mr. Wonderful because I misspelled that I have a college degree. Apparently, there are many really smart people attending collage these days. I know because they tell me so in their profiles.

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Desperate Dieting Doesn’t Work

This is not an endorsement for any one diet program, instead it is about my journey to lose ten pounds that became thirty pounds and could easily have become fifty or more. After I had my children, I never could get back to my goal weight, I was always about ten pounds away, and that went on for a decade until my life style changed and I wasn’t exercising as much and within a year I went from ten pounds to lose to over thirty. I would make some progress, but something always got in the way. I’m sure this sounds familiar to some of you. I’m not proud to admit it, but I fell for the sales pitch for supplements and quick fixes, I counted calories, and desperately tried to outrun a bad diet. Nothing worked.

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Calling all Heroes and Villains

All the world’s a stage,

And all the men and women merely players;

They have their exits and their entrances, (II, vii)

Shakespeare’s speech, from As You Like It is about the stages of life; however, I want to apply the words in a different way. Imagine if you will that your life is a play, and the people in your life are the men and women that have their entrances and exits in your story. Some of them will be your principal characters with long running contracts; others will have cameo appearances; and still others will have short term contracts, maybe just making an appearance for a season or so. The fact is that your life is a story and as such, it contains heroes and villains.

As I ponder Shakespeare and the roles that I play in my life: mother, daughter, sister, friend, partner, teacher, I realize that my roles evolve as life evolves. While I consider myself to be a thoughtful, caring and compassionate person, one who values honesty and empathy, it occurs to me that I am both a hero and a villain as I appear in the life story of others.

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Owning our position: The role of positionality

Politics aside, I feel the polarized nature of the country right now. My vantage point is one of visitor in a strange land even though I’ve resided in the United States for more than twenty years. Despite my long run, I cannot claim to be an American as I am still a transplant from Canada. Perhaps it is my position as a woman over 40, a mother, a Canadian, or a single parent that gives me my unique vantage point, but following the current election the tension feels almost palpable to me. That said, I am not taking a political stance, but instead I think it’s important to note that our thoughts and feelings about politics or religion or anything else is rooted in the position that we hold in society and the roles that we play.

What is positionality?

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Dodging the Gym via the Gym Bag

I made a new year’s resolution once that I would start going to the gym, so I visited a few gyms and decided that I would buy a treadmill instead. After the treadmill became a gathering place for piles of papers, boxes, and books, I decided that maybe I would give the gym another try, and so there became the issue of the gym bag. How big should the bag be? What needs to be in there? What’s up with these women (whom I envy, by the way), that come to the gym with a rolling suitcase? What do they keep in there? For two years I used the elusive gym bag as my excuse for not going to the gym. It was too heavy, or I didn’t know how the lockers would work, it was too expensive to buy duplicate beauty products. All excuses and all ridiculous, but obviously fitness was just a passing fancy for me. I didn’t really want to go to the gym because it isn’t just an hour of working out, it’s time to get there, and time to change, and time to shower afterwards, and figuring out how to fit everything I needed in a gym bag, so that I could seamlessly return to real life seemed impossible. I quickly got overwhelmed and decided that the gym wasn’t for me…and then I turned 40.

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