The trouble with middle-aged dating

I’ve been grappling this week with how to approach the next installment of my singleness/dating project.

It’s time for me to come clean you see.

Since the beginning of this endeavour, I haven’t been completely forthright about my singleness status………per se.

There’s been someone in my life.

However, the relationship has been so casual and intermittent that I haven’t actually considered it to be a relationship. It’s been an FWB (friends with benefits) situation, if I can be so crass.

He’s someone I’ve known for years and there’s a close connection with friends – which is why it’s been tricky to navigate and define.

His best friend is married to my best friend.

You can’t get much closer than that. So the difficulty lies in the fact that if it doesn’t work out, we’ve messed things up for more than just ourselves.

I think everyone’s nervous about the outcome of this one………………….

As we’ve been ‘hanging out’ however, we’ve both realized that our feelings have grown maybe a bit beyond the FWB status.

And more recently, I’ve started bringing up thoughts about the future and what we’re both looking for. The trouble is that I seem to be a little clearer about what I want: a committed relationship, eventually leading to children and a family.

He, on the other hand, is not so clear and gets nervous when I bring up the topic. It’s not that he definitively doesn’t want children, he just can’t say that he definitively does. So where do we go from there? He knows what I want and respects that, but is afraid he may eventually disappoint me in that department and as I’ve said before, I’m not getting any younger.

With that information in hand, I set out on a mission to meet other people, which is where the last guy comes in……………….

And although I’d told dater No. 1 I was planning to meet other people, when he realized I was actually following through, he wasn’t so keen on the idea. It was easy for him to slip back in because the feelings and attraction were already established.

But the problem isn’t solved yet because life doesn’t always follow the script of our favourite rom-coms. In the movies, the guy finally realizes how stupid he’s been and wins back the leading lady, usually Jennifer Aniston, with some romantic gesture. The final scene is a mixture of kissing and crying and the assumption that everyone lives happily ever after.

In real life, there may be the same romantic finale, but then the story continues and it doesn’t always end with ‘happily ever after’.  Actually, more often than not, the two probably break up again a week later when they realize that nothing has actually changed from before and a real relationship is not about one superbly romantic moment after another.

So, the saga continues and so does the dilemma.

Dating at this age is a difficult process. On the one hand, you don’t want to go into a relationship pushing for holy matrimony and a bevy of bouncing babies. What guy is not going to run, as fast as he can, away from that girl? And rightly so; a relationship needs time to grow and develop and for feelings to emerge.

But on the other hand, time keeps ticking, relentlessly, away.

It’s a double-edged sword in which there’s no real ‘Winning’ as someone we all know and love would put it. Like life in general, dating is just a series of tricky choices in the hopes that you will eventually find the answer.

The Dating Project

Okay, so I’m not sure if any of you have noticed, but the tone of my blog has changed.

It started off a place to celebrate singleness.

My objective was not to whine and complain about the misery of being single or to lambaste prospective suitors after dates-gone-wrong. I wanted to be different; I wanted to be positive about singletude and say that it’s okay to be alone.

What’s changed though, is that when I started I wasn’t ready to be unalone (I know that’s not a word!) But now I am. Indeed I find myself wandering into the danger zone. So my posts can go one of two ways: here’s what happened on my last worst date or; I just wish I had someone to love and I’m so lonely.

I’m not comfortable with either option so it’s time, my faithful readers – all nine of you – for the evolution of the Singleness Project.

As with life, everything changes and evolves and so must this blog. I’m afraid I’ll have to proceed with a proper renaming to the Dating Project. Yes, that’s right my friends. I am now dating!

If all goes well my hopes are that it will further evolve into the Relationship Project, and finally, the Marriage Project.

I’m aware that it’s very 1962 to be a woman looking for marriage, but why is it such a terrible thing?  We are social animals who crave intimate connection with one another and despite the fact I didn’t have the best role models for marriage growing up, or maybe in spite of that fact, I long for a true partnership of my own. Someone to have my back, love me even when I’m acting like an ass, and think I’m cute when my hair’s frizzy and my butt looks big in those jeans!

That’s what it’s all about isn’t it?

I won’t bore you any longer with the philosophizing and get right on to the dating.

Today I went on a second date with an online match. It was probably one of the best second dates I’ve ever been on and I have to be careful saying this because he knows my blog address and has been reading every installment! Anyway, what made it great was that I felt so comfortable. We talked and laughed and both agreed on how inappropriate but funny it would be to call our kids Jamal and Shanniqua (he’s asian, I’m a white chick:). We didn’t talk about much, but talked about lots of things at the same time. I felt relaxed, he was sweet and kind and funny and surprisingly, seemed like he might be interested in a…………….dare I say it………………..relationship.

That’s my first installment of the Dating Project.

I will let you know how things go. I’ll try not to be malicious or unkind, too judgmental or critical. My intention is not to negate every suitor or critique every awkward moment. My hope is to truly Keep the Dream Alive.

I’m not an NHL player hoping to win the Stanley Cup or a mountain climber wishing to scale Kilimanjaro. My single, tiny, and solitary dream, is just to find someone to rub my back when it’s sore, tell me I’m good when I feel bad and share the toilet paper with...............

My new man

It’s true friends, I’ve found a new man!

His name is Frank and I met him in Victoria.

He’s committed, faithful and always there when I need a shoulder to lean on.

Frank is solid through and through. He offers support when I need it and is never judgmental. He’s happy and positive and always has a smile on his face. Frank is sturdy and strong; he let’s things roll over him and never gets flustered. When I’m upset he’s there to listen and be my friend and confidante.

Frank is my rock.

                                          Frank and I at the river.........................

                                         Talking about our future together........

                                  Him agreeing that he should do most of the household chores......

                                         A tender moment.

                                         Our first fight!

                We made up; he shed a few tears but agreed that I was right in the end.

Beautiful Victoria.........Part Deux

It seems I spoke too soon. The sun is out and shining and I'm heading out to soak in the glorious rays!

Sorry Victoria..........my judgement was too harsh.

Beautiful Victoria

I’ve chosen the greyest, rainiest part of the continent to enjoy for a few days over my March Break: Victoria, B.C.

Well, I’m actually here to visit an old friend who’s living with her boyfriend for a year while he completes his Master’s degree.

I’m also here just for a little retreat and because I’ve never been to Victoria before and always heard how beautiful it is and it’s true, it’s a lovely little city. But it literally has not stopped raining since I arrived four days ago.

The funny thing is people here seem oblivious to it.

While walking home from a hot yoga class with my friend last night – which by the way was terrible and I’ll never do again; the hot part was ridiculous, I hated it and left before the class was even finished – anyway while we were walking home, a pretty good rain set in. It was the kind of rain that people in Toronto would flip open their umbrellas for, run indoors for, but I followed my friend’s lead and she had almost no reaction. We both put up our hoodies, but that was about it. I guess you just have to get used to being wet around here.

I’ve also asked several people – servers, cashiers, another friend – if it’s always like this in Victoria and they’ve all given me vague looks and nodded saying, “Pretty much” as though they’re not really sure what I’m talking about.

Then, just as soon as I thought nobody else was even noticing the rain, the other day when it started coming down a little harder, I popped into a store and everyone was suddenly commenting: “It’s really coming down out there!”, or “Oh no, is it raining out there?”

Um, yeah, it’s raining out there.

Last night while my friend and I were sitting in her apartment, trying to come up with a plan for the next couple of days, she said: “Let’s check the weather forecast for tomorrow, maybe we can go for a bike ride!”

Even before the screen popped up, I knew what it was going to show, but she seemed somehow surprised.

“Oh no, it’s going to rain!” she said, disappointed.

                                        

 

Multi-task dating: An advice column question in the paper recently got me thinking about how much of a passive dater I’ve been throughout my dating career.

I’ve never been one to date around or date more than one guy at the same time. The idea has always made me feel a little uncomfortable like it’s a moral issue and dating more than one guy somehow makes me a bad person.

But I’ve been re-thinking this notion a bit lately, because, why not multi-task with dating as with everything else in life? I’ve also been inspired by my friend from my last post who is happily dating a couple of guys at once and I certainly don’t think poorly of her. In fact she’s a great person and I say good for her!

The question in the paper came from a young woman who’s been dating two guys but she doesn’t like playing the field; she’d prefer to settle down. She explained that one of the guys is kind and responsible but “kind of boring” while the other is fun and exciting but “kind of irresponsible”. The advice columnist told her exactly what I was thinking: She shouldn’t give up looking just because she’s getting tired of dating. She said she’ll know when she’s found the right person or when she’s found love because she won’t have to describe them as “kind of boring”. Maybe she needs to keep looking and dating around.

So why shouldn’t I date more than one person? In fact, that’s probably what I’ve been doing wrong all along. I can think of a few times when I’ve gotten into a relationship, fast and furiously, maybe more based on physical attraction, only to discover six months or a year in that the person is missing some key qualities that are important to me. 

On the other hand, I’m reading a book right now that makes the case for “settling for Mr. Good Enough”. The author, a 40-something woman who passed up many great but “kind of boring” guys in her 20s and 30s, now finds herself single and longing for a husband in her 40s. She wishes she could turn back time and give some of those kind-of-boring guys a chance.

How depressing. I say keep reaching for the stars, get to know lots of different people and keep your expectations realistic at least. Anyway, kind-of-boring can be kind-of-nice sometimes, at least it's better than kind-of-mean.

The dating game

I was chatting with a single friend today who’s dating two guys at the same time.

It’s not that she’s a big, two-timing  ‘ho or anything like that, she’s just trying to find the right person. After a run of online first dates where she said no, no, no with a capital “N” to each, she coincidentally met two ‘yes’s’ around the same time. She’s had about three dates with each even though she assumed she’d be able to scratch at least one by date #2. But that just wasn’t the case because she liked them both. This, if you’ve ever ventured into online dating, is something you don’t just toss away.

The most interesting aspect of the situation is that both guys have a totally different game. Dater No. 1 is cool and casual but continues to show interest with texts every few days and asking her for dates intermittently. Dater No. 2, on the other hand, is super keen and not afraid to show it.

My friend can’t figure out which approach, or which guy, she prefers.

There’s a fine line between keen and desperate and an equally fine line between laid back and non-committal. It depends on how adept each guy is at working his particular shtick.

Keen can be charming and endearing – it makes you feel good about yourself, attractive and wanted. It’s also a turn-on when a man has the courage and confidence to express how he feels, and it’s hot when a guy knows what he wants. But too eager, and especially too eager too soon, is not so cute. When a guy is all in before date No. 3 it just makes him seem insincere, and kinda creepy.

 In the same vein, laid back can be mysterious, challenging and exciting. It gives you time to figure out how you feel about them, the opportunity to get to know them more slowly over time and the space to continue to be your own person.  But if the pace doesn’t pick up after a certain number of dates the wishy-washy “Let’s see how things go” gets tired and loses its appeal.

My friend’s choice will eventually come down to how each relationship unfolds. If Mr. Keen turns into Mr. Overeager with no signs of relaxing into normalcy, he might be kicked to the curb. Conversely, if Mr. Cool doesn’t pick up his game after a certain number of dates, he could lose his chance at the final rose.

It may be in her best interest to start securing Dater No. 3…………..just in case.

Keep the dream alive

Today I found myself going over my list of 25 things that will make me a happier single, from one of my first posts: My List.

#19, Keep Dreaming and Don’t Give Up, jumped out at me.

You see my friends, keeping the dream alive is no easy feat.

I have gushed about all the glorious aspects of singlehood including free time, not having to worry about anyone else, eating grilled cheese sandwiches for dinner, free time, hanging out by yourself on a Friday night, and again, free time. But in all honesty, if I haven’t already given away my cover, I would like to find “the one” , get married, have a couple of cute kiddies and live happily ever after. Isn’t that really what everyone wants deep down? Maybe not, but I know there’s probably a good reason why people keep doing it over and over again.

So it can be frustrating when life doesn’t seem to be unfolding that way.

I watch my friends carry on with their husbands,  toddlers, preschoolers and beyond and sometimes I wonder if there’s something I’ve done wrong along the way? Maybe I missed my chance at love and happiness and don’t even know it. I know I’ve made mistakes but does that mean, I wonder, that my chances are all used up?

 Sometimes it’s hard not to believe that, but for the rest of the time I try to keep the dream alive.

A good friend reminded me a few months ago when I was in the depths of self-pity over my most recent break-up, that I should never stop dreaming. In an effort to be practical about my situation, I had admitted that I thought I may never find the right person and could spend the rest of my life alone.

“Well with that attitude you will!” she admonished.

I told her I was just trying to be realistic and prepare myself for the inevitable to which she responded: “Don’t ever stop dreaming!”

Thanks for that Lor. This one’s for you!

The sentiment stuck and it’s been floating around in my head ever since. Replaying those words has gotten me through some difficult patches of late and also helped me to see more clearly what could be a bright, sunny spot in my future.

As someone who I'm sure was important once said: If we don’t have our dreams, what else is there?

Here's the skinny

I can’t believe it!

A mere two months after I finally gave in to the trend and bought myself a pair of skinny jeans – jeggings in fact – the look is kicking the bucket.

Long Live the Flared Leg- Toronto Star

Now I’m quite aware that the topic of skinny jeans is absolutely irrelevant to my being single, but I couldn’t help adding it to my postings. It’s a very important topic to me.

Besides, if we look at it in a different light, whether to go skinny or flared could seriously affect the success of a date. For reals.

First of all I’d like to say, I told you so.

Several years ago, when the skinny jean trend first came to be, a friend and I, both from the era of wide-legged jeans, carried on long and detailed chats about the topic. The skinny jean look was really just beyond our comprehension. For one thing, jeans with a tightening at the ankles and calves can’t help but make one’s butt look bigger. It’s just a matter of physics. Secondly, skinny jeans are skinny all over and can’t help but give you a muffin-top look or sausage-like midsection.

My friend and I however, kept mum on the topic. Skinny jeans were all the rage and we didn’t want to reveal our inner old ladies. We just kept quietly wearing our wide-legged jeans and refused to give in to the skinny revolution.

I felt proud to go against the grain actually because I do like fashion and like to think of myself as somewhat stylish, at times. But I’m a practical fashionista. If a style doesn’t make logical sense to me, and doesn’t seem to have longevity for practical reasons, I just won’t do it.

To me, there was nothing ever fashionably practical about skinny jeans. On really skinny girls, they looked alright, but on almost anyone else they created the look of a beanbag on a pair of toothpicks.

Flared or wide-legged jeans on the other hand, do the exact opposite. They hug the hips and butt creating curves and calling attention to the necessary areas, then widen as they reach the floor. This makes our hips and butt look smaller than they actually are, or at least they’re smaller in comparison to our ankles. Isn’t that what we all want?

This style makes a lot more sense to me. I’m pretty sure that most of us have slimmer ankles than backsides anyway so it seems like reverse logic to try and make our ankles look wafer thin and our rears, thighs and mid-sections like big sausage casings.

With flared or bootleg jeans, I don’t think we ever have to concern ourselves that someone might assume we have a skinny behind and really fat ankles.

Even if our ankles are a wee bit on the thicker side, wide-legged pants will cover that up too. It’s a win-win situation.

The only thing I have to do now is figure out what to do with my newish skinny jeans. But actually, since I never really wore them as jeans and used them more as a legging with boots and a long top or sweater, maybe it’s okay.

In the final analysis, if the question is skinny or wide, my vote is go wide or go home.

(Photos courtesy of the Toronto Star: Long live the flared leg)