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Three Tips to Finding Love the Second Time Around

Ray and I met for the first time in 2005, having successfully navigated through divorces, both of us with a few “practice relationships” under our belts.

I was 37 and he was 41.

We were both happy singles, but wanted to find our forever love.

We'd both been on our share of first dates before we met, including one guy who admitted to being on the witness protection program, one whose ex-girlfriend showed up at his door pregnant (while I was there), and for Ray, a 1-900 operator.

I'd thought when I got married the first time, it would last forever. Dating after divorce was hard. I was newly back in a city I had left several years earlier. Most of my old friends had young kids and busy lives. The dating pool seemed much smaller. I felt a bit lost and like I was starting from scratch again – both professionally and personally.

Where does an artsy introvert meet someone, when all her friends are paired off?

Online dating seemed like a good idea, as one of my good friends had met her husband online. At that time (2004), there was some stigma around online dating (i.e. “why can’t you meet someone the regular way”), and I remember feeling hesitant to admit I was doing it.

But let’s be real. For singles looking to mingle, online dating is a super-efficient way to meet people (who isn't dating online these days?).

Due to our earlier online dating misadventures, Ray and I both had rigorous screening processes for potential dates that might reach out.

Ray's profile (aka River Heights Guy) was funny, smart, and free of grammatical errors (very important). And in his profile picture, he had a fire extinguisher in his kitchen (very practical). And this gorgeous man was wearing a sexy, ivory, fisherman-style sweater (sigh...).

And he wasn't in the witness protection program.

Ray will tell you that he meticulously crafted his profile like a high-stakes marketing campaign.

And I was the target market.

Our first date was a long talk on the phone (remember landlines?). We played the piano for each other. I sang for him. We had so much in common and marvelled at how we likely would not have crossed paths any other way than online.

Our first "in-person date" was in spring, 2005 at a local pub, The Freehouse. Each Monday, a local university jazz program hosted “the Monday Night Hang.” Students would come to jam with professional musicians, and listeners would cheer them on.

Ray met me at the door. The bar was packed, but Ray noticed a work colleague (let's call him John) sitting in a booth at the front.

John waved us over.

Turns out I knew John too. I didn't tell Ray at the time, but John and I had been on a date several months earlier. The three of us listened to the music and chatted (me mostly with Ray).

Several months later, John asked Ray at work, "did Jackie ever tell you that we went on a date?"


Despite the weird situation, it was a great first date.

Later that week, I emailed Ray to say hi, interested to learn more about this super-interesting, handsome and musical guy.

Jackie and Ray with a mountain view
Tateyama mountain hike (Nagano, Japan) with a beard-less Ray

We went out again the following Monday.

On Wednesday, he invited me for dinner.

I brought a bottle of wine, and Ray had bought the same one for dinner (Wolf Blass Shiraz, green label, which they sadly don't make anymore).

And the rest, as they say, is history.

Jackie and Ray wedding picture
Two crazy kids getting hitched.

If you are looking for love (online or other) for the second time around, consider these three tips.

At first, they may not seem overly romantic, but for us, they were key to finding our forever love.

Tip 1: Keep calm and focus on your own life

Ray and I were both in a good place when we met. Ray had his life. I had my life. We were both happy singles and would have rather stayed that way than pursue a life with the wrong person. We carried ourselves with confidence because we were happy with our lives.

Confidence is sexy.

It can be tempting, when we meet someone and the sparks fly, to start laying out a future together (even if just in your head). Keep calm, get off the wedding websites, and take your time.

Tip 2: There are no "yes signals"

Early in our dating life, Ray told me he'd come to the conclusion that there are no "yes" signals - no indications that a person is "the one" for you.

But, there are "no signals", unmistakable signs that this is not the person for you.

Ray argued that only after enough time with no "no signals", this person might be a "yes."

To which I thought to myself...

"WHAAAATTTT? I'm not clearly a YES? I am a catch, dammit!"

History is full of stories of love at first sight. And the law of averages dictates that some of those relationships will work out and survive the test of time.

But the majority of us easily lose our better judgement if we don't pay attention to the no's - those little actions or words that just don't sit right, but it's hard to put your finger on what's wrong.

Some of these are pretty clear. Like being in the witness protection program. Or when an ex-girlfriend shows up at the door pregnant. Or your partner is in multiple relationships (that you haven't agreed to).

But other "no's" can be more subtle, creep up slowly, and get swept aside, such as...

Pushing your boundaries

Driving a wedge between you and your friends or family

Rolling their eyes (a sign of contempt)

Mocking behaviours

Treating others unkindly

Challenging your values (see tip #3)

And so many more.

Ray once told me that with us, the relationship felt easy. It's not like we didn't disagree or have conflicts, but there was always a willingness to work it out.

We had so much fun together. We felt so much on the same page (and still do).

The relationship just feels so right. Even in the dark times.

There were (and still are) no "no signals."

Formal photo of Jackie and Ray in front of cathedral
Sometimes we clean up real nice!

Tip 3: Know your values

Our shared values - like adventure, family, honesty, achievement, legacy - have been the keystones to our relationship and lifestyle.

One memory stands out. Early on in our relationship, I invited Ray to my nephew's high school play. My nephew was playing in the orchestra and we were all going to support him.

Ray and I started dating in April, and this was late May. In some ways it felt way too early to "meet the family," but in the most important ways, it was the perfect time. I was crazy about Ray and wanted to share this wonderful guy with my nearest and dearest.

I'd dated guys in the past who gave me a definite "no" to this type of activity. In fact, it happened more than a few times after my divorce, and I would always be crushed that they had no interest in learning about my history.

In one relationship, my birthday was the same day as his parents' anniversary. Not only did he forget my birthday (oops, sorry), but also excluded me from his own family celebration.

I was hurt, but I, in my people-pleasing, "I'm too cool to let this kind of stuff bug me," ways, brushed it off as no big deal.

It was a very big deal.

I broke up with him shortly after that day. Happy birthday to me!

Family is important to me, and I wanted my guy to WANT to know and spend time with mine. And I wanted to know HIS.

Ray's response to my family event invitation?

"Of course!"

Jackie and Ray doing multi-pitch rock climbing
Living our adventure value: climbing Slabby McSlabface in Kananaskis

I was giddy (and a bit stunned), given my history. Ray valued family, and it meant the world to me that he was (and still is) excited to see mine.

Know your values. If your early relationship evidence suggests your partner doesn't share them, don't try to rationalize it away.

In July, Ray and I will celebrate 16 years of marriage.

And I think that's enough time to call this a "yes!"

Do you have any tips for finding love the second time around? Tell us in the comments!

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4 comentarios

17 feb 2022

Such wonderful honesty Jackie.... and I agree with the subtle ”no’s”. Thank you for a fabulous and enjoyable read!

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18 feb 2022
Contestando a

Thank you! I’m so glad it resonated! Paying attention to the no’s is life changing! 😊

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Life is a grand adventure, thanks for sharing yours.

I especially like how you remind us to pay attention to the little actions that don't sit right.

Happy birthday to you for taking action and being open to finding your soul mate in Ray.

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18 feb 2022
Contestando a

It is definitely a grand adventure. It was a while to find each other, and I wouldn’t change one of the lessons that I learned along that journey (well, except maybe witness protection program guy 😜).

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