What I have learned from 25 first dates . . . .

So I am back in the water, dating (online) again. It is one of the reasons I am leaving the country! Not really, but I will say that dating in your thirties is a minefield.

My parents have been married forty-three years and exemplify generosity and partnership.  You often hear people say some twist on this sentiment: “…if someone truly loves you, they never want you to change.”  With more experience than most, my parents will say, “…what exactly is so terrible about change?” With that attitude, I’ve watched them evolve together, not out of obligation, but because the other person was worth the effort.  

Being insanely fortunate to have these role models, I grew up believing in the value of committed relationships. I also subscribed to the idea of marriage as a destination that magically makes life easier and happier (cue, bluebirds chirping). I am not sure how this myth got so deeply engrained, but “Happily Ever After” was waiting out there for me; I just had to find “the ONE”. So I followed Oprah’s advice and set my intention: marriage and family. It did not seem like such a complicated desire.  On that note, I dated my college sweetheart for eight years and then rolled right on into a four-year relationship with my ex-husband.  No pause. No break. I was stuck on a pre-set channel: wife.

I actually met my ex-husband on Match.com, on what was my first and only online date (until recently). At the time, I bragged that I was somehow an online dating expert.  Well, I am clearly no expert. To say the least, I was shocked to have a marriage last less than two years, especially since my mindset was “forever”. I am extremely humbled. I am sorry. And I am changed.

Although difficult, I have never looked back and know divorce was the right decision for both of us.  Divorce is acknowledging separateness and in an unexpected way, this has been a great gift. For me, the myth of marriage has been debunked; it is not a magical destination or finish-line, of sorts. My pre-set channels have been cleared.  I think this sentiment captures it best:


“Love is as love does. Love is an act of will – namely, both an intention and an action.  Will also implies choice. We do not have to love. We choose to love.”

– M. Scott Peck, The Road Less Traveled


While being single comes with all kinds of mixed emotions, it also presents the opportunity for me to refill life intently. To be clear, I am 100% a romantic at heart and very much want companionship and partnership. I continue to firmly believe that the most interesting relationship is the one you stay in and develop. Over the last year, there have been plenty of days when I feel ready to date. There are other days when I want to wrap myself in a blanket and listen to David Gray; swiping and scrolling through profiles feels like an exhausting full-time job and I might have acute carpal tunnel aka “Tinder Finger“. Finally, dating implies the desire to connect with someone; but, truthfully, I am fighting ‘relationship PTSD’ and am a bit afraid. So the waters are murky.

But no guts, no glory. I summoned my inner Sasha Fierce and signed up for the trio awhile back – Tinder, Bumble and Match.com.  I have been on about twenty-five first dates. Here’s what I learned so far:

The Post-It

Be open-minded, but within reason. I am not a gal with an unwieldy and impossible checklist, but there are a few things I won’t do without. Actually, I can fit them on a post-it note and no, not in size four font.

Rule number one: If the post-it doesn’t hold true, move along. For example, I went on three dates with a delicious 41-year old lifeguard. I mean, this guy was red hot. At one point, I asked him what his “goals” were and the response, “I have no goals”. It was hard, but NEXT!

Rule number two: While finding the right person is paramount, I am best suited for someone who wants kids and family. In my experience, a relationship where the big values aren’t aligned is like pushing a giant boulder uphill. My most recent hopeful date told me (twenty minutes in) that he didn’t want kids (who needs small talk).  When I expressed that I did, he said “You’re 35, what are you waiting for honey, you better get started.”  Points for honesty. Not so hard, NEXT!

Avoid the cartoon

One of the first guys I matched with early on was the captain of a ship. He spent thirty-five days at sea followed by thirty-five days at home. We met just as he had shipped out and talked incessantly via email, text and phone. I suggested a Skype date, but he was adamant about meeting face-to-face for the first time. I anxiously awaited my sailor’s return; very black and white movie, right? We continued to share our life stories electronically and thirty-five days later, I was seriously dating the most incredible cartoon.  I had the perfect guy, but he was based on pixels. Unfortunately, he had recently been relationship burned and was not ready for anything serious, including meeting me in human form. I pictured the Titanic sinking as I deleted his texts, emails and pictures. As a famous cartoon, Donald Duck would say, NEXTH!

There are so many variables, with chemistry among the most important and least predictable. Ever since my rookie mistake with the sailor, I’ve avoid the cartoon. Better said, I am building expectations based on experience, not emails and text messages. I learn more in the first five minutes of a date than I do in hours of emailing and texting. Paying attention to the facts (love, through intention and action) will help me steer clear of the myth.

Jersey Shore?

After about a month on Tinder, I made a general rule not to go out with anyone who has a shirt-off photo. I also am avoiding guys who lead with “hitting the hot tub” as a good first date. Hot tub, is it 1985?

These two rules eliminate about one-third of the online pool.  Shocking and Progress!

Timing is everything

Pretty early on, I matched with a great guy; the chemistry was there, conversation was on-point, we laughed and the big things seemed to be in place. We had an A+ first date at Milo & Olive, but on the second date the conversation took a nose dive. He talked about his cholesterol medication the ENTIRE time. I am fine with illness, but I was bored to death by this Lipitor lover.

As I reflect on this date, I must say there were definitely a few good guys that never got a fair shake because of MY timing. From across the table, it was probably crystal clear that my heart was broken and timing impossible. Ironic, in hindsight, that our dinner was centered around “heart health”. Sigh, NEXT.

Not too high; not too low

I’ve been on about twenty-five first dates so far and it’s a bit like searching for water on a desert island.

The hardest moments have actually been managing disappointment when a connection is there, but my feelings are not reciprocated. Like Tor, the guy from The Netherlands, that did not feel as strongly about me as I did about him. Or the gent that liked to take long walks, during which we talked and talked. I was so fond of his company, and yet, he was headed out on his own road trip of self discovery.

Based on my limited experience in the on-line dating world, I’ve found 90% of my dates have been genuinely good guys in search of a relationship (of some sort). The catch is chemistry that bubbles up and life timing that aligns. This math keeps my expectations in check. But it also makes me hopeful.

Aha moment:  There are plenty of good people out there; chemistry and timing are the great variables. So I’ll rely on my post-it and love, as intention and action, to sort it out. And if all else fails, there are always Dutchmen!




  1. Wow Rissa! Can’t say enough how much I’ve enjoyed reading your posts. I so appreciate your honest reflections and of course your witty sense of humor. Thank you, talented friend! Just awesome!

  2. Rissa,

    I am sure by Dutchmen there is no pun intended 🙂

    You could always go old-school like I did when I hit the match.com scene. I hated the texting and social media part of dating, not to mention the 8 billion first dates ( which as a guy was expensive!). So when I met my wife I actually asked in the beginning if we could simply talk over the phone the first few times. That way I figured if we could hold a conversation and we looked forward to wanting to chat, than going on a first date would be worth our time.

    She did say it was weird at first, however, it worked! We had a blast, first date was great, and we didn’t look back.

    Have a great trip and was great to catch-up a couple weeks ago!


  3. Rissa

    You know I’ve had my fair share of bad match.com dates and some not so bad ones but none that really stuck till, because of you I went on match one last time and met Rich ( seriously the dream boyfriend) I pinch myself everyday and literally have thrown my arms up and pronounced to the universe “thank you” and “it’s about time”. Timing and being open to someone different ( as in not my typical foreigner with a bad ass look ) is everything. The blog is amazing entertaining and knowledgable. So excited for this moment in your life it will be life altering and forever a memory you will never forget or regret. Thank you for inviting me to share a small portion of it. See you in Bali girl ❤️

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