When Harry Met Sally

Couple cuddling affectionate on the beach in winter with the sea in the background

As a professional matchmaker, I experience more than my fair share of moments of serendipity, coincidence, and bizarre irony. If only I could share the details of all the crazy stories and situations from the last 12 years of running Linx Dating…

Today, I watched a very interesting situation unfold from within my network, and see a great opportunity to illustrate two very important points about dating.

The story goes like this. A former female client of mine (let’s call her “Sally”) moved last year from the Bay Area to Boston for grad school. I had worked closely with her when she lived here and had actually matched to her someone with whom she had had a significant relationship. She arrived in Boston, single, and has been dating there with mixed success. Though I am not regularly in touch with clients who have moved, I do keep them on my radar, in my database, and in my mind, should a tailor-made opportunity arise.

Separately, my husband has a friend who recently referred a prospective male client to me who is based in Boston (let’s call him “Harry”). After corresponding with the candidate, we both realized quickly that I am probably not the best day-to-day matchmaker for him, given his plan to stay in Boston. However, I offered to do whatever I could for him with my limited Boston network, including introducing him to friends who might have tips about being single in Boston.

It then occurred to me that “Harry” and “Sally” could be a great match and beyond this should no romantic connection transpire, “Sally” could help strategize about ways to date intelligently in Boston.

I immediately reached out to “Sally” to see if she was still single – delighted to hear from me, she said that she, in fact, was still single and would be open to an introduction. I provided a very high-level overview of the potential match – basic biographical information, age, etc. She almost immediately interrupted me and said, “this guy’s name isn’t ‘Harry’, is it?” I said, “well, yes, it is Harry… wow… you know him?” She went on to say that she had had a first date with “Harry” months and months ago, had been interested and attracted to him, but had never heard from him again, then figuring that he had no further interest in her. She asked me to find out from him if she had done “something wrong” that had subsequently “turned him off.” I agreed to ping him to conjure up any intel I could.

I turned around and reached out to “Harry” and asked if he remembered “Sally,” explaining that apparently they already knew each other. “Harry” immediately remembered their date, described “Sally” to a tee, and said he had been interested in her, but had not followed up because he thought that she had no romantic interest in him. I couldn’t believe what I was reading right before my eyes!

After a few emails back and forth, both “Harry” and “Sally” were game to pick up the pieces where they left off. I proceeded then to “broker” a new meeting so that “Harry” could meet “Sally” again and now we’ll see what happens.

What lessons are here for those of you who are single and looking?

  1. COMMUNICATION, SIGNALS, AND GAMES

I live this every day through my clients. Most of you probably know that there is a whole school of dating thought out there around strategic game playing, veiled communication, pickup artist stuff, etc. At the end of the day, no one wants to be bored and find complete predictability in their romantic dating – and it can be very hard to be transparent, vulnerable or open about your feelings early on in dating because you put yourself at risk to be hurt, and you also might worry that revealing too much too soon could either scare off the other person, or make them feel it is too “easy” and not enough of a challenge.

I won’t deny that there can be truth to all of that. But you have to follow your instincts – if you are out with someone and you honestly believe that there is something there, you don’t have to let it ALL hang out, but give the other person a bone. Show them SOMETHING. Whether it’s a flirtatious comment, touch, look, or whatever… or maybe you just say something if you are comfortable. If you don’t, you run the risk of being in a situation that “Harry” and “Sally” were in. And you might never have known what could have been.   So be aware of how you are coming across, and if you are “feeling it”, don’t get too cute or play it too cool or you just might miss out on something special.

  1. THE POWER OF TRUE NETWORKS

Networking is a brutally abused term. It conjures up images of cheesy salespeople exchanging business cards over a superficial exchange of pleasantries and promises to follow up on whatever they might have been discussing.

But true networking is a long-term investment and I am reminded, on almost a daily basis, how hard anyone, whose career is based heavily on networks, has to work to expand, maintain, and nurture the network.   And I believe you have to build your network with TLC over time, with no regard as to how it might benefit you or anyone else in the future. In other words, it is often a selfless labor of love where you must enjoy the journey and know that it will bear fruit in the most unexpected ways.

The most successful real estate agents work hard over years and years to build meaningful relationships that result in repeat business and high-yield referrals. Moreover, they skillfully mine their specialized markets as arbitrageurs of even the smallest tidbits of information. And, in the process, they have hundreds of prospective deals that never happened, thousands of tidbits of advice they gave that netted them no money, and countless moments of frustration. But all of that work nets them a great reputation and plenty of wonderful deals to secure their business.

Linx Dating, in many ways, is no different. Had I not spend the last 12 years building my network this way, I would never have been in the position to allow my brain and my database to lead me to (unknowingly) reconnect “Harry” and “Sally.”

Everything else aside, it is the power of the Linx Network, that sets us apart in the matchmaking world.

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