Bay Area Dating Advice

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.

Ask Amy Anything!

As Linx continues to grow by leaps and bounds with our membership, we have been getting more and more requests from friends and clients of Linx to ask me anything dating and relationship related.  Music to enjoy for this entry is Justin Bieber featuring Nicki Minaj. Every once in awhile a little cheese it ok. It’s catchy….

We have a new feature on the Linx website where you will see a grey button at the top left of every page. Simply click on it and it will directly port to email where you can ask me anything that is on your mind and I will do my very best to address each one either through an email back to you or as an anonymous Q and A on my blog.

Here are some questions that have trickled in this week into my inbox and my very quick answers in a nutshell.

Q: When is it appropriate to sleep with the guy I am into? We haven’t become exclusive yet and I can barely keep my hands off him. Help!

A: Depending on your personal goals of ending up with this fabulousman, you need to wait till you are exclusive. If you give in and sleep with him as sexy as he is, he will have gotten everything he wants. If it seems pretty clear that he is wildly attracted and into you as well (and respects you and is treating you well outside of the bedroom), I would think it will be pretty natural to have a talk about becoming exclusive. Simply say you are an old-fashioned girl who was raised a certain way and doesn’t sleep around. You also don’t sleep with a man till you are exclusive. If he is into you, he will wait and wait and wait! Good luck! Once exclusive you can crank up The Isley Brothers “Between The Sheets.” 😉

Q: I am a newly divorced dad of 3 young kids and am nervous about getting out into the dating scene. My kids have a mom and I don’t want women to think that I need her to be their mom. What to do? 

A: Dating after divorce can definitely be challenging and present a whole slew of new factors that you never knew were out there. Your first date sound byte to this lucky female is that you are newly divorced and one of your greatest passions are your three beautiful children ages (X, Y, Z). You have joint custody (or whatever your situation is) and they see their mom every other week. On the off weeks you do your own thing and on the weeks you have them you bunker down into dad duty. Although things did not work out with their mom, you have a healthy relationship with her and she is a GREAT mother (never tear your ex a new one no matter your relationship with her.) Then you change the subject and pay your date a genuine compliment and focus on the moment and getting to know her.

Q: I work at Stanford campus and am pretty shy to begin with. When I take breaks for lunch or coffee I see some of the cutest guys ever. How do I go about having them pay attention to me? 

A: My sister and I were walking at Stanford two nights ago and saw a David Beckham look-alike. Her jaw dropped and she was like Ummmmm he is hot and the funny thing is he totally checked her out! So there are gorgeous and brainy babes all over. There are a variety of methods for you to seek the chaps attention.  First dress the part to attract the right guy you want in your life. Be feminine and classy. In my sisters case we were exercising. So in that case, dress in tasteful, clean, and attractive workout clothes. Second, go up to him and ask him a question. If you are working at Stanford chances are you are a genius but in reality there is nothing wrong with sometimes playing a little dumb. I’m not saying to be a clueless ditz, I’m suggesting pulling out your naive card for this opportunity. Ask him where something is on campus. For all he knows today is your first day at work on this big, big, scary campus! Make eye contact, smile, then pay him a small compliment. An example….Hi…I am wondering if you can tell me where Coupa is at the GSB….ohhh..great….(eye contact, lock eyes, smile)….I like your kicks. I’ve never seen Nike make those.  At this point, hopefully you can stike up a flirty convo and see where it takes you. Have fun!

Q: I have a major crush on my boss but he is married with a beautiful wife and baby on its way. I would never do anything to break up their marriage but I can’t stop thinking about him. Is there something wrong with me? 

A: An attractive and confident man is a sexy thing. It sounds like you are human to have developed an innocent crush. Innocent is thinking about him, thinking he is cute, having a soft spot for him while maintaining your professionalism. A crush steps into very dangerous territory if you channel Alicia Silverstone from The Crush and fixate on him to the point where it is inappropriate or ever come on in a sexual manner. You have a strong intuition and chances are you know what is right and wrong. If you want to keep your job, keep your crush benign.

Q: I hate when construction workers and other guys driving by cat call me and make me feel degraded. Should I just tell them to f*ck off or ignore them? As a strong woman (yet a sensual and very feminine one), I feel women need to stand up and let men it is inappropriate to do this. 

A: Yes women do need to stand up for themselves but in this case I think the best strategy to just keep walking. I will share a hilarious scene from Sex in the City when Miranda gets cat called renting  a five-hour Danish documentary on the Nuremberg trial (and a pound of gummy bears to boot….remember?)

(Sleazy construction worker) “Hey, hey, it’s my sweetheart. You’re looking good, baby. Good enough to eat. Hey, where you going, doll ? I got what you want. I got what you need.”

(Miranda) “You talkin’ to me?”

(Construction worker) “Oh, we got a live one, boys.”

(Miranda) “You got what I want ? You got what I need ? Uh-Huh. Well, what I want is to get laid!” 

Ask Linx Anything!

Dear faithful readers,

Although I don’t know most of you personally,  I am thankful that you are reading the blog and hopefully enjoying the random things I post here from Linx HQ. I’d like to get to know all of you better and thus encourage you to comment on any of the entries. Don’t be shy!  And, yes, you can do this anonymously.  I’m going to start a new “ask anything” part of the Linx website where you can submit dating and relationship questions to my inbox and I will answer on the blog, keeping your identity totally and completely anonymous.  So go for it!

Q: ” Amy when is it appropriate to sleep with the guy I am really into?”

A: Although it can be very tempting with hormones firing in all directions, resist that temptation until you are exclusive! If you are serious about love and getting to the goal of marriage in the near future, absolutely wait until you are in an exclusive relationship. 

Our featured song is Enrique Iglesias Tonight I’m Lovin’ You. 

Women make it too easy for guys right and left by having sex  without any sort of commitment. I was horrified, when I was dating in San Francisco, at how casual guys were about sex. “Stay over tonight,” he would say. “Huh?” was my response followed by a “not ’til we are exclusive.”

Guess what? The serious good guys will RESPECT your wishes, beg, and drool like hungry pups waiting for their dinner and the WRONG ones will drive you home that night (thus rejected) saying “ciao bella.”  After he drops you off at home (or hails you a cab or worse yet, you get yourself a cab) chances are he will never call or ask you out again.  Let’s face it, in many ways, you did reject his sexual advance. On the other hand, sister, you are putting your values and needs first, not his testosterone.  

For him, there are so many other girls willing to go downtown and do the horizontal mambo that you can focus on finding the right guy.