Four women in four cities take on 365 dates between them. Follow their adventures and misadventures.

8. Nice Guys Finish…? Mr. Wish I Was Attracted To You

As soon as I saw, Mr. Wish I Was Attracted To You, I knew I was going to feel bad about the inevitable: getting rid of him.

His look: Short.

Obviously lied about his height on Match.com.

Stocky. Older. Conservative (he wears a button down the same way my dad does – tucked in).

At least his glasses are edgy.

But Mr. Wish I Was Attracted To You is nothing but nice, polite, intelligent, and down to earth.

We connected on an intellectual level due to similar educational backgrounds and a passion for writing.

Out of all the 3six5dates men so far, I had the most natural and deep conversation with this guy. It did not feel as if we were just checking off boxes for a typical first date chat.

We even brainstormed about reality TV pilots for new shows – starring me!

When I solicited his advice for my own writing career, he said:

“You should be on TV. Your look and personality is captivating. I mean, I haven’t read your writing, but you are made to be a reality television star.”

I thought it was fabulous he could already get me thinking about my dreams.

He is the type who would protect me (he swatted a fly away from my plate) and would always take care of the tab (already paid when I returned from the bathroom).

A guy who really knows how to be “the man” on a date.

He seemed to be an old soul; with his politics and interests – he really did remind me of my dad.

When I told him about my father’s obsession with Frank Sinatra, he excitedly whipped out his iPod.  

Every song on there was by Frank Sinatra!

I wonder if this all turned me off.

He’s fatherly; why would I want to kiss him?

But as we walked home, he pointed to a “really great Italian restaurant” and asked me if I would like to do dinner this week.

I found myself saying yes.

Do you think it is possible to eventually fall for someone who you do not initially find attractive?

Are looks really all that important? What do you think?

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  • Paul Banks

    I think looks are the initial attraction, which is normal. What either
    elevates the relationship is what is inside a person
    (personality,heart,soul, caring,etc). We have all gone out with
    attractive people but after a while we realized there was nothing
    beneath the surface. IMO the best relationships are the ones where you
    start out as friends and develop. When you don’t initially have any
    romantic desires with the person, you don’t hold back on your opinions
    of anything. This allows the other person to see the real no, the the
    artificial you that is exposed during a dating situation. The dating
    situation sometimes doesn’t permit your honesty to flow because of the
    fear of commenting on something that the other person either doen’t
    agree with or deems offensive. 

    • Rachel Russo – Ms. New York

       Thanks for your comments guys!
      Paul:Very good points! I agree, in the long term, physical attraction
      means nothing if the substance is not there. Becoming friends could work
      in favor of eventually creating a romantic relationship like you
      suggest, but, unfortunately, I find both personally and in working with
      clients that many men and women are not open to truly making friends
      with the people who reject them on dates. This seems like a shame. I am
      always up for a new friend.

  • Marc Oromaner

    Marc Says: Rachel, your mind tried to eliminate this guy with an
    “instant discount” as soon as you met him. Why? Because he is a soul
    connection, a true synergistic relationship, and that’s scary because
    he’s not what you expected. It’s a challenge to focus on synergy even
    when you know about it! Look at your own comments: “But ‘Mr Wish I Could
    Be Attracted To You’ is nothing but nice, polite, intelligent, and down
    to earth.” Connecting on this level goes much deeper than an instant
    physical attraction which only fades, a soul connection grows with time.
    “We connected on an intellectual level.” It’s so much more important to
    have a partner you can talk to and connect with than admire how hot
    they are. “I thought it was fabulous he could already get me thinking
    about my dreams.” He is inspiring you to be the best version of
    yourself! That’s pure synergy! Glad to see you are giving this guy a
    chance. I’d like to think that our own discussions on synergy are
    helping to quiet the mind so you can hear the whisper in your soul.

    Readers: To learn more about synergy, check out our “Synergy For
    Singles” page on Facebook.

    • Rachel Russo – Ms. New York

      Marc: I agree with many of your points here as well. It would be scary
      for me to start a relationship with a guy I am not attracted to no
      matter how much synergy we had, because I believe physical chemistry is
      something that can keep a relationship going in tough times. It has in
      my past and at this point, despite my many attempts to give guys like
      “Mr Wish I Could Be Attracted To You A Chance”, I don’t think I could
      “fall” for someone without it. To me, without it, I will never have a
      true romance. I suppose I was socialized, like many other women, to want
      the whole package. If a guy doesn’t do it for me physically, but we
      connect on many other levels, I usually wish to make him a friend,
      business partner, or mentor!

  • Craig

    Alright Rachel not gonna criticize you for not expecting things to work
    out with this guy based only on attraction. I happen to agree, no
    attraction is deff a deal breaker for me. You are right you were much
    less mean on this date.

  • Sam

    I know it’s just TV but I think every woman knows SATC speaks an awful
    lot of truth at times… Just watching the episode where Charlotte and
    Harry first start their “courtship”. Awkward, not what Charlotte would
    ever typically go for. Best relationship in the entire series!

  • Dupree


    Honesty is the best policy.

    “…But as we walked home, he pointed to a really great Italian
    restaurantand asked me if I would like to do dinner this week…”

    You weren’t going to give him a chance. You were just going to use him
    for dinner. You knew that. It wasn’t fair for the poor guy.

    Every girl and every guy deserves to spend their time with people who
    actually are interested in them.

    • Rachel Russo – Ms. New York

       Okay, okay, Dupree! I admit I am a bit of a foodie, and I do enjoy
      dinner dates with these 3six5dates men, but honestly, I am not one of
      those women who goes on online dating sites for free meals. It’s not
      worth it to me to have sit through a meal with a guy that I dislike.
      There were things about this guy that really appealed to me. As my
      nickname for him suggested, I was really wishing I could be attracted to

      • Bobh9876

        “I was really wishing I could be attracted to him!”

        But you’re not attracted to him.  So yes, you are using him for free food.  At least the homeless are honest about what they are.  What’s your excuse?

  • Tom Smith

    Why is it OK to reject a man is he is “short” but when a man says he isn’t attracted to a woman because she’s overweight, he’s “mean?’