DR. JILL GROSS
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To Date Him or Not To Date Him?

4/10/2018

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"A man is truly a man when he wins the love of a good woman, earns her respect, and keeps her trust.  Until you can do that, you're not a man."

-Gregory David Roberts

Dear Dr. Jill,

I’m a 35-year-old female who has been making the online dating rounds for a while now. After many dates with many people who were not a good fit, I finally met someone amazing.

On the first date, sparks flew.

We talked about wanting more out of life, being tired of the whole “casual hookup scene,” wanting to settle down, get married, and eventually have a family.


The physical sparks were there too. We couldn't keep our hands off of each other. I ended up staying the night and we ended up having sex. It was mind-blowing!

Sex is something I vowed never to do on a first date.

After one of the most amazing nights of my life, my date and I said goodbye and agreed to go out later in the week. He said he would call or text me to set something up.

A week passed.  Then two weeks. Then a third.


I reached out to him a few times and, each time, he wrote back with brief, one-word answers. I asked about getting together. He responded vaguely and never got back to me.

I was very hurt and confused by his behavior.  Was this the same guy I met less than a month ago?

Anyway. He reached out to me last night, asking to get together. I really like him and would very much like to see him again but I’m still stinging from the roller coaster of the last three weeks.

I don't often meet men I'm so compatible with. I'm afraid of closing the door on something (or someone) with promise.

Should I tell him that my feelings are hurt?  Am I being too sensitive? Should I just accept his invitation and forget the whole thing ever happened? I don't want to scare him off by coming on too strong or by acting needy or clingy. 

Would appreciate your thoughts on what to do.

Signed,
Bothered and Bewildered



Dear Bothered,

Oh girl.

What stands out most in your letter is not that you seem needy or clingy. It's the amount of fear and self-doubt you feel--only a few weeks after meeting this guy!   

I had two thoughts when I read your letter.


The first pertains to the breaking of the vow you made to yourself about proceeding a bit more slowly when it comes to being intimate with someone. This is something most of us either have done or will do at some point in our lives.  So no judgement here.

That said, we need boundaries to feel safe and secure in any relationship, romantic and otherwise. When we behave out of accordance with our own boundaries, it is normal to feel insecure. In this case, I suspect your fear of seeming "needy" or "clingy" is a manifestation of this insecurity.

The second thought I have is about your date's behavior.  In short: it's really bad.

I’m wondering if you feel confused because this man's behavior is the very definition of confusing: hot one minute; lukewarm—even cold—the next.

​Given the first date you described, anyone would be left wondering what the hell just happened. This is not needy or clingy. Yours is a natural reaction to inconsiderate behavior your date has yet to own or apologize for.  This is a big red flag in my dating book. 


Before you do anything, I recommend sitting quietly with yourself and taking an honest inventory of what it is you really want.  

​
Do you want a hot fling or a deeper, more stable relationship with an emotionally available partner? 


Though his words may have indicated otherwise, I suspect your date is capable of offering you little more than a (temporary) good time.  If you decide that you want stratospheric chemistry (aka white hot sex), by all means, accept his offer. 

Just know that, if you have real feelings for this man and/or if you want a real, committed partnership, each hookup with this guy is likely to be followed by an unceremonious thud back into fear, confusion, and yearning. For more on that, click here.


Many of us mistake chemistry for connection.  It’s easy to do. The former tends to be instantaneous, short-lived, and drug-like. The latter requires patience, consistency, and time to develop. Not exactly the stuff that James Bond movies are made of but, in the long run, a much better emotional bet.

Bottom line:  if a solid, stable partner is what you are really looking for, I strongly encourage you to look elsewhere. No man worth his salt would ever dream of leaving someone he cares for guessing about his feelings or intentions.

Here’s to a more satisfying future dating experience!

Yours in health,

Dr. Jill


Dr. Jill Gross is a licensed psychologist, counselor and dating coach in Seattle, Washington. Emotionally unavailable partners got you down?  You deserve better!  Find out how hiring a dating coach can help you have a richer, more satisfying relationship experience. Schedule a free dating consultation today!
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Top 7 Second Date Questions (And Why You Should Ask Them)

4/1/2018

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Love is like a virus. It can happen to anybody at any time.

- Maya Angelou

As a Seattle based dating coach and consultant, I am frequently approached by earnest, well-educated individuals looking for real love.

So many daters these days appear to be supplanting the substantive, slow-cooked intimacy narratives of yore with the relationship equivalent of fast food.

We prefer chemistry over connection. And it needs to be easy, hot, and now.


This can be a real drag for those of us looking to move past a first hookup and on to the complicated process of getting to know the person sitting across from us.

The ability to feel and express emotions is unique to human beings. It is what distinguishes us from lizards. The mutual exchange of feelings is also one of the core components of real intimacy.

So what do we do once we've surpassed the scripted “getting to know you” conversations associated with a first date?

Here are seven questions that will help you coax your second date conversation toward the deep end of the pool:

  1. When is the last time you cried? This question will provide you with a hint about your date’s level of emotional sensitivity. Be cautious of those who say they don’t cry. People who don't allow for the healthy expression of sadness are often skilled at heaping it onto other people (which could be you someday).
  2. What subject or activity makes you lose track of time? A well-rounded individual should have at least one thing they care about. People are more likely to feel attractive and be attracted to someone when they are talking about their personal passions.
  3. If you could change anything about yourself, what would it be? You must pinky swear me that you will think long and hard before accepting a third date with someone who cannot think of at least one thing about him or herself s/he would change if s/he could. Humility is a sign of maturity. Arrogance is not.
  4. What are the top three most defining moments in your life? Our most poignant memories illustrate the relationship we've formed with ourselves. The answer to this question can also speak to your date’s values (accomplishment, resilience, etc.).
  5. If you could go back and do anything in your life over again, what would it be? This question addresses your date’s ability to learn from past mistakes--an essential part of conflict-resolution in a long-term relationship.
  6. Who was your favorite family member and why? Family relationships form the template for adult relationships. Finding out about the person to whom your date felt closest in his/her family allows you to see what values and traits your date will be drawn to in a partner.
  7. What is the scariest thing you’ve ever done? Courage is not the absence of fear. It’s the willingness to feel afraid and do it anyway. Asking this question will help you asses your potential mate’s ability to stretch outside of his/her comfort zone and learn new things.

​There is a time and place for lighthearted, superficial banter. It’s a necessary part of getting to know someone. But, once the small talk has been folded and packed away, these questions will help you take your second (or third or fourth) date to the next level.

And remember: the cornerstone of intimacy is the reciprocal exchange of sentiments. Ask only the questions you’re willing to answer yourself.

What about you? What are some of the best out-of-the ordinary questions you’ve said or encountered on a date date? Leave a comment and let us know!

Dr. Jill Gross is a licensed psychologist, counselor and dating coach in Seattle, Washington. Find out more about how hiring a dating coach can help you have a richer, more satisfying relationship experience. Schedule a free dating consultation today!
Schedule Your Free Consultation Now

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    Seattle psychologist grief counselor and dating coach in Phinney Greenwood North Seattle

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    Dr. Jill Gross is a licensed psychologist, grief counselor, and dating coach. Her coaching and therapy practice is located in the Phinney - Greenwood area of North Seattle in Washington. 

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  • Home
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