Should You Go On a Second Date with Him?

I read this quote recently: I love that feeling of being in love, the effect of having butterflies when you wake up in the morning. That is special.  ~ Jennifer Aniston

I love her, and no offense meant, but how has that butterfly-thing been working for Jen so far?

During my 35-plus years of loneliness, heartbreaks, dating, love and finally marriage, my relationship with butterflies has changed a lot. Back in the day, when I met that unique man with a certain look and cocky confidence, I’d go weak in the knees. And if he made me laugh and showed me even the slightest bit of interest, that was it. I was a goner. Ahhh…bring on the butterflies.

It was exciting and I loved the feeling. That is, until I didn’t. Because every one of those guys were fleeting connections who left me disappointed, confused and convinced that yet again I missed my chance at love. Why was it that all the guys I liked (and there weren’t that many) didn’t like me??

This was the pattern until I finally understood the difference between a good man and a good date. I learned that a man who could make a spectacular life partner may not be the most skilled dater. And many men who can wow the pants off you on a date absolutely suck at being a partner. (Yes, I meant that somewhat literally.)

It’s because of this epiphany that after seven years of marriage, every day my husband gives me butterflies, though they are the grownup kind. Like recently when I had to fly home from Missouri in the middle of a cross-country road trip after throwing out my back – big time. After my husband wheeled me to the plane (yes, via wheelchair), he drove home alone to Los Angeles in record time to be with me.

Once home, he stayed in bed with me for two days. He physically supported me any time I needed to move, served me food, tried to make me laugh and showed sympathy with my every moan and groan. All this with nary a complaint nor expectation.

The first time he propped me up and guided my hunched-over old bod to the bathroom, I looked at him and felt some serious butterflies. And it wasn’t my pain meds. It was the realization that this man was here for me, for better or worse. He actually adores me – even the highly unattractive, cranky, useless and vulnerable me.

So what gives you butterflies? How do you look at the men you meet, and what do you use as your measurement for judging his worth as a potential partner?  Do you look for that attraction or that “it” on the first date? You know…that “thang” you can’t really explain? Is your benchmark that exciting conversation where it all just clicks? If he’s too nice, does he turn you off? I mean, come on…we all want that edge, don’t we? Those are the fun dates.

My coaching client Mary, who is 44 and has never married, came to me believing there were no quality single men left to date…especially after 40. She wanted to get married and was having the same experience I used to: she wasn’t meeting men who gave her butterflies, and the few who did never worked out.

Like me, Mary always believed that the sign he could be The One was that nervous, unexplained excitement you feel that either happens quickly or never at all. On her first dates if she didn’t feel that chemistry, she would cut the date short, go home disappointed, put on her jammies and continue dreaming about Mr. Butterfly-man.

I helped Mary deepen her definition of what a good man looks like: someone with whom she could see herself happily spending the rest of her life. She also realized that she had been using this measurement since she was in her teens and it had never served her. She was waiting for love to sweep her away, and that only left her alone.

Mary quickly came to see my truth: that a good man could be camouflaged as a not-great-date and that it could take some time to uncover love and attraction between two people. In the first month of our work together, Mary dated three men, two of whom she dated three times. In these men she saw worthy qualities that could possibly mean they’d be great partners. That meant possible future butterflies, so she gave them a chance.

None turned out to be The One. (That’s what dating is, btw: a bunch of “no’s” before that one super “yes.”)  So what, you say? Who cares about this if he doesn’t turn out to be Mr. Butterfly-man in the end?

Well, here is what Mary now has that she never had: hope. She is no longer waiting for that one elusive man to show up and instantly rock her world. She now sees that there are many quality single men looking for smart, independent, over-40 women like her and that with an open mind and heart, she will find him.

I get asked this question all the time: When I’m not feeling that excitement, how do I decide when to go out with him again? Do I have to go out with everyone more than once? Here’s my standard answer: Butterflies be damned! If he doesn’t spit while he eats or insult your mother, if the idea of touching him doesn’t gross you out…go out with him again.


Here are some other good indicators that you might be talking to a man worthy of another date:

  • He asks what you’d like to do on your date. (I know this annoys some of you, but it really is a GOOD sign. It means he wants to please you.)
  • He shows up on time, enjoys himself and happily pays for your date. (And you, of course, graciously accept.)
  • If you share something important about yourself (and you should without expecting him to ask) he listens and seems to care. (It’s not necessarily a bad sign if he doesn’t ask you many questions. He may be nervous, thinks it rude to interrogate you or just doesn’t have the skill set.)
  • He respects your personal space.
  • He is kind to wait staff and others around you.
  • He seems to care about what you think about him.
  • He seems to expect you to treat him with respect and kindness.

Butterflies come from so much more than the color of his eyes, the cut of his suit or how hard he makes you laugh. Just about every woman who I’ve helped find love after 40 will tell you that the guy she is with was someone she never would have looked at before.

I realize that the idea of being helped to the bathroom doesn’t sound romantic; but we’re talking real life here, not the movies. Like myself, Mary and countless other women, if you can open yourself up to a new way of judging men and go on more dates with the idea of getting to know the man in front of you, you will find opportunities and hope you’ve never had before. And, that, girlfriend, is exactly what leads you directly to love.


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