6 Ways To Keep Your Cool In Awkward Dating Situations

6 Ways To Keep Your Cool In Awkward Dating Situations.jpg

Sometimes you just don't know what to say!

We are all looking for love, and finding your one-and-only usually starts with a date.

Most of us have been on dates and had something we wanted to say or ask, but didn’t know what to say to the guy — because we felt too awkward.

I hear all the time from my women date coaching clients that sometimes they just don't have the right words, or worry about how something will come out.

So, in the early stages of getting to know someone new, while trying to get through sticky moments (i.e., he gives you a passionate hug and his unintentional body language gives away just how much he likes you!), it's tempting to give in to your fears and let someone who might have been your true love leave your universe.

But, regardless of who you end up falling in love with, you won’t get there without a few misfires. So don't give up too quickly.

I was on a third date with someone I really wanted to impress, and we were going to a holiday party for his work. I thought things were fine until we arrived at the event, and when he came around to open my door we both saw a significant portion of my long flowing dress had been locked outside the car door while driving!

I wanted to crawl in a hole, and was so embarrassed tears rolled down my face from nervous laughter.

But throughout the night, he periodically lifted the hem of my dress “to save me from myself”! He was a good man, and his empathy for my goofy plight helped me to save face and have a fun night. It also wasn’t our last date.

Have you been in any of these typical scenarios while on a date, or in a new relationship?

  • Your food comes and it’s not prepared the way you asked for it.
  • You go out to dinner and are seated next to your ex and his girlfriend.
  • Feeling embarrassed about your body.
  • Discovering he’s a great guy but a bad kisser.
  • Struggling to figure out the money stuff —  who pays for what and when?
  • Figuring out how to set —  and keep —  boundaries that are right for you.
  • Feeling scared to share that you’ve had a mastectomy before being intimate.
  • Discovering that he's cheap but appears to have enough money.
  • Facing issues around sex and intimacy.
  • Being put-off or embarrassed by the way he dresses.

Being strong and confident from 9-5 is not usually a problem, yet when it comes to a date whom you want to like you, old baggage creeps in. Anything from fears of messing up, chasing him away, being judged, or looking foolish overwhelm many of the women I work with.

You can even be generally fearless in your approach to life, until the part of you that feels unworthy, or doesn’t trust your gut, puts you in a stranglehold.

But here’s the thing: Many potentially vital, exciting, and loving connections have fizzled and gone flat, not because of what was said, but because of what wasn’t said.

Being quick to think when you’re blindsided isn’t easy, nor is sitting down and having a planned talk about something that’s bothering you.

It takes skill and practice.

Mindfulness is something you can give yourself that will enable you to gain these skills. It is the practice of intentionally focusing on the present moment — and accepting it without judgment. Mindfulness is fundamental to emotional and physical well-being, happiness, and feeling more connected to others.

More life-changing benefits are: better regulation of your emotions, greater self-compassion, and developing self-reflection — which enables you to be more in touch with yourself.

Can a good date be salvaged once it’s gone south?

When my coaching client, Sheri, began seeing me a year ago, she had just come out of a 12-year relationship with an emotionally abusive man a few months prior. She is a very savvy, attractive, competent woman with a high-powered career that involves a lot of socializing.

But when it came to expressing her needs on a date, she wilted.

She told me, “I don’t know what happens. I become a little girl, afraid of making waves, feeling guilty, being rude, and him seeing that I’m unlovable. I freeze and don’t say anything over the dumbest things.”

In a recent coaching session, Sheri told me that after her 3rd date with Jack, she invited him in for a cup of tea. Their first two dates had been great; they went hiking and to a concert. There was chemistry, a mutual sense of humor, and good conversation. They both wanted to see where this relationship went, and Sheri made it clear that she needed to take things slow.

Now, in the middle of an enjoyable conversation, he leaned over and kissed her. Looking like she was shaking off the memory, she told me she expected something of a “slower start!”.

She was totally taken aback and didn’t feel that being a bad kisser (temporarily) was a “deal breaker” —  if he could learn how to kiss the way she liked —  which is totally teachable, by the way.

But she was clueless as to how to handle it.

She wondered if she hadn’t made herself clear, but also felt like he didn’t listen to her.

There were a few words of apology about the misunderstanding, and that they had a good time, and then he left.

But what if she had said to him, “Whoa, Jack – that really took me by surprise. Do you remember that I said I want to take things slowly?” He would probably have said something like he thought it would be okay, or apologize. But Sheri could have continued; she had nothing to lose. “Jack, I’m really enjoying getting to know you, and would like to go out again, but I need to trust that when I tell you something about me that you’ll remember it.”

What would it look like to say something difficult to a new dating partner and NOT feel like you made a mess?

It would look brave, honest, imperfect, real, vulnerable, and — when appropriate —  humorous.

According to a recent article in Science Daily, researchers at the University of Turku found that social laughter increases the release of endorphins in the brain, promoting and reinforcing social bonds. The effects of the endorphins in the brain are pleasurable and calming and might signal safety and feelings of togetherness. Allowing yourself to be a little vulnerable rather than too self-sufficient or always pulled together is important to be aware of in relationships. It softens you, and draws him towards you, bringing out his masculine side and desire to be protective.

Being up front, however much you fumble, is not making a mess. It’s being human. 

Life is messy and the important thing is to keep muddling through it.


Here are 6 tips that will help you say what you need to say —  and move on with confidence:

1. Stay present, focusing on what you want to say.
Practice mindfulness and mindfulness meditation. Be conscious of your breathing. Getting oxygen to your brain helps keep anxiety at bay.

2. Speak slowly and intentionally.
If you freeze up, just pause and say you lost your train of thought.

3. Remember that humor is a great connector.
It’s okay to laugh at yourself. In fact, it's an attractive trait!

4. If this is something you have strong feelings about, do your best to stay aware of, and manage your emotions.
Acknowledge your discomfort openly, but move forward with what you want to say.

5. Don’t look for his validation and approval.
You’ve got your own!

6. Be kind, clear, and firm.
Having empathy while still maintaining your boundaries is a win-win, and hopefully you can move on with more trust and understanding between you. Most guys don't want to be jerks, or even know that they are jerks. If he's really crossed a line, end the date as easily for you as possible and leave. Call Lyft if need be.
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We all want to be loved, and none of us want to be rejected. Don’t be afraid to do what is right for you. Even if you are confused, and don’t know what you want to do, you probably know what you don’t want to do. Trust your intuition, and stay close to your message. If you like him, nothing is sexier than confidently drawing a line, and giving him a second chance before banishing him from the castle.  


Dr. Sue Mandel is a psychologist and dating coach who specializes in relationships and the psychobiology of love. She brings 27 years of unique experience helping individuals and couples find and keep love in their lives. To have Dr. Sue help you with your dating dilemma and how to say it contact her to schedule your FREE 20-minute consultation. To learn more visit www.DrSuesConnections.com or email her at drsue@drsuesconnections.com.

This article was originally published at YourTango.com