Dating Advice: 8 Tips For Striking Up a Conversation Without Striking Out

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author

dating advice

In my Love Essentially Column, published today in the suburban Chicago Tribune publications, I offer dating advice on ways to strike up a conversation, in other words, pick-up lines that aren’t cheesy!

Pick up Lines Don’t Have To Be Cheesy by Jackie Pilossoph

Ever been in this situation? You’re out at a bar or restaurant and you see someone you find attractive, and who you’d like to meet. The problem is, you don’t know what you could possibly say to the person that doesn’t sound rehearsed, stupid or just plain old cheesy. You fear that whatever you come up with, the person will think you are desperate or strange. So, you do nothing. He or she ends up leaving, the opportunity is missed and later that day or night, you’re kicking yourself for not making a move.

Approaching someone and or delivering an effective opening line (also known as a pick-up line, let’s be honest) isn’t easy. But if what you say is effective, your reward can be priceless: the beginning of an exciting, new relationship that may lead to the end of your search for Mr. or Ms. Right.

Even as a dating and relationship columnist, it’s difficult for me to offer advice on how to approach someone and what to say. As outgoing, friendly and full of words as I am, I turn into a complete mess when put under pressure to start a conversation with a cute guy, trust me.

So, I recruited the help of Barbie Adler, founder and president of the Chicago-based matchmaking company, Selective Search. I first asked her why men and women have such a difficult time approaching someone they want to meet.

“Everyone has a fear of rejection and they don’t want to set themselves up for failure, having their feelings hurt or being embarrassed in front of their friends,” said Adler, who started Selective Search 15 years ago. “Everyone knows all the cheesy pick up lines and no one wants to use one because that’s not who they are. They don’t know how to go about it while being their authentic selves.”

Here are Adler’s eight tips for success when approaching a potential romantic interest:

1. Get your head out of your phone. The only reason to have your phone out during a night out with friends is if you have children who might need to reach you. Otherwise, be engaged in the evening and focus on the environment. In other words, don’t be on Facebook and other social media sites, and stop texting all your other friends. It’s a turn off! Put your phone in your purse or pocket and forget about it!

2. Women: smile and be approachable. When a bunch of women go out for a girl’s night, they don’t realize that a large group can be intimidating and overwhelming to men. So, if you see a guy checking out your group, smile at him. Let him know it’s OK to come over and say “hi.” Or, what’s wrong with YOU walking up to him and starting a conversation? Nothing!

3. Compliments are never out of style. But, they have to be sincere. Also, it’s better to compliment shoes or a handbag or a smile versus a dress or the woman’s body. It’s more respectful.

4. Direct can work well. “Hi, I’m Dave, may I buy you a drink?” Simple and honest. No games.

5. Try situational humor. Let’s say you’re in a really long line at Starbucks and there’s a cute guy in front of you. Say something funny about the line. Be friendly, witty and smart.

6. Play matchmaker for your friend. There’s nothing wrong with going back to Junior High School for a few minutes by walking up to a girl and asking, “Are you single? I think you should meet my friend.” Even if the person isn’t single, he or she will take this as a compliment and appreciate it. If it works, you’ve just done Barbie’s job!

7. Be both confident and sincere. This is a winning combination.

8. Don’t take rejection personally. The person might be involved with someone, they might have issues that have nothing to do with you, or you just might not be their type. Remember, you are someone out there’s type!

 In closing, I can’t resist sharing these hilarious pick-up lines I found on Instagram. I would highly suggest NOT using them!

  1. Is your name WIFI? Cause I’m feeling a connection.
  2. On a scale from one to ten, you’re a nine and I’m the one you need.
  3. If you were my homework, I’d throw you on a table and do you all night.
  4. Is your body from McDonald’s? Cause I’m lovin’ it.
  5. Did you get a parking ticket? Cause you’ve got fine written all over you.
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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

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