Single With Siggy: Putting Up Walls

Romance guru Siggy Flicker advises Jess Lipson, a Philadelphia human resources director who finds it hard to soften up.

woman in black dress
(Image credit: Marie Claire)


Trouble expressing vulnerability.

JESS, 35: I've been told I'm intimidating. And I'm more comfortable with myself now than ever, which I think escalates the problem.

SIGGY: You're passionate and sure of what you want. Sometimes you have to play the part. It's not about acting dumb; it's just having a glass of wine before a date.

JESS: I was seeing a friend of mine, but I cut it off because I was getting too close. Now he's dating a young girl and wants me to meet her!

SIGGY: Unacceptable!

JESS: He likes me and won't admit it.

SIGGY: You're putting up walls and protecting your heart.

JESS: Because I've been hurt before.

SIGGY: This isn't anything you can't handle. People are coming back from Afghanistan with no legs—you can't deal with your friend? Say it like it is: "How do you expect me to meet her when you know we have feelings for each other?" Your biggest problem is showing your vulnerability. But that's what makes you human. You can do it your way, but that isn't working.

JESS: I love my girlfriends, but I'm like, enough! It almost feels detrimental because they're single, too. We sit at the bar together.

SIGGY: If I'm looking for a job and all my other girlfriends are, too, do I take them on interviews? No. Pretend your best friend is meeting you and she never shows up: "My girlfriend's late—guess you guys are stuck with me!" Men will surround you. But first you need to come clean with your friend—you need to tell him your feelings and cut off your relationship. Practice expressing your vulnerability with him!

JESS: I'm doing it tomorrow! I can't wait to see what happens.

Two weeks later, after following Siggy's advice…

JESS: I told him our friendship is over. I said, "I'm sorry, I can't do this because I have feelings for you." He wasn't happy.

SIGGY: Did you cry?

JESS: Yes.

SIGGY: I'm glad. That's where the healing begins.

JESS: I feel like a weight has been lifted. Then Saturday I went to a bar by myself! I made some new friends, and everyone wound up talking to me.

SIGGY: Did you say, "I'm waiting for a girlfriend"?

JESS: No, I just watched the game.

SIGGY: Jess, this is great. If you feel comfortable doing this, the world is yours. One day you'll be there and you never know who'll walk in. Now you can let go and have fun.

JESS: To hear this from a perfect stranger was a kick in the butt. It may take some time, but I want to soften up. Now I just have to practice.

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