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First Date Fears

I’ve never been on a date and don’t want to mess it up. What should I do?

August 6, 2009
Eve Eschner Hogan, M.A.

Can you give me advice on this? Please help me!

Congratulations on your upcoming date! It sounds like you have already sparked her interest, now, take a deep breath and relax. The more relaxed you are, the more yourself you are and the easier your date will be. Everyone has to start somewhere—and I’ve gotten this same question from people in their 50s—so instead of thinking that something is wrong with you (which is a difficult mindset to feel confident with), reframe your thinking to honor that you waited until you were ready to start dating. Also, because “past baggage from previous relationships” is one of the world’s biggest complaints, you should feel confident that your lack of experience might actually be welcomed.

The biggest challenge I see facing you is not being so anxious for a relationship that you create one where one should not be. Remember, this is a date, not the date. Try not to put pressure on yourself for it to be perfect. You will have a lot of dates in your future, so just look at this as a fun opportunity to get together with someone whose company you (hopefully) enjoy, and it will be fine.

Control your expectation that she is the one that you’ve been searching for, because, until you’ve spent some time together—in person—you won’t know that for sure. If you expect to meet a friend and she turns out to be more, you will be pleasantly surprised. If you expect your soul mate and she turns out to be “only a friend,” you will be disappointed. The most likely thing to “scare her off” is if you come across as if you are sure she is “the one” and start planning your future together before you could possibly know. She wants to know that it is her you are in love with, not your imagined version of her.

One of the biggest mistakes people make when they meet online is they build the relationship by sharing deeply through communication, discussing their hopes and dreams and then they get face to face and suddenly don’t talk anymore. When a relationship is developed through deep communication, it is really important to keep that level of communication going.

Continue to ask and answer questions. Before your date, think of some of topics that you would like to explore based on what is important to you and what you already know about her. It is okay to revisit old conversations that you wrote about now that you are face-to-face. You can even say, “You said in your emails that you like to go sailing. What kind of sailing have you done?” Repeating what you read shows you were “listening.” Paying attention and asking questions shows your interest and curiosity. Be prepared to answer your own question. “All you are really doing is transforming the written into the verbal and visual.

Don’t be afraid to tell her the truth. “I’m sorry if I seem a little uncomfortable, honestly, I’ve been so busy with school (or whatever) that I haven’t really dated much....”

By letting her know what is truly going on with you, she will likely be more supportive. People are quite understanding when they know the truth.

Let me know how it goes!

With Aloha,

Intellectual Foreplay Question of the Week:
How old were you on your first date?

Love Tip of the Week:
There is nothing more romantic than someone who sees the real you and loves you—no matter whether you stutter and stumble, or whether you are suave and sophisticated. The key to love like this is showing them the real you. Be authentic. (Here is a hint: You’ll have to let down your ego shield to do it.)

Eve Hogan, author of How to Love Your Marriage, Intellectual Foreplay, Virtual Foreplay, and Way of the Winding Path, is also the proprietor of The Sacred Garden, a nursery and healing sanctuary in Makawao. It is open 10 a.m. to 5 p.m. daily. For coaching or speaking events, call (808) 573-7700. Website: Blog: Send questions to



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