First-Date Fears

First-Date Fears

Dear Eve
I think I have a serious problem. I am 24 years old and I have never been on a date. I am going on one in a week and do not want to screw up. I have been looking for this woman for a long time. We connect writing to each other and we feel the same way about each other. What can I do that will spark interest but not scare her off?

Can you give me advise 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, the easier your date will be. Everyone has to start somewhere—and I’ve gotten this same question from people in their fifties— so instead of thinking that “you have a serious problem” or 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, while “past baggage from previous relationships” is one of the world’s biggest complaints, you can feel confident that your lack of experience could actually be a welcomed thing.

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 it turns out to be more, you will be pleasantly surprised. If you expect your soul mate and it 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 that 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” and paying attention; asking questions shows your interest and curiosity. Be prepared to answer your own question. “I’ve done some sailing, but not a lot. One time I sailed in a race…” 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 of any discomfort or lulls in conversation. People are quite understanding when what they understand is 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.

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