FOR SINGLES: Four Things To Say on a First Date

black-couple-on-a-dateIt’s hard enough to find a date, but let’s face it, first dates themselves can be tough. With two relative strangers attempting to play the person they wish they were, first dates can be artificial too. While some people believe the game is won by stringing a person along with a set of fantasy projections, only to reveal the truth after they’re too attached to bolt, I’m a pragmatist. I believe that stone cold honesty is the way to win someone’s heart. Communication skills can begin on the first date. But being honest doesn’t mean hurting yourself by spewing your tender entrails without any boundaries. It means knowing what to say and how to say it. Here are three phrases that should definitely be brought to the table on a first date.


1. The thing I’m most proud of is….

Strutting your stuff in an honest display of self-pride is a great way to market yourself to a prospective date. Clearly your date has already sized up the physical package, so it’s up to you to show your interior worth. Feeling proud of an accomplishment that is dear to your heart is a great way to begin to show your value system. Of course, it’s not a good idea to sound like a bragger or to compete with your date. But healthy self-pride is sexy. It’s all in the delivery.


2. Tell me about yourself….

This may sound like an awkward “job interview” style question, but I’m always amazed when I hear that two people spent an entire evening together and talked about movies, restaurants, gyms, celebrities, fashion and food — and never talked about themselves. The topic that everyone knows best is themselves and it can really take the nervous edge off an evening to become a curious journalist and ask plenty of questions about your date.


3. My relationship goal is…

The biggest problem with today’s dating market is that you have players and non-players in the same pool who have very different expectations about what a love life should look like.  Every year millions of dollars are plunked down on dating tables where two people are looking for two different things. These days, you can’t assume that she’s looking for a boyfriend just because she accepted a date. And you can’t assume he wants to someday get married just because all his brothers are married. I’m a big believer in showing your hand. This saves on misunderstandings, hurt feelings, broken hearts, and plenty of wasted money as one date become ten and only then does she reveal that she has no intention of ever getting married or having kids.


4. Someday, I hope to get to know you well enough to answer that question fully. That’s a perfectly honest, complimentary response to any prickly question that crops up in conversation. A first date is too early to become totally vulnerable with a stranger, but this sentence suggests that you a) like the person, b) have boundaries and c) are willing to disclose sensitive information in the future.

One thought on “FOR SINGLES: Four Things To Say on a First Date

  1. Wendy,

    You are the only person that has gotten through my thick scull with regards to dating and slow love. I appreciate you and all you have given me, through your wisdom.

    Thank you,


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