What to wear to build rapport?

I have a date with a new guy tonight — an advertising agency owner who lives in a nearby laid-back resort town. We had a fun, interesting first conversation two days ago and he asked me to join him for dinner at a midrange restaurant.

Now I must figure out what to wear.

I think women fret about this more than men. While some men may consciously choose to wear a shirt they’ve been told looks good on them or brings out their eyes, I think many don’t give a lot of thought to what they’ll wear on a first date. They may debate to don a sports coat or not, or take off a tie if coming from work.

But women seem to be more conscious of what messages they send off with what clothing. I don’t mean to imply that a lot of women obsess about their attire, but I think most put some focus on what impression they want to give and which clothing will telegraph that message.

So I look through the closet. I want to choose something that is fun and flirty, but not too revealing. I know cleavage is now considered an accessory, but I don’t want to send the wrong message on a first date. Since my date is in advertising, he’d probably appreciate something more fashion forward and colorful than a drab conservative look.

Do you do this? Do you try to match your attire not only to the venue, but to the man? And of course, it has to be congruent with who you are.

Why not wear whatever you darned well feel like, no matter what you know about the man? Why try to wear something that you think he’ll find appealing and similar to the style you think he’d find comfortable?

The answer: to build rapport quickly. To begin the evening, and perhaps the relationship, without friction. We know men are visual. How you look helps set the tone for the evening. Of course, how you both act and what you both say play a huge part.

In college I took a psychology course on Neurolinguistic Programming (NLP). A mouthful, I know. The concepts were initially developed to help therapists build rapport quickly with patients so they would relax and not hold back expressing their thoughts. The work has now been adapted and taught to help people build rapport with others, whether in personal relationships or for business.

One of the key tenets of NLP is to initially match the behaviors and language of the person with whom you are speaking. While I find this can easily be overdone and seem almost mocking and manipulative, done subtly it does get people to open up and relax. So my theory of wearing clothing that my date would find to his taste fits into this matching practice. While I clearly want to be myself, I also know the importance — especially on a first date — of building rapport.

How do you strategically choose to build rapport? Do you plan your outfit based on wanting to look and feel good, as well as taking what you know about your date into consideration? What factors do you consider as you plan your “look” — especially for a first date?

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3 responses to “What to wear to build rapport?”

  1. nysharon Avatar

    You should wear what makes you feel good and what is appropriate for the date. What I would wear for a casual dinner date in a resort town would be a breezy skirt and tank, or jeans and a dressy top either topped with a sweater/jacket for modesty that can be taken off if you feel comfortable. Sexy but in a sophisticated way–but that is what feels good for me. Guessing what your date would like is hard to do, and if you feel attractive you will BE attractive. Def no MAJOR cleavage you want him to notice your eyes and not your …….! It can also come off as desperate. As you probably know, studies show first impressions are the most important. Building repport has nore to do with listening and conversational skills and how comfortable you are in your own skin, than how you dress. But if you don’t make it past first impressions, it isn’t gonna matter.

  2. Ellen Avatar

    What to wear? For sure, something comfortable and something that I feel good in. What else? A big smile, a cheerful attitude, a kind spirit, and an open heart! That’s what draws a man to us, I promise.

    xo Ellen

  3. Alan Avatar

    What to wear, hummm… Care for a guy’s opinion? What you wear does say things to us guys but it is usually the negitive things that cause the unwanted impression. For example, Friday night I went out to play some pool and dance at a local country bar. Firday nights are not as busy as Saturday nights and I’m not interested in the “meat market scene” but do enjoy socializing. An attractive women walked up and asked to play pool. I first noticed her smile, which included all facial features. She was dressed moderately with blue jeans and a top that showed a little cleavage. This was attraction stage and it worked. She asked me later as I walked her to her truck if I would meet her the following night for more dancing and pool. I do not consider this a first date but was very impressed with the fact that she wore a top the next night that covered herself completely. Even though there were several guy’s flirting with her as we played pool, her clothes and body language said she had already attracted the guy she is interested in. If you want a confident man in your life, then dress and be confident in yourself. I think confidents is extremely sexy! If that seems to hard right now, try practicing and remember that tying your shoe wasn’t that easy at first…