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A Clever compliment is truly an art form. Why? It is the right mixture of sincerity, intention and guile. In giving a compliment, you’re not only expressing appreciation, but encouraging future behavior which conforms to your liking. Do not read this wrong- this is not manipulation- it is, to coin an over-used decade old buzz term- a form of “positive reinforcement”.

It goes so much deeper than the dynamic between men and women- this concept transcends simplicity and applies to all relationships. I am going to site a few examples I overheard over the weekend and in one case tell you why it was worthless and how a Clever person would go about relaying a similar compliment.

I was at a bar, waiting for my friend and a woman was waiting for what I over heard her explain to the bartender was a first date with a friend of a friend she’d met a few times. She appeared nervous- had put what amounted to no effort into her transition from work (office job- sensible attire) and had already belted down two glasses of wine “to calm her nerves”.When her date walked it- he eyed her, waved, came over and they did the awkward half hug, attempt to kiss on the cheek and then part quickly with nervous laughter thing during which the following dialogue (if you can call it that) took place.

“Hey! You look nice.” (if nice means she is not wearing pajamas and is clean)

“So do you.” (there is nothing, truly nothing that annoys me more than the utterance inserted into a conversational turn slot. This goes for “I love you” … “I love you too”. “I miss you.” … “Me too.” Arrrgggg. How about this instead- insert a pregnant pause, generate a thought which does not mimic the other person’s and then issue it forth).

How a Clever Guy would have begun this exchange. (Disregarding the fact if I were the Clever Guy, I would want to say- “Oh, I’m sorry you didn’t have time to change, do you want to drop by your place on the way to dinner?” HA!)

“Hi there! Thanks for meeting me.”

A Clever Girl would respond, “I was really glad to hear from you”.

If the “you look nice” is entirely perfunctory (which it obviously is since the term is so overused no one even hears it anymore) and they don’t really look that nice, skip it and wait for an opportunity to compliment later.

A Clever Girl might enjoy a man’s unshaven face, and since it is later in the afternoon, she might say “Thank you for not shaving before you met me, the shadow works for you.” This will not only relieve him of the chore of shaving before he sees her, but knowing she likes it will be aware of it- thinking he looks good will bolster his confidence and likely translate to giving a compliment back. Thank goodness, in this case he can’t say- “you too.”

The point to all this is the compliment needs to be inspired- which means you need to be paying attention- admiring, analyzing, being aware of the other person so when the opportunity presents itself, you are prepared. A well-crafted compliment will leave an indelible mark on the complimentee and have them awaiting more.

A most Clever Mommy dazzled me at the park today while I was reading. Her daughter looked at her and said, “Why are you smiling, Mommy?” Her mom knelt down to receive her at the bottom of the slide and looked her in the eye. “ Because when I see your smile it makes me so happy.” Her three year old child launched herself into her mom’s arms and I became a little choked up when they fell over- broke into peels of laughter- both of them with their eyes closed- embracing the moment. The exchange had all the critical elements of a perfectly executed compliment. It was inspired, her mother felt compelled to relay it, it wasn’t hollow “you are pretty”, it reinforced future behavior “when YOU smile it makes ME happy” and the acknowledgement and eye contact led to some intimate contact for both of them. Never did mom complain about the dirt in her hair or being squished- they were in the moment and the appreciation for each was obvious.

No one expects a poet- just one who is not blind or so self-absorbed as to not observe the person they have chosen to spend time with.

At the same bar, a married couple walked in and since it was a bit chilly- the woman had a wrap on. She went directly to the restroom and upon her return- he helped her remove her wrap (very gentlemanly). Her back was to him and when he saw the tremendous expanse of skin the back of her dress revealed- he allowed a finger to trail down the center of her back- as if unconsciously. When she turned, this Clever Guy said, “You are, without a doubt, the sexiest woman I have ever met.” I was proud of him for a number of reasons.She bore no resemblance to the “sexy” Hollywood is selling- she was attractive, but would barely turn a head. He seemed unable to keep from caressing her back lightly in acknowledgement. His compliment came from the gut- almost breathless. This told me a few things about their relationship. She dresses for him as well as for herself (perhaps because he is SOOOO appreciative of her efforts), she likely captivates him on many levels amplifying her sexiness (which runs so much deeper for some than how one looks in lingerie) and they were very connected.

The best way to compliment the person you are with is to pay attention to them, to listen and to ask questions. Why? It makes them feel good and if you’re lucky- they will return the favor. In doing so- staying focused- you will find so many things to compliment.

In case you are just learning how to appreciate and spit one out, statements such as those below qualify (think of them as compliment training wheels).

“Wow, that is a really interesting perspective …”

“That is a great question.”

“I’d never thought of it that way …”

“I appreciate you making time for drinks tonight, I know you’re really busy.”

“Dad, I saw the movie Flags of our Fathers over the weekend and, well, we’ve never talked about your experience in the military. If you are comfortable talking, I’d love to hear.” (This is a compliment of immeasurable worth as you are showing interest, preparing to devote time to listening to another person’s experiences).

I had a woman tell me the other day she felt silly complimenting the man she began seeing because he is so handsome and charming- “he must hear it all the time”. I know this translates to a high pressure situation for men and women alike- but don’t panic- if there is that much content to work with …

OK, so she has dimples and a fantastic laugh- look for the nuances of that smile. For example- when she seems shy does she do a closed mouth smile- during which her dimples become impossibly deep? Tell her. Or, when he makes you laugh, tell him how witty and entertaining he is. Ask who designed her dress and tell her the designer did so with her in mind- it fits flawlessly. Tell her the backless shirt she selected elevated the evening or that her shoes have left an impression. Take note of his hands- are they purposeful (translate that to how they will feel when they fall upon you at some point) are they random and playful when he talks? Tell him how expressive he is when he’s talking about a subject he really enjoys. Or say- “So, your parents are hot”- haha. That should get a laugh and you are telling him how attractive he is without saying the obvious.

It just isn’t that difficult. Here are some great adjectives for those of you who can’t seem to move beyond “beautiful” or “handsome”.

Riveting, intoxicating, inspiring, alluring, striking, CLEVER, enthralling, provocative, evocative, stunning, engaging, enchanting, captivating, mesmerizing, hypnotizing, charming, seductive, scintillating, beguiling, radiant.

Keeping in mind- none of these adjectives work if you don’t know what they mean nor do they work like this “you look radiant”- that is a cop out with Clever intentions. Instead- “You’re absolutely riveting- how did you learn so much about …” “Are your eyes green?They seem to change before my eyes. It’s quite mesmerizing” “I hope you aren’t this charming when you’re trying a case- no one would pay any attention to what you were saying. It would be mistrial based on the fact the attorney is captivating”.

A mother and daughter walked into- you guessed it- the same bar- and approached the daughter’s friend. The friend smiled at the mother and with great purpose said- “Holy cow!You look fantastic. Did you ladies tear up Dallas today to find the perfect outfits?” The mother beamed, obviously felt special and even more so when her own daughter followed up with- “Doesn’t she look amazing in burnt orange- goes perfect with her hair.” So much better than, “You look so nice!”

I’d asked the bartender for a recommendation on wine because I’d heard about Pinot Gris and wanted to try it. He guided me- let me try a couple and once I selected one was genuine in asking how I enjoyed it. When my friend arrived I paid out and waited until the bartender was free- I looked him straight in the eye and said, “I just wanted to thank you for helping me with the wine, I really appreciate it.” He looked surprised and said, “You just made my night.” We both walked away feeling validated and valued.

It doesn’t matter who you are complimenting or acknowledging, put some thought into it, make it relevant and purposeful and you might receive the same. If you don’t you will still feel good at having spoken such words of import over others.

The anti-thesis of the person who either never compliments (we don’t like these people) or offers trite acknowledgement is the “over complimenter”. This person is usually the master of the trite platitudes. “Oh, I like your shoes”, “you look pretty”, “this is good”, “I had fun”, “you are smart”. You know this person, they make your teeth itch to be around them because they are full of insincere compliments- so when they turn their focus to you and unload an arsenal of obvious statements- they might as well not be speaking at all since they already offered the same to everyone else in the group. Count on the over-complimenter to say “take care” when you all part ways.

It should be a great day for a great many Clever people who are not only giving Clever compliments but feeling good about it! Tomorrow I will be giving some holiday gift ideas for men and on Wednesday the same for women.