DR. WALLACE: I need some help and advice, because my boyfriend lives daily life as if it's one big negotiation! Every time we go anywhere at all, he will "strategically complain" about things and try to get his way with a lower price, a better table in a restaurant, something free or something discounted. At first, I thought this trait was interesting and maybe even cute, but four months into this relationship, now I'm exhausted every time we go anywhere, because half of his focus is on strategic complaining, and the other half is maybe on me.

Watching him go about his negotiations in daily life makes me also wonder about how he's "working me" within our relationship since it's so easy and transparent for me to see his ulterior motives with everything else he deals with in his life. Is there a way I can get him to calm down and give this habit a rest? It seems his mind is constantly calculating every single possible angle to everything in front of him, and he's spending a huge portion of his time and energy trying to get a better deal or outcome for himself 24 hours a day, seven days a week. Help! — Strategic Complaining Is Not Worth It, via email

STRATEGIC COMPLAINING IS NOT WORTH IT: It's going to be difficult to mute or extract a habit from another person that is apparently so deeply ingrained. For whatever reason, he either feels slighted at the beginning of every such situation, or he truly enjoys the discussion or, shall we say, negotiation that he constantly finds himself involved in and dealing with.

You can absolutely seek to have a conversation with him about the topic at the most "strategic" time you can select. However, be prepared for your request to not be so welcome from his perspective or point of view. If you're very tired and exhausted at this point, can you imagine dealing with years or even a lifetime of witnessing such situations on a regular basis? If you haven't invested too much in this relationship, this may be a good point for you to evaluate the overall benefits versus drawbacks of the relationship from your specific point of view.

HE'S GOOD LOOKING BUT PRESENTS HIMSELF AS UNKEMPT

DR. WALLACE: I'm a female college student, and my new boyfriend, who I've been with for almost two months, is very good looking. But what's interesting to me is, now that I know him much better and see him on a really regular basis, how often he goes out in public in an unkempt manner.

It's almost like he dresses down sometimes on purpose, as he'll have a shirttail sticking out, mismatched clothes, shoelaces untied, his hair a total mess or whatever he comes up with on any particular day.

I've thought of bringing this up to him, but I haven't so far because things have been going so well between the two of us and I don't want to potentially introduce unforced conflict. Why do you think he does this (if it is a conscious decision)? I've considered that he may not be aware he's doing this, but somehow I think he's doing it on purpose. Should I say anything about this to him, or just continue enjoying our time together without rocking the boat over what likely is a fairly trivial issue? — He's Good Looking but Unkempt, via email

HE'S GOOD LOOKING BUT UNKEMPT: It would be interesting if you could arrange a formal or at least semiformal attire "event" for the two of you to attend. You could arrange that and, without saying anything, silently watch his preparations or at least see the presentation he would put forth in such a situation.

Your letter didn't mention it, but I'm curious: When you first met him, did he have his personal look a little more together, or was it similarly unkempt at the time of that first conversation? Many males take their personal look quite seriously and put a lot of time and effort into it, but for whatever reason efforts to look sharp are not part of his style, at least at this point in his life.

Since things are going very well between the two of you interpersonally, rather than bringing up a direct conversation, you could do small subtle things around the edges to see how he reacts, such as tucking his shirttail in, handing him a comb or brush before you two go out, etc.

In the end, as long as his personal hygiene is good, how he opts to present himself in terms of clothing and hairstyle is something you shouldn't worry much about.

Dr. Robert Wallace welcomes questions from readers. Although he is unable to reply to all of them individually, he will answer as many as possible in this column. Email him at [email protected]. To find out more about Dr. Robert Wallace and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at www.creators.com.

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