Dear Wendy: A Coke-Dealing Boyfriend & A Serial Monogamist

“I met my current boyfriend about six months ago and there was an INSTANT attraction. At first he was perfect: he would make time for me, we would go out and do things together. He wasn’t like any other guy I’ve ever dated — he was polite, open-minded, caring, funny, and RESPECTFUL. I was the one to kiss him first…he even waited longer than I wanted to have sex with me. Here’s the thing though: he’s a coke dealer. As the relationship has progressed, we’ve broken up and gotten back together numerous times and though we’re together now, and I can honestly say that I’m in love with this man, I hate what he does. We don’t hang out much and he blames it on his “work.” I see him MAYBE once a week… is that normal for people who have been dating for eight months? He tells me he’s going to quit his job one day, but I’m not sure, and I can’t push him to quit because, to him, it’s a nice way of making money. I know he sounds like a loser, but I’ve never been with anyone like him before and I can’t stay away from him. Should I just leave a person who I love and care about because of what he does, and try to find someone with a respectful job?”

Yes, you should leave the man you love and care about, not only because what he does is illegal and could get you in trouble with the law, but also because his “job” dramatically interferes with creating a stable, committed relationship. Let’s forget for a second that your boyfriend’s a coke dealer, and focus in on your relationship with a discerning eye. You’ve been together for all of eight months but have already broken up and gotten back together several times, you see each other at most once a week, and he constantly uses work as an excuse not to spend more time with you (Frankly, I wouldn’t be surprised if he’s got other girlfriends on the side keeping him busy. He already knows you don’t approve of his lifestyle — what’s keeping him from engaging in other behavior you wouldn’t approve of?). Even if your boyfriend were a busy doctor or high-powered investment banker, if what you really want is a committed relationship, I’d advise you to find someone who is more available to pursue one with. A relationship — a real relationship, not just an occasional hookup — takes an investment of time and emotion. It doesn’t seem like you’re getting either of those from him.

Now let’s put his coke-dealing career back into the equation. Do you really think a drug dealer is long-term boyfriend material? Husband material? Father material? What kind of future do you think you can have with someone who sells drugs for a living? And if you really believe he’s going to quit his job anytime soon, you’re fooling yourself. He’s already said he sees his job as a “nice” way to make money, so why would he give that up during a recession when well-paying jobs are so hard to come by? Does he talk about other career aspirations he has? Has he made any moves at all to obtain skills that may make him employable? If the answer is “no,” it’s clear he’s making empty promises to appease you.

Get out now before you invest any more of your time or energy. After eight months, the return on your investment is pitifully low — don’t take a chance of it falling any more. Go find someone else who’s “polite, open-minded, caring, funny,” and has a respectful job. You deserve better.

“I am currently “involved” with a man that I met through my ex-husband and have been friends with for over 14 years. We have very good chemistry as friends and we began feeling attracted to and spending more time with each other over four years ago, shortly after I split with my ex-husband. In that period, I’ve had one relationship that lasted seven months and prior to that, a 2.5 year relationship with the father of my son (no kids from the marriage). In case I’m not making it clear: I do not stay single or uninvolved for very long. The two more recent relationships moved very quickly and both ended badly. Now things are moving quickly with my friend (we’ve recently slept together) and I have been flip-flopping between stopping the situation and trying to have a relationship with this guy. He in return has given me very little emotional feedback. A part of me feels the need to stay single and uninvolved, but the other part tells me to run with it and see if something meaningful develops. I know I need to be fair to everyone involved including myself. Does time focusing on myself mean I have to cut this situation short?”

Color me confused, but if your friend has given “very little emotional feedback” about pursuing a relationship, what exactly is there to “run with”? I would imagine a man who’s known you for 14 years, is friends with your ex-husband, and has watched you speed through at least two relationships since your divorce — one that resulted in a son — might have some feelings about the possibility of getting serious with you. The fact that he hasn’t shared those feelings makes me suspect he knows they aren’t ones you’d want to hear. So if he doesn’t want a relationship, why doesn’t he just come out and say so? Well, because what red-blooded man who has a friend of the opposite sex he’s attracted to and gets regular sex from is going to rock the boat? He’s gonna ride that ship as long as it’s sailing.

Stop sleeping with him — go back to being just friends for the time-being. Focus on yourself and being a mom to your little boy. This man has been in your life for 14 years already – he’s not going anywhere. If things are meant to be between the two of you, it’ll happen eventually, but in the meantime, take a breather from the dating scene and cleanse your relationship palette so you can fully appreciate the next dish when you’re good and hungry.