Dear Prudence

A Real Catch

I can’t stay broken up with my homeless drunk of a boyfriend.

Get Dear Prudence delivered to your inbox each week by signing up in the box below. Please send your questions for publication to prudence@slate.com. (Questions may be edited.)

Got a burning question for Prudie? He’ll be online here on Slate to chat with readers each Monday at noon. Submit your questions and comments here before or during the live discussion.

Dear Prudence,
I broke up with my long-time boyfriend for the fourth time yesterday. He’s a manipulator and a drunk and a narcissist but also fun and charming. I don’t have a lot of friends in this town, but I have joined some clubs and do some volunteering at an art gallery in order to see people. Seeing a therapist helps, and I also go to Al-Anon, but I don’t have a lot of friends here and I work at home. My ex has lots of homeless, unhealthy, alcoholic friends who hang out in the park. I am basically his job. He hangs out with me so he can afford his lifestyle of drinking in the park and still keep a roof over his head. I met him a few years ago in a larger city where he had normal friends and family members. He doesn’t speak to any of them anymore. He is no good, but I am kind of a weakling. Please advise.

Advertisement
Advertisement
Advertisement
Advertisement

—How to Make a Breakup Stick?

Honestly, I’d advise you to move. This might be what you were hoping I’d say. I’d also advise you to stick with therapy and Al-Anon if you relocate, both of which are excellent resources when it comes to ending a painful relationship. You work from home, so you could presumably take your job with you, and you don’t know a lot of people in the town you live in now, which suggests to me you moved there with (for?) your ex-boyfriend. Now you should move for yourself. I don’t mean to say that leaving town is a suitable response to the end of every relationship, or that it can replace therapy, but in this case I think a great physical distance between the two of you would do you a world of good.

Advertisement
Advertisement

The worst possible outcome would be to continue as you are, going through all the pain and difficulty of a breakup every few months, then watching your ex bounce back to you when he needs money or a shoulder to cry on or a place to dry out for a few days. You would be maximizing your suffering while preventing yourself from being able to move on. You don’t currently trust yourself to make this breakup stick, and you don’t have a special attachment to the city you’re living in now. So find another city, one that you have friends in, and move there. Enlist their help and support as you build a life without your ex and continue to find your own strength.

Advertisement
Advertisement

* * *

Dear Prudence,
Recently I went out with some friends I hadn’t seen in years, one of whom turned the conversation to religion and eventually the Holocaust. It turns out he believes that the Holocaust never happened. I was embarrassed that someone I went to school with all my life could believe such a thing. He further claimed that God was black and racist against whites and therefore we should hate whites, too. (He is neither white nor black.) I told him I couldn’t continue to discuss his beliefs, as they were completely wrong, but he persisted, and eventually I told him that until he can bring the Bible and show me where God commands people to be racist, I wouldn’t have this conversation. He called my bluff and said he’d bring it over. I grew up Catholic but now consider myself agnostic, so his arguments about God didn’t bother me that much. But because all I could think during our conversation was, “How dumb are you?,” it made me wonder if I was the one being intolerant. Am I? Now what do I do when he brings me the Bible?

Advertisement
Advertisement
Advertisement
Advertisement

—Holocaust Hoaxer

The only mistake you made was getting drawn into a debate with a Holocaust denier. There is no earthly reason you should continue an exegetical debate with someone who, old friend or not, declines to acknowledge the existence of one of the most thoroughly documented events of the 20th century. You had to suffer through an unpleasant conversation with a former classmate and current crackpot; don’t compound your suffering by trying to engage with his pet racial theories by close-reading a book you’re not convinced has any divine inspiration. Remember that “the Devil can cite scripture for his purpose,” and decline his offer to continue your biblical debate.

Advertisement
Advertisement

* * *

Dear Prudence,
My long-term boyfriend works as a professional film crew member with long hours and an unpredictable schedule. I’m uncomfortable with the level of intimacy that crew members develop with each other on long shoots. Two years ago, one of his co-workers frequently Snapchatted him and posted flirtatious status updates on social media. He insisted nothing was going on, and we had a huge argument. More recently, we went through a rough patch while he was away for six months. I caught him deleting text messages he was sending to another woman. He says that he was just asking for relationship advice and he only deleted them because I fly off the handle whenever he talks to any other woman. He claimed he also asked a male co-worker the same questions. I don’t think it’s appropriate for him to have very close friendships with women, but I also don’t like him confiding in random male co-workers about our relationship. I have a jealous streak and acknowledge this may not be a healthy attitude. However, it’s not uncommon for crew people to hook up with each other, and I’m afraid I won’t be able to tell if he’s cheating on me due to his erratic schedule. He feels that I am too domineering. How can I be understanding but also establish healthy boundaries? We’ve discussed counseling but haven’t gone yet.

Advertisement
Advertisement
Advertisement

—Infidelity Anxiety

Your problem is a serious one but not insurmountable (the main problem being your jealousy and attempts at surveillance, not your boyfriend’s relationship with his co-workers). You say that it’s not uncommon for “crew people” to hook up on shoots, but your boyfriend isn’t “crew people.” He’s your boyfriend. And he’s never cheated on you, but you seem to be treating him as if it’s only a matter of time until he does. If you think he shouldn’t have close friendships with women or develop deeper friendships with his male co-workers (who are not “random”), you’re not leaving him very many outlets outside of your relationship. Add to that the fact that you periodically turn your relationship into an inquisition whenever he goes on location, and you’re creating a paranoid and unpleasant environment for the both of you.

Advertisement

It may be that your jealous nature and his inconsistent work schedule are truly incompatible, but if your relationship is otherwise good, follow through on your discussions about counseling and go together to develop saner strategies for dealing with jealousy and making each other feel secure. There may be reasonable things he can do to reassure you, but you have at least as much to gain by corralling your own dark thoughts—surely you can’t enjoy being constantly tormented and beset by doubts.

Advertisement
Advertisement

* * *

Dear Prudence,
My boyfriend is amazing, but his parents have a loose concept of hygiene. I’m admittedly a bit of a germaphobe but this weekend his mom made brunch while announcing she was sick, coughing over the plates, licking her fingers before touching food, using paper towels from out of the garbage to wipe off food prep surfaces, and using the dog’s water bowl (with a secondslong rinse) as a serving bowl. I love this guy and want to spend my life with him, but I can’t fake indigestion or lack of appetite for the next 10 years. If I talk to him about it, he’ll just say he eats their food and he’s fine. What do I do?

Advertisement
Advertisement
Advertisement

—Gross In-Laws

Oh, this is a finger-licking bridge entirely too far. In future, you have carte blanche permission from me to say things like, “If you’re sick, Marilyn, I’d rather you get some rest and not run the risk of passing anything on to the rest of us—I’ll order takeout” and “Marilyn, I’d prefer not to eat something out of the dog’s bowl” when the moment arises. The sheer disruption posed by your simply saying “I’d prefer not to eat something out of the dog’s bowl” might jolt everyone into a temporary return to sanity and remind them all that humans and dogs deserve separate, unique bowls. You are well within the bounds of appropriate behavior to speak up and object when you see flagrant health code violations in a family kitchen. (If that makes you germaphobic, call me Howard Hughes.)

Advertisement
Advertisement

That said, you should still have a conversation with your boyfriend about your feelings, if for no other reason than to give him advance warning that if the same situation arises again, you won’t be eating his mother’s cooking. If he tries to fob you off by claiming he’s fine, then say, “That’s great for you, but I’m not comfortable with it, and I’d prefer it if your mom would wash her hands and stop serving potato salad out of the dog’s water bowl.” The time for delicacy definitely ended when you saw your future mother-in-law fish used paper towels out of the garbage to wipe the counters.

* * *

Dear Prudence,
I have been married to my husband for over 20 years. He is a career military man, and I’ve followed him all over the world and loved every minute of it. We are due to retire soon. For years, he’s been saying he wants to retire close to his family. The problem? I don’t like the area of the country where his family lives. I don’t care where we live, but I don’t want it to be there. This isn’t because of his family: They are lovely people. But where they live it is cold nine months out of the year. There isn’t much in the way to do except hunting and fishing, and I don’t care for that. For years, when this topic has come up I’ve gone along with it, because it seemed so far away. But now that it is becoming a reality, I just don’t know how to open this conversation. I don’t think “Honey, I’ve lied to you for years” would go over too well.

Advertisement
Advertisement
Advertisement
Advertisement

—Leaving the Military

It’s not a great opener, you’re right, even if it’s a better alternative than spending your retirement in active misery. It sounds as though you’ve spent the last 20 years very effectively going along to get along, but that’s not a strategy that will serve you as well in retirement as it did while being a military spouse. Flexibility and the ability to handle change are excellent attributes, but you seem to have conditioned yourself to not express your true preferences. You clearly do care where you live—at the very least, you’d like to retire somewhere warmer with at least a few more potential recreational activities. This is a fairly reasonable request! Don’t start the conversation with “I’ve been lying to you.” Tell your husband that as the reality of retirement approaches, you’ve been giving more thought to what you want out of the next phase of your life, and you’ve realized you’d be miserable living someplace where you had to stay indoors for nine months and fish for three. You’ve spent the last 20 years supporting your husband whenever he’s had to move for his work. It’s not too much to ask that you take, as a couple, both of your desires into account when figuring out what to do next.

Advertisement
Advertisement

* * *

Dear Prudence,
I recently met a man who is kind and loving—everything I want. We’ve been dating about six months, and things are great. There is, of course, one problem. He has false teeth, and mediocre ones at that. Not only do they not fit him correctly, but they sometimes make his breath smell horrible. He knows this and brushes and uses mouthwash religiously to combat the issue. But a permanent fix would mean new false teeth, which would cost a lot of money he doesn’t have. I am thinking of offering to loan him the money, but I’m not sure how he’d react. We haven’t been going out for all that long, and I’m not sure if there is any etiquette in these situations. Do you think I should offer a loan to him for this?

Advertisement
Advertisement

—New Guy, Bad Teeth

Your letter’s got everything: a new relationship, money troubles, and false teeth. I cannot imagine a version of this story where loaning him the money works out well. As you say, you don’t even know your new boyfriend well enough to guess how he might react to your offer, which suggests you also don’t know what type of borrower he’ll be. Would he be resentful? What if he couldn’t afford to pay you back according to schedule—is he the type of person who would be clear and upfront about it, or would he try to avoid you? What if he ended up spending the money on something else? What if you loaned him the money and he got better false teeth but still suffered from chronic bad breath? There are far too many variables at this early stage of a relationship. If you can afford it, and you really see a future with him, and you think he would appreciate the gesture, consider making it a gift, but don’t become your boyfriend’s loan officer. There’s a chance he may not accept, in which case your remaining option will be to kiss him only after he’s thoroughly brushed.

Advertisement
Advertisement
Advertisement

* * *

Dear Prudence,
About a year ago, my family stopped speaking to me after I left their extremely conservative, insular religion. I grieved for quite some time, but I respected their wishes. I am getting married in a few months, and my heart is breaking. My father won’t be walking me down the aisle. My mother never helped me pick out a dress. None of my old friends will talk to me. So I’m not going to have any of the traditional events that lead up to the wedding. While I love my fiancé’s family, who have been supportive and welcoming, I can’t seem to get out from under this cloud. I feel petty for wishing that I’d be able to experience all of these traditional events, since I should be utterly grateful I’m even going to marry the most fantastic man ever, who has been extremely understanding through this whole process. What do I do? How can I get past this? How can I show my appreciation to my future family by marriage, without feeling that there’s still emptiness?

Advertisement
Advertisement

—Family Matters

You can be grateful for the love and acceptance your fiancé’s family has shown you while still mourning the loss of your own. There’s nothing petty about wishing your parents could be there on your wedding day, and your fiancé’s family isn’t a replacement for your (still quite recent!) loss. You’ve been cut off from every single person who cared for you as a child—no matter how unkind and cruel their decision was, it’s not easy to shrug it off and decide you’re better off without them. But you are better off without them—if they can’t love and support you regardless of your religious beliefs, then their love is deeply conditional—but that doesn’t mean it won’t hurt. If you try to force yourself into experiencing only gratitude for the family you do have, and don’t allow yourself to grieve, you will be doing yourself a disservice.

Advertisement
Advertisement

Be kinder to yourself than your family was. Give yourself time to come to terms with your loss. Consider seeing a grief counselor, because what you’ve experienced is not unlike a death. You can be grateful and devastated, grateful and empty, grateful and bereft. If your in-laws are as loving and supportive as I think they are, they will understand that the loss of an entire family isn’t something one gets over within a year and that your joy in becoming a part of their family will sometimes be mixed with sorrow.

* * *

Dear Prudence,
I have a wonderful problem. My boyfriend’s parents treat me like one of their own, and we get along fantastically. We live several states away and plan to get married in the next year or so. Whenever we visit his parents, they are endlessly generous with meals and experiences. They are planning a big family vacation overseas this summer and have included me in it, with all expenses paid. They are also very casually affectionate, signing group emails as “Love, Mom and Dad” and ending group phone calls with “Love you guys!” I appreciate this, but I am nervous about accepting such generosity from nonfamily members and hesitate to express casual intimacies with them. I have no qualms about calling them Mom and Dad after I marry their son, but we’re not even formally engaged yet! I send thank-you notes and flowers regularly for their generosity. My question is: Is that enough? Do I risk coming across as cold-hearted or selfish for not being able to reciprocate financially or emotionally?

Advertisement
Advertisement
Advertisement
Advertisement

—Lots of Love, but Not Family Yet

I wish I could put you and the previous letter-writer in touch, so you two could commiserate over the problem of feeling uncertain and unready about the love others have shown you. (I have a lot of sympathy for your situation!) I don’t think you’re doing anything wrong. You’re responding warmly and politely to their generous overtures, but you happen to be a little more reserved than they are, and you’re a bit more tentative about establishing intimacy. That said, if you and your boyfriend are already planning to be married, I don’t think you have to wait for a formal engagement to flip the Family Switch “on” in your head. You’re not cold or selfish, and it doesn’t sound like they’re being overbearing or trying to pressure you into expressing a familiarity you don’t feel. Let yourself warm up to them in your own time, bearing in mind that you’re already in many ways a part of their family and don’t need wedding ring as proof that you deserve their interest and affection. It’s with great pleasure that I say I think all of you are doing just fine.

Advertisement
Advertisement

Discuss this column with Dear Prudence on our Facebook page!

More Dear Prudence Columns

Red-Letter Day: The notes my dying mother wrote to me a decade ago are haunting my life milestones.”
Present Pain: If my husband doesn’t put more thought into his gifts, I’m going to cry.”
Runway Bride: I hate my unfashionable—and nonrefundable—wedding dress.”
Can’t Take a Joke: My family mercilessly teases to show affection, but my boyfriend doesn’t get it.”

More Dear Prudence Chat Transcripts

The Last Temptation of Bob: Prudie advises a man who doesn’t trust himself with his wife’s flirtatious sister.”
Goading Granny: Prudie advises a man whose now-dying mother enjoys haranguing plus-size loved ones.”
Love in the Time of Cancer: Prudie counsels a parent whose 16-year-old feels pressured to support her stricken boyfriend.”
Choose Life: Prudie advises a woman with two special-needs sons who wants a third child—with genetic counseling.”

Advertisement