Dear Julie: Advice About Taking a Guy Out of the Friend Zone and a Bad Borrower

DAME’s Friendkeeper lays the perfect plan for gauging the romantic interest of a platonic neighbor and assures a chronic lender she can say No.

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Dear Julie,

I want to take a guy out of the friend zone. He’s someone I’ve known for a couple of years now. We’ve always hung out pretty regularly, have long walks and talks, and he happens to be my neighbor, so he helps me around the house and has even done some dog sitting for me too. But now we are both single at the same time and I think there could be something there, but if there’s not, how do I find out without rocking the friendship boat? I’m hoping for a When Harry Met Sally–style ending, but I don’t want to take our interactions from cozy to embarrassed if that’s not the case. Should I just leave it be? 

Loving Thy Neighbor


Dear LTN,

Oh God, don’t you wish you were in elementary school and you could just pass him a note that says, “DO YOU LIKE ME? CIRCLE ONE:  YES   NO” Alas we are out of that delightful period of our lives and have to do things in a more grown-up way. Unfortch, when it comes to affairs of the heart I am deeply 13 years old. I’m sorry but I just want to protect you from potential embarrassment. Here is why: When I was a sophomore in college I was good friends with this guy. We had coffee all the time and laughed hysterically at the same jokes (he did a Meir Kahane impression that you would not have wanted to miss). He wasn’t like totally out of my league, we were comparable looks-wise, he was much cooler than me, but then so was the homeless guy that pissed in the phone booth under my apartment. ANYWAY, I decided to be brave and ask him if maybe we could go out on a real date some time. He was as kind as anyone could be, he said I was a great girl and he thought I was terrific but he’d just started dating another girl in our class and (then the screen goes blank). Now the issue here is this was 1986, approximately 250 years ago, several boyfriends, a marriage and a divorce and still when I think of this event, I want to leap out the window. True I may have a lower threshold for embarrassment than you, but let’s not take any chances. Of course I am not in any way assuming this will happen to you, but I think there are subtler ways of finding out if someone likes you likes you without losing the friend part. Okay here’s what I’d do: Invite him over for dinner—a thank-you for helping you with your dog…who interestingly looks at him kind of like a father (wink). Then you can play “The Closer I Get to You” by Roberta Flack and Donny Hathaway and get really quiet at the part when he sings: “Over and over again I try to tell myself that we/Could never be more than friends/And all the while inside I knew it was real/The way you make me feel…” And look meaningfully in his eyes. Then you say, “Have you ever thought about us…” And if he looks at you happily then you can kiss or something. If he has horror on his face say, “about us selling Amway.” Then say, “What did you think I was going to say?”—and make it like he’s the weird loser.

Okay, pass me a note in gym and let me know how it goes. 

xx Julie



Dear Julie, 

One of my dearest friends also happens to be a terrible borrower. Last year she wore one of my favorite dresses to a wedding and returned it with a stain no dry cleaner’s been able to remove. If I loan her a book I can essentially kiss it goodbye (sometimes she swears she doesn’t even remember borrowing it!). And just last week she left a pair of my rather expensive sunglasses in a gas station bathroom while we were on a road trip, not bothering to mention it to me until I asked for them back. Adding insult to injury, she didn’t even offer to replace them! And yet she somehow doesn’t realize she’s the worst borrower in the world and continues to ask if she can just “take this sweater for the night” or return my favorite bottle of nail polish bottle “after her mani.” Can I teach her to be a better borrower? Or do I have to put my foot down the next time she asks for something? And how do I do that without coming off like a stingy b? 


On Borrowed Time


Dear OBT,

In the words of my sainted father, this friend of yours sounds like a nudnick. I hate the fact that the person who is conscious/responsible has to worry about looking stingy or neurotic. It isn’t right. Maybe you can teach her to be a better borrower, in the meantime lend her NOTHING. If it’s hard for you to be honest just tell her you need whatever she asks to use. Or you promised the book to someone else. If she asks what’s up you can say you love her dearly but she isn’t great about returning stuff. You can say everyone has their quirks—or you can say, “Do you realize you are the worst borrower in the world?” in a funny way or you can say, “I’m not lending anything to anyone anymore, except for a kidney.” I think a lot of us are so concerned about hurting someone’s feelings when we are really angry and it doesn’t do anyone any favors. What you’re really doing is telling your friend that you’d rather preserve your friendship than let this issue take over and ultimately erode the nice thing you have.

xx Julie


Got a platonic problem of your own that could use the Friendkeeper’s advice? Fire away: [email protected]. No situation is too uncomfortable or too small and all details are kept confidential.


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