Dear John: Okay To Date Your Ex’s Sibling? Depends On The Sibling
Tuesday, April 15, 2014
I broke up once and for all with an on-again off again girlfriend I dated for a couple years. (This was a couple of months ago.) But her younger sister emailed me recently to get together for a drink and a “talk,” and I’m looking forward to it and very anxious about it also. We were pals and we would do stuff together like Christmas shop for her sister and it was fun although there was never a hint of anything at all beyond a sisterly friendship. But we got along great and being a guy, I can’t lie and say I’ve never thought about what it would be like to be with her. (Just so you know, I am 38, my ex is 36 and her sister just turned 30.) So anyway, I got this email from her and I have no idea what it’s about, but I’m thinking it’s the obvious thing and she wants to see if we both might have stronger feelings for each other than we’ve let on. Is this cool, though, as far as her being the sister of my ex-girlfriend? I have mixed feelings about it, and I have some friends who say yes and some who say definitely not. My ex used to drive me crazy (and I did to her), but I really don’t have any desire to humiliate her or hurt her or anything like that. But I’m almost 40, I want a family, and I don’t feel like I can rule anything out when I already know I get along well with this person, you know?
On The Fence
Dear On The Fence,
The situation you’re describing could work, or it could be an epic disaster. Which one it is depends entirely on the people involved – what their motives are, what their relationship is like, and what kind of people they are. There’s not nearly enough information in your letter for me to know any of that, so I’ll give you my perspective, but it’s up to you to decide what to do with it.
The positive scenario is that your ex’s sister is genuinely attracted to you and regrets the fact that she knows you only because you dated her sister, but she understands life can me messy sometimes. Before contacting you, she would have talked to her sister about what she was planning, if not to get her blessing, then to at least prevent her from being completely blindsided by it. She would have assured her that this is something that she only began thinking about after the two of you broke up. And she would have really listened to your sister’s response.
At the other end of the spectrum is the possibility that this isn’t about you at all, and you simply represent an irresistible opportunity to express the anger and resentment the younger sister has been harboring toward your ex for years. You may not want to hurt or humiliate your ex-girlfriend, but that may be exactly what her sister wants to do.
So which is it? Obviously, I have no way of knowing that. If you sincerely believe the former description applies, then I don’t think dating your ex’s sister is wrong, but you should be aware that even under the best circumstances, there are bound to be uncomfortable (or worse) moments with relatives, mutual friends, etc. It would be a difficult situation, especially at the beginning. There’s no getting around that.
If there’s even a chance it could be the latter scenario, though, then the answer is obvious: dating her would be a terrible mistake.
One last thing to note is that you do sound like you’re getting a little bit ahead of yourself. All she has said is she wants to get together for a drink and a talk, right? This may be what you think it is. But I’d let her go first.
My wife’s best friend from college and her husband are coming east and want to know if they can stay with us a few days. Neither one of us wants that to happen because when they were here last two years ago, the husband (well, all of us) had too much to drink one night and made a pass at my wife. He did it when no one else was around and my wife didn’t tell me about it until after they left. She was more amused by it than embarrassed. You couldn’t come up with a person my wife would be less likely to be attracted to than her friend’s husband. What I mean is that this wasn’t a big deal for my wife and me, it was more of a joke, but we still don’t want him staying here on his next trip to town. My attitude is, we open up our house to you and that’s how you treat us? Okay, that won’t happen again. My question is do we make up some excuse to give my wife’s friend, or do we tell her the truth? Part of me hates the thought of making up a convincing lie that prevents them from staying with us but still lets my wife and her friend see each other, having to remember not to say anything to give away the lie, etc. Why should we have to do all that? Easier to say in so many words you can’t stay here because your husband’s a jerk. Even though he did what he did, though, I don’t want to put any stress on her marriage. For all I know, that was the only time he ever did anything like that. What do you think? Lie, or truth and consequences?
Dear Unwilling Hosts,
I wouldn’t worry too much about devising a convoluted explanation for why they can’t stay with you. Your wife should just say something like, “Ooh, the 15 th? That’s not really a great time for you to stay with us. We’ll be around, though, and I’d love to have an opportunity to see you. Let’s get something on the calendar.” That should be the end of the discussion. If your wife’s friend presses her for an explanation, though, I don’t think there’s anything wrong with being honest about what happened. Drunk or not, this guy did what he did; it’s not up to you to cover for him or to determine how big an issue it is in their marriage.
Quick, simple question: I’ve started dating a guy and he’s a super guy, funny, emotionally and financially stable, considerate, even handsome…except for the fact that he’s just too too hairy! At the risk of TMI, when we’re intimate, half the time I feel like I’m petting him! He doesn’t seem the least bit self-conscious about it and he seems very comfortable with himself, so I don’t know how to raise the issue of hair removal or even if I’m right to do so. I would hate to hurt his feelings or make him self-conscious and isn’t self-acceptance and not buying into our looks obsessed culture a GOOD thing? Maybe I’m the one who has to change…I’m open to that, too…but one of us does, because all I know now is that when he’s undressed it’s all I can notice or think about. What should I do??
Hair There & Everywhere
Dear Hair There & Everywhere,
I agree with you that his comfort with his body is commendable, but I don’t think you’re shallow or superficial for wishing he were a little more meticulously groomed. I’m sure a lot of women – most even – would feel the same way. And I think most men would want to know what they could do to make themselves more attractive to their girlfriend, assuming their girlfriend’s expectations were reasonable. Whether you’ll hurt his feelings depends on how you present your question – and it is a question, not a request. Tell him you’re curious how he would look if he were a little less hirsute, and ask him if he would consider trying some type of temporary hair removal. Tell him about his options if he doesn’t already know what they are (probably not, judging from your description), and let him know that if he doesn’t like the results, it will all grow back (although the implications of that for your relationship are a subject for another letter). Keep it light, be supportive, and I think there’s a good chance he’ll give it a shot and like the results – especially if he knows you like them.
John is a middle-aged family man from Providence, Rhode Island. If you learn from your mistakes, he’s brilliant. Write to him at [email protected] . He's away from the advice desk this week, so he's chosen some of his favorite letters from previous columns to share.
Related Slideshow: 10 New England Wine Getaways
Hardwick Vineyard & Winery
Central Mass’s own Hardwick Vineyard & Winery, open March-December, is a close to home treasure that produces 3,000 gallons of wine each year. The winery, which grows 6 varieties of grapes, is built on a quiet road in Hardwick that abuts the Quabbin Reservoir. Located on the property is a majestic 200 year old mansion. This weekend, take the trip to the vineyard to enjoy a wine tasting. Favorites include Massetts Cranberry and Yankee Girl Blush. If you head out on a Sunday; you’ll be in luck—the winery is hosting Sangria Sundays for the rest of the month.
3305 Greenwich Road, Hardwick, MA. (413) 967-7763.
Westport Rivers Vineyard & Winery
Tucked away on the southern coast of Massachusetts, Westport Rivers Vineyard & Winery, located about an hour’s drive from Worcester, is worth the trip. For only $10, you can take home a special edition etched wine glass and enjoy a tasting of up to six of their award-winning wines. While the tasting room is open Monday-Saturday, free winery tours are also offered to the public every Saturday from 1-3pm.
417 Hixbridge Rd, Westport, MA. (508) 636-3423.
A relatively young addition to the Massachusetts family of wineries and vineyards, Coastal Vineyards in South Dartmouth opened its doors in 2004. Coastal Vineyards grows eight varieties of grapes on their property, including Riesling, Merlot, Pinot Noir, and more. For a special treat, head over on Sunday for their Ugly Sweater Wine Party featuring acoustic musician Ryan Thaxter. Don your ugliest sweater to get 35% off your purchase—and a chance at a prize.
61 Pardon Hill Road, South Dartmouth, MA.
Amherst Farm Winery
Head out to one of Massachusetts’s favorite college towns this weekend to check out Amherst Farm Winery. Enjoy a wine tasting set in a cozy 19th century post and beam dairy barn. For only $5 receive a logo glass and a taste of 5 of their 15 wines, including unique flavors like chocolate raspberry, pumpkin frost, cranberry, and more. Bring a picnic and cozy up on their leather sofa by the fire to enjoy your wine with a snack.
529 Belchertown Road, Amherst, MA. (413) 253-1400.
Nashoba Valley WInery
Take the bite off the winter chill this weekend and take a drive to Nashoba Valley Winery in Bolton. The winery hosts tasting events everyday from 10am-4:30pm For $5, receive a free tasting glass and samples of up to five different wines. Some favorites include Strawberry Rhubarb Wine, Holiday Special Cranberry Apple (a new release in November 2013), and New English Cider. If you are in the mood for something other than wine (if that’s possible), check out their beer selection as well!
100 Wattaquadock Hill Road, Bolton, MA. (978) 779-5521.
Mill River Winery
Mill River Winery, located in Rowley, is the perfect wine destination for a mini-getaway. Enjoy the gorgeous winter scenery of Western Massachusetts as you wind through country roads to the winery. Mill River’s tasting room is housed in a refurbished cider mill, complete with eclectic décor that provides for an excellent tasting and shopping experience. Try their delicious Naked Chardonnay, a full bodied chardonnay with aromatic notes of lemon zest and pear. If you would like to get a “Dirt to Bottle Tour,” make sure to be at the winery at 2pm or 4pm Saturday or Sunday.
498 Newburyport Turnpike, Rowley, MA. (978) 432-1280.
Black Birch Vineyard
For only $6, get the full Black Birch Vineyard experience—tasting and a tour! Enjoy the great mix of contemporary and rustic décor of the tasting room and the local culture of this Massachusetts winery. While you’re in, be sure to try their award winning selection of reds and whites.
155 Glendale Road, Southampton, MA. (413) 527-0164.
Taylor Brook Winery
Located just over the border, Taylor Brook Winery in Woodstock, CT, is a hidden gem. This winery tends to over 2,000 vines of the finest grapes in the region. Head down to enjoy the country hospitality of this great local business, which offers tastings, bottles of their wine, and other great gift items for purchase. For a delicious winter wine, try their Winter Pomegranate.
848 Route 171, Woodstock, CT. (860) 974-1263.
Obadiah McIntyre Farm
Obadiah McIntyre Farm Winery
The Obadiah McIntyre Farm Winery is located on the Charlton Orchards Farm property. The winery is owned and operated by a family that has been in the business of growing fruit for over 50 years, and began making wine in 1999. They are dedicated to making the best tasting wines around. Every weekend until the end of December, join them for a tasting and see for yourself.
44 Old Worcester Road, Charlton, MA. (508) 248-7941.
Puttney Mountain Winery
Just over the Vermont border, Putney Mountain Winery located inside Basketville, has been making delicious local wines since the 1990s. All of their wines are crafted from local produce, which makes for the best tasting wine possible. If you’re toting the kids along for the day, the winery also sells juices made from locally grown produce, like their Putney Bubbly Vermont Sparkling Black Currant.
8 Bellows Falls Road, Putney, VT. (802) 387-5925.
- Best of Dear John: Size Matters, Nanny Lust + More
- Dear John: An Affair To Forget
- Dear John: Beach Wear Barely There
- Dear John: Compromising Positions
- Dear John: Dating That’s All in the Family
- Dear John: Do I Really Want An ‘Escort’ For My 26th Birthday?
- Dear John: Friend’s Drunk Boyfriend Gets Kissy
- Dear John: Haunted By Hook-Up At His Kid’s School’s Drop-Off
- Dear John: He’s Old Enough to Be Her Dad
- Dear John: How Will Boyfriend React To Her Diagnosis?
- Dear John: Is Neighbor a Cat Burglar?
- Dear John: Keep Your Pants On
- Dear John: Love Her, Hate Her Rhode Island Accent
- Dear John: Mom’s Friend Is His, Too
- Dear John: My Father-In-Law Is Trying To Date My Friends
- Dear John: No Affair. And Maybe No Friendship.
- Dear John: Pros and Cons
- Dear John: Schoolgirl Crush
- Dear John: Should I Tell My Roommate Her Dad’s a Lech?
- Dear John: Suffering for Art
- Dear John: There’s No Pleasing Her
- Dear John: What’s Wrong With This Picture?
- Dear John: Will Making Her Feel Awful Make Him Feel Better?
- Dear John: “Guys Weekend” Had More Girls, Fewer Clothes
- Dear John: An Ex With an Imagination
- Dear John: Beds Are For Sleeping
- Dear John: Condoms Pose Barrier for Relationship
- Dear John: Daughter’s Nude Photos Not Welcome in Family Album
- Dear John: Does He Have a Secret Life?
- Dear John: Getting Girlfriend’s Son Off the Couch
- Dear John: He Hates It When I Cry
- Dear John: He’s Tolerant. Kind of.
- Dear John: I Like Him. He Likes Porn.
- Dear John: Is She Just Not Good Enough For Him? Is Anyone?
- Dear John: Let Sleeping Cats Lie?
- Dear John: Love When You Least Expect It
- Dear John: Mom’s Outfits Not Fit to Wear Out
- Dear John: My Husband’s Knitting Is Out Of Control
- Dear John: Nosy Coworker Smells Booze
- Dear John: Psychic Warfare
- Dear John: Sex, Lies, and SD Cards
- Dear John: Should She Be His Sugar-Mama?
- Dear John: Swearing Her Love
- Dear John: They’re Opposites, But Will They Attract?
- Dear John: When “I Do” Becomes “I Don’t Anymore”
- Dear John: Will Third Time Be Charm for Cursed Relationship?
- Dear John: A Clean Break With a Messy Past
- Dear John: An Inflexible Girlfriend
- Dear John: Boyfriend’s Sexy Talk A Total Turnoff
- Dear John: Wingmanning is Getting Old
- Dear John: Dear Diary? Not At All.
- Dear John: Downcast Colleague
- Dear John: Getting Pestered to Pose
- Dear John: He Likes to Watch. Us.
- Dear John: Help Wanted
- Dear John: I Think My Boss Is Having An Affair
- Dear John: Is The Problem The Nude Neighbor? Or The Nosy Ones?
- Dear John: Let Sleeping Dogs Lie. And Lying Dogs Sleep.
- Dear John: Love-Hate Relationship
- Dear John: My Best Friend’s Visiting and My Boyfriend Can’t Wait
- Dear John: My Mother-In-Law Is Sex Offender Paranoid
- Dear John: Nothing to Hide. Except That.
- Dear John: Quit Trying To Set Me Up
- Dear John: Sharing Her Mouth With Her Dog
- Dear John: Should She Leave Her Son With Her Boyfriend?
- Dear John: Thankful for Some Advice
- Dear John: This Time, Painkillers Are Causing Pain
- Dear John: When The Only Sex Is Drunk Sex
- Dear John: With His Father Dying, So Are His Chances To Talk
- Dear John: A Distant Boyfriend. Geographically. And Emotionally.
- Dear John: An Unimpressive Affair
- Dear John: Breaking Up Is Hard To Do (Like, Really Hard)
- Dear John: Coveted By The Neighbor’s Husband
- Dear John: Dear Old Obnoxious Dad
- Dear John: Ending An Affair Much Harder Than Starting It
- Dear John: Girlfriend Tired of Second Place
- Dear John: He May Not Like His Ex, But His Mom Still Does
- Dear John: Her Grooming Calls For An Air-Clearing
- Dear John: I’m A 27-Year-Old Virgin
- Dear John: Is Thirteen Too Young For Sexy Underwear?
- Dear John: Like Kissing Your Sister. In-Law.
- Dear John: Lying to Her Face(book)
- Dear John: My Boyfriend Grosses Me Out!
- Dear John: My Neighbor Is A Pervert
- Dear John: Open Minded About Open Marriage
- Dear John: Relationships 101
- Dear John: She Doesn’t Want Him…Until She Can’t Have Him
- Dear John: Should Viagra Make Her Feel Hurt, Happy, or Neither?
- Dear John: The Case of the Disappearing Lover
- Dear John: Three’s a Crowd. Especially In Bed.
- Dear John: When the Bathroom is the Family Room
- Dear John: You Again?!?
- Dear John: A Divorce of Convenience
- Dear John: Another Dad Gave My Son ‘The Talk’ Before I Could
- Dear John: Breaking Up Is Harder Than He Expected
- Dear John: Dad Wants To GPS-Stalk His Teen Daughter
- Dear John: Deathbed Confession Is Good For Whom, Exactly?
- Dear John: Will I Ever Go On a Date?
- Dear John: Going From One Bad Relationship To Another
- Dear John: He Needn’t Lie About Needing Sex