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@example.com . 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
Carolyn's Sakonnet Vineya
Carolyn’s Sakonnet Vineyards in Little Compton is much more than just a winery—it is a place to get away from the stresses of life and indulge your senses, a place to try new things, a place to focus on you. The vineyard is open every day, and invites you to come for a tasting and tour. Try their Petite Red, Vidal Blanc, and many more of their distinctive wines.
162 W Main Road, Little Compton, RI. (401) 635-8486.
Visit Greenvale Vineyards in Portsmouth to sample their estate grown and produced wine, made in small batches. While at the estate, try seven different wines and keep the wine glass for only $12. While you are tasting, take in the gorgeous views of both the vineyard and river. Besides tasting the wines, Greenvale also invites customers to tour the winery and learn about the history and process of winemaking at the vineyard.
582 Wapping Road, Portsmouth, RI. (401) 847-3777.
Maugle Sierra Vineyards
For a trip to a vineyard that includes much more than just wine, hop over the border to Ledyard, CT, to check out Maugle Sierra Vineyards. The vineyard hosts live music on Fridays and Sundays to compliment your wine tasting experience. Pack a dinner or light fare and enjoy a tasting session in the Sierra Room while you take in the sunset.
825 Colonel Ledyard Highway, Ledyard, CT. (860) 464-2987.
Nickle Creek Vineyards
Nickle Creek Vineyard is a family owned and operated Rhode Island wine treasure. The winery, located in Foster, makes it their mission to handcraft the most unique, high quality wines in the business. All wines are created in small batches, giving them a distinctly unique taste. This weekend, visit their tasting room to try their variety of wines. On your way out, be sure to pick up a bottle of Foster Nights to get you through those chilly New England evenings.
12 King Road, Foster, RI. (401) 369-3694.
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.
Bishop’s Orchards Winery
The wines from Bishop’s Orchards Winery and Farm Market in Guilford, CT, have won over 179 medals since the winery opened in 2005. The tasting room at Bishop’s is open seven days a week year round, so no time is off-limits for wine tasting. Head over on the weekend to enjoy a winery tour pre or post tasting session. While visiting the winery, also be sure to check out the market for fresh baked goodies.
1355 Boston Post Road, Guilford, CT. (203) 453-2338.
Diamond Hill Vineyards
For a cool twist on classic wine labels, look no further than Diamond Hill Vineyard in Cumberland. At Diamond Hill, you can get custom designed wine labels perfect for any occasion. If you’re interested in tasting the wines, visit their elegant tasting room for samples of their high quality wines such as Cranberry Apple, Estate Pinot Noir, or Blackberry.
3145 Diamond Hill Road, Cumberland, RI. (401) 333-2751.
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.
Found on the southern Massachusetts coast about 30 minutes outside of Providence, is Travessia Winery in New Bedford. This micro-winery puts a twist on traditional wine culture with its cool urban flair. Travessia is open for sales and tastings Wednesday-Sunday, and invites customers to come in and enjoy their unique variety of wines.
760 Purchase Street, New Bedford, MA. (774) 929-6534.
- Dear John: A Clean Break With a Messy Past
- Dear John: Advice for Rhode Island
- Dear John: Baccalaureate Bacchanal
- 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: Ending An Affair Much Harder Than Starting It
- Dear John: Getting Girlfriend’s Son Off The Couch
- Dear John: Haunted By A Hook-Up
- Dear John: He’s Not Homophobic; He’s Boring-Phobic
- Dear John: His Girlfriend Wants a Girlfriend, Too
- Dear John: Is He Creepy? Or Just Determined?
- Dear John: It Feels Too Right To Be Wrong
- Dear John: Like Mother, Like Daughter
- Dear John: Lying to Her Face(book)
- Dear John: Mom’s Outfits Not Fit to Wear Out
- Dear John: My Father-In-Law Is Trying To Date My Friends
- Dear John: No Affair. And Maybe No Friendship.
- Dear John: Pro Golfer Wants To Play Her
- Dear John: Roommate Moves In
- Dear John: She Wants Him To Have An Affair
- Dear John: Some Not-So-Straight Talk
- Dear John: The Family Stoned
- Dear John: Ungrateful Birthday Boyfriends
- Dear John: Where Does Generosity End And Mooching Begin?
- Dear John: You Never Forget the First Time. Whether You Want to or Not.
- Dear John: A Colleague Crush
- Dear John: Agreeing To Marry - Disagreeing About Sex
- Dear John: Bad Dad Wants Back Into Their Lives
- Dear John: But I Liked Her First!
- Dear John: Dad’s Dating Reports Are TMI
- Dear John: Depression Leads to Anxiety
- Dear John: Will I Ever Go On a Date?
- Dear John: Getting Pestered to Pose
- 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: His Low Libido Is Bringing Her Down
- Dear John: Is My Dentist Drinking on the Job?
- Dear John: I’ve Changed…Really!
- Dear John: Living – And Loving – On Borrowed Time?
- Dear John: Make Love, Not Noise
- Dear John: My Best Friend’s Girl
- Dear John: My Husband’s Knitting Is Out Of Control
- Dear John: Pros and Cons
- Dear John: Schoolgirl Crush
- Dear John: She’s Not Fit To Be Tied
- Dear John: Sorry, Wrong Number
- Dear John: The Friend Who Knew Too Much
- Dear John: Unwelcome Contact
- Dear John: Why Doesn’t He Know I’m ‘The One’?
- The Best of Dear John 2012
- Dear John: A Distant Boyfriend. Geographically. And Emotionally.
- Dear John: An Affair To Forget
- Dear John: Beach Wear Barely There
- Dear John: Caught Red-Handed. And Red-Faced.
- Dear John: Daddy’s Play Date
- Dear John: Diary of a Wimpy Parent
- Dear John: Ex Boyfriend. Current Boss.
- Dear John: Girl Friend Trumps Best Friend
- Dear John: He Likes to Watch. Us.
- Dear John: He’s Slept With Everyone But Her
- Dear John: How Will Boyfriend React To Her Diagnosis?
- Dear John: Is Neighbor a Cat Burglar?
- Dear John: Just Friends Again???
- Dear John: Looking Not So Good
- Dear John: Manipulating People
- 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: Psychic Warfare
- Dear John: Seeing Baby’s Birth Kills His Sex Drive
- Dear John: Should I Tell My Roommate Her Dad’s a Lech?
- Dear John: Spreading the Word About STDs
- Dear John: The Gynecologist Next Door
- Dear John: Weird Things Men Do When They Think They’re Alone
- Dear John: Will Boyfriend’s Solitary Pleasures Lead To Pain?
- Dear John: A Divorce of Convenience
- Dear John: An Ill-Advised Office Romance (Aren’t They All?)
- Dear John: Beds Are For Sleeping
- Dear John: Cheapskate Dates
- Dear John: Dating Game Turns Into Waiting Game
- Dear John: Did She See What She Thought She Saw?
- Dear John: Ex With an Imagination
- Dear John: Girlfriend Tired of Second Place
- Dear John: He May Not Like His Ex, But His Mom Still Does
- 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: Just Friends? Probably.
- Dear John: Love Her, Hate Her Kids
- Dear John: Marital Aid Is Anything But
- Dear John: My Boyfriend Grosses Me Out!
- Dear John: My Neighbor Is A Pervert
- Dear John: Old Enough to Know Better
- Dear John: Quit Trying To Set Me Up
- Dear John: Sex, Lies, and SD Cards
- Dear John: Should She Be His Sugar-Mama?
- Dear John: Stealing Away
- Dear John: There’s No Pleasing Her
- Dear John: What’s Wrong With This Picture?