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Dear John: I’m A 27-Year-Old Virgin

Tuesday, January 28, 2014


What’s your problem? Write to John at [email protected].

Dear John,

I'm 27 (hitting 28 next month) and as of yet I have never been on anything you could really call a date. I started a lot of things later than most people, which has put me out of sync with a lot of friends and coworkers. I've tried talking to my friends and family on the subject and gotten mountains of completely useless advice, ranging from "just go sleep with the first girl who's willing so you're not so nervous" to "just wait and see—the right girl will come along on her own" and just about every meaningless platitude in between.

Until a few years ago, my biggest issue stemmed from a very low self-esteem and a history of self imposed isolation. More recently, however, I've been doing much better. I'm going back to school and doing very well, I'm living in my own apartment and supporting myself, I try to eat right and look better than I ever have, but I'm still struggling with meeting people and starting a relationship.

I'm starting classes at a new school in a new area in a few weeks, and this seems like a good opportunity to finally leave behind my old hang-ups and move forward. What makes me nervous is that I'm going to be ten years older than the majority of my classmates. I'm also finding that the older I get the more I see late teens and early 20-somethings as kids rather than potential relationships. And all of that is compounded by my anxiety at never having done anything like this before. Having never been in a relationship means I get to go through that obnoxious awkward phase everyone else I know went through back in high school.

Am I doomed to having to exclude my classmates for fear of being "that guy"? Should I be upfront about my lack of experience or keep it to myself and feign competence? If I'm upfront, how do I even begin to explain why I've never even so much as held a girl's hand without sounding like the world's biggest loser?

A Late Bloomer

Dear Late Bloomer,

It sounds like you’ve made some constructive changes in your life, with more to come in the near future. I think the only change you have left to make is in how you’re thinking about this. Or, to be more accurate, how you’re overthinking it.

I’m sure that as a 28-year-old virgin, you must look around and feel like you’re the only one not having sex all the time. Well, you’re not. I really don’t want to add to your meaningless platitude collection, but the best thing you can do for yourself is to stop dwelling on this, stop analyzing it, take your new life as it comes, and see what happens. Desperation will put women off a lot more quickly than inexperience will. (In fact, I don’t think inexperience will put them off at all.) You’ve already decided your classmates will think you’re too old for them, and they’ll seem like kids to you anyway – maybe this will be the case; maybe it won’t; but you haven’t even met any of them yet!

As far as being upfront about your lack of experience, let me tell you something: sex with anyone for the first time is a little awkward. You don’t have to offer any kind of preemptive explanation. Sure, if it seems right at the time, you can reveal that this is all a little new to you, but again, don’t overthink it. Just take it as it comes.

You’re not someone who’s “never even so much as held a girl’s hand.” You’re not “the world’s biggest loser.” You’re just you. Keep an open mind, don’t think so much about all of this, and just put yourself out there and see what happens. And if you would, let me know how it goes. I’m confident it will all be fine.


Dear John,

I have an ongoing disagreement with my husband involving our thirteen-year-old son. He doesn’t like a lot of different foods, and when we go out to a restaurant, he usually ends up ordering one of the most expensive things on the menu. (Steak of one kind or another is one of the only things he likes.) I’m writing now because we were on vacation recently and we went to dinner at a very nice restaurant in a very expensive city. My son wanted to order a $42 filet mignon! To me, this just seems, I don’t know…selfish or something. We don’t have a lot of money to spare and I usually don’t let myself order the most expensive thing, and here he is doing it like it’s no big deal. My husband, on the other hand, couldn’t care less. So am I making too big a deal about this, or do you agree that there’s something unseemly about a kid ordering a meal that ends up costing $50?

Eating Away At Me

Dear Eating Away,

Just my opinion, but I think if you go out to dinner, everyone should feel free to order whatever they feel like having without second thoughts. If it gets too pricey, you should go to a restaurant that’s more within your budget. (This goes for you, too, by the way. If you want to order the most expensive thing on the menu, go for it! It’s a treat.)

It goes without saying that a boy with such expensive taste should be prepared to eat what he orders. One $50 steak that’s mostly still on the plate when the check comes would be the last one he’d order if I were paying. But if he knows what he likes and eats what he orders, I’d let it go and enjoy my meal if I were you.


Dear John,

I’ve been seeing a girl for several months now. She’s great—we have a lot in common, we have a great time together, and it’s all good. Except for the sex, which is kind of boring. (As boring as sex can be, anyway.)

Unfortunately, while this has been going on, I’ve also been seeing (“hooking up with” would be more accurate) an ex-girlfriend just because we’re so great in bed together. My situation with her is the opposite: we don’t get along particularly well, we can hardly have a conversation that doesn’t end in an argument, but the sex is incredible. So we get together once in a while just for that, with no illusions that it is anything more than that.

I know this is wrong and can’t go on. My feelings for my new girlfriend have grown to the point that I realize I have to end it with the ex. But I’m worried—I guess my question is, can a relationship succeed if the sex is so-so at its best? What do you think?

Missing It Already

Dear Missing It Already,

I’m not going to answer your question because I think it’s the wrong question. The one you should be asking is, can a sexually unexciting relationship get better? Had you asked that, I would say, “Yes, definitely.”

First things first: you’re right that you have to end it with the ex. Your new girlfriend deserves an honest commitment, and your relationship with her needs your undivided attention. But your letter makes it sound like you’re giving up before you’ve even tried. You don’t provide many details as to what makes sex with her boring, but whatever it is, you have to be more open with her. And you’re going to have to take the lead. Let her know what you want, and if she doesn’t want to try that, what will she try? Maybe there are some things she’d like you to do, too. Approach this in the spirit of finding out what you both enjoy.

It’s great when we hit it off with someone sexually, but it doesn’t always work that way. In fact, I suspect it usually doesn’t. The two of you may have to work a bit (if you can call it work) to see what makes you both happy, but it’s well worth the effort. And you can’t discount how much better any sex is when it’s with someone you’re really crazy about.


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: February Getaways in New England

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Northeast Kingdom

What better way to celebrate the beauty of winter than to head up north for the week? Simple answer: there is none! Head up to the gorgeous mountains of Vermont’s Northeast Kingdom to enjoy all that the region has to offer. Try out Smuggler’s Notch Resort in Jeffersonville—one of the most well regarded family ski resorts in the entire country. Kids will enjoy full day programs and ski/board lessons, crafted specifically for them. Special needs programs are also available.

When you’re not hitting the slopes, enjoy a factory tour of Ben & Jerry’s flagship store, and even check out the flavor graveyard! And if beer and barbecue is more your style, be sure to check out Prohibition Pig in Waterbury!

Smuggler’s Notch: 4323 Vermont 108 South, Jeffersonville, Vermont. (802) 644-8851.

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Mystic Aquarium

Make the trip to Connecticut for an adult treat at the Mystic Aquarium! On Saturday, February 15, the Saturday before February vacation, the aquarium will be hosting a South African wine dinner. Attendees will enjoy South African wines, hors d’oeuvres, and a 4-course dinner amongst African penguins and other beautiful marine life exhibits.

Later in the week, take the kids back to the Aquarium for a great day trip. Explore the exhibits and learn all about life under and near the sea!

55 Coogan Blvd., Mystic, CT. (860) 572-5955.

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The White Mountains

The mountains of New England are a magical place to be any time of year—but they have a little something extra to offer when they are blanketed with snow. Head up to New Hampshire’s White Mountains region to see the beauty of winter in the mountains for yourself!

If you are traveling to the area with kids, look no farther than Lincoln’s Loon Mountain. Learners always get special savings with Loon’s Learner’s Passport. Even better, on select nights during February vacation week Loon will be hosting Fluorescent Nights, a special opportunity to ski or board after the sun goes down.

60 Loon Mountain Road, Lincoln, NH. (603) 745-8111.

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Cape Cod

While people flock to the beaches of the Cape during the summer months, there is something special about being there off-season. Couples and families alike will enjoy quiet walks on the beach and memories that are made without the noise of thousands of tourists in the background.

What’s more is that it is much cheaper to stay on Cape Cod during the winter. If you want a resort, check out Cape Codder Resort & Spa in Hyannis. There’s an indoor wave pool, a spa, and more at the resort, and its proximity to beaches and shopping makes it super convenient.

1225 Iyannough Road, Hyannis, MA. (855) 861-4370.

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Coastal Maine

The Coastal Maine region is another gem of New England summers, but the truth is that it is also gorgeous during the winter months. Take advantage of off-season rates in towns like Wells and Ogunquit and explore all that the area has to offer.

Take in world-famous scenery as you climb the Marginal Way in Ogunquit, enjoy a fresh hot lobster in Perkin’s Cove, and walk along Well’s Beach for a quiet retreat from the rest of the world.

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Roger Williams Park Zoo

Believe it or not, Providence’s Roger Williams Park Zoo is open 12 months a year! Plan a trip to the Zoo with the little ones to help get rid of some of that pent up energy—and learn something while doing it!

Roger Williams Park Zoo is one of the oldest zoos in the country and is home to a bounty of animals—many of which enjoy the cold. Animals you may see outdoors during the winter include Bald Eagles, Moon Bears, bison, camels, and many others. There is no better time to enjoy the Zoo than February vacation—admission is half priced throughout the month!

1000 Elmwood Avenue, Providence, RI. (401) 941-4998.

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Essex Steam Train

The first weekend of February vacation head to Essex, Connecticut for the adventure of a lifetime. February 15 & 16, Essex Steam Train & Riverboat will be having its annual Eagle Flyer event.

Attendees will take a 2 1/2 hour-long eco-excursion aboard the Eagle Flyer out of Essex Station in Essex...pulled by a vintage diesel train. During the ride, naturalists will share information regarding the Bald Eagle’s migration through the region. Make sure to pack your binoculars so you can spot the majestic creatures in the wild!

1 Railroad Avenue, Essex, CT. (860) 767-0103.

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Jiminy Peak

Head to the Berkshires for a snowy getaway during the week of February vacation. Check out Jiminy Peak in the quaint Western Massachusetts town of Hancock—it’s perfect for families!

Enjoy a day on the slopes, but be sure to leave time to explore all that the Berkshires have to offer as well! Local favorites include the Norman Rockwell Museum, Berkshire Museum, Hancock Shaker Village, and more!

37 Corey Road, Hancock, MA. (413) 738-5500.

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Burlington, VT

For a getaway that will offer the best of shopping, winter sports, culture and food, be sure to check out the Northern Vermont city of Burlington. Nestled against Lake Champlain, Burlington is home to world class colleges, delicious eateries, and a pristine natural setting.

While you’re in the area, there is one place that you should absolutely experience: Church Street. Church Street is a cobblestone street not open to traffic in the heart of the city. It is home to gorgeous little boutiques, warm and inviting restaurants, and a great cultural atmosphere. Other highlights of the area include the waterfront, Dobra Tea, and Higher Ground.

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Block Island

Enjoy a retreat from the rest of the world on Rhode Island’s Block Island! Enjoy the sights and sounds of the island—from calm walks on the beach to sightseeing in the interior region. Bring bicycles to get through town, and be ready to enjoy the beautiful natural setting that will surround you.

Block Island is not home to an amusement park, nor is there a fast food joint in sight. Block Island is a place to go to make your own memories—and have fun doing it!


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