You’re healthy, confident, you have a great sense of personal style, you know how to dress, and you have impeccable manners. Why, then, is it so hard to find a mate? I am asked this question all the time, and by the most appealing people of all ages. First of all, have you noticed that there’s no mystery or romance in the world anymore? Women make themselves so available. You can text a woman an emoji of a glass of wine, and she’ll come over, you have sex, and she goes home. It’s the end of Western civilization as far as I can tell. I certainly wouldn’t call that a relationship. I don’t even like to use the term one-night stand. I prefer to say “Southern sleepover.” There’s a very different playbook for people who are interested in having relationships that might last longer than one night. The question is how—and where—do you find a man or a woman who is a keeper?
The night I met Lon, my first husband, we were at a large party in Washington. I remember it vividly. We were introduced by a mutual friend, we were both intrigued by each other, and, being Southern, I managed to project just the right air of availability and reserve. Lon was with a date, but the moment she went to the ladies’ room, he asked for my telephone number. Sure enough, he followed up with a call. I sensibly reached out to other friends who knew him before I agreed to go out on a date, but destiny had spoken. That chance introduction led to marriage.
Actually, a friend introduced me to my second husband, too. Call me old-fashioned, but at a time when everyone is saying “OkCupid,” I think the best way to meet a potential boyfriend or girlfriend is through mutual friends. People are afraid to ask, but there’s no shame in announcing you’re open to meeting someone and you’d like help. If they can think of a prospect, all they have to do is reach out to him or her and say, “I want you to call this person. I think you would enjoy their company.”
When possibilities arise, be adventurous and go out for drinks and dinners. I don’t believe there is just one person in the world for you. Chances are you will be kissing a lot of frogs (metaphorically) before you find your prince. There will be good nights and bad nights. If that exploratory date is not right, don’t waste time: move on.
A friend of mine experienced a terrible gaffe[1] while on a blind date. At the end of the evening, the man suggested that they play the childhood game rock, paper, scissors—essentially, an extended coin toss—for the check. She lost, and he handed her the bill and went off into the night. I wonder if all his dates end in a free meal?
Here’s my personal checklist of what makes a first date a last date. Dump any man (or woman) who…
And this may be a Southern thing, but I’m instantly turned off when a man doesn’t stand up when you enter the room, or hold your chair when you sit.
I’m going to raise hackles[2] here, but I believe that a real gentleman picks up his date and escorts her home at the end of the evening. Of course, women are capable of transporting themselves, and sometimes logic (or geography) dictates that they will do so—for example, if you are meeting a man for the first time and want to keep your address private until you know him a little better. But a man who offers to call for his date and see to it that she gets home safely, even in an Uber, demonstrates interest, consideration, and fine manners.
There are times when both people do everything right and are on their very best behavior, yet there is absolutely no chemistry between them. You know when you are genuinely attracted to someone and feel a connection. I believe in the power of pheromones. We euphemistically refer to sex as the “birds and the bees” for a reason: nature is in control, dictating our emotions. When you don’t feel that spark, always be gracious and kind, but you don’t have to agree to a second date. Finding the best partner is not an easy job. It took me three times to get it right. Fortunately, we live in an age of recycling. If at first you don’t succeed…
And here’s my formula for a winning first date. The problem with young women today is that they don’t know how to be closers—this is how you should behave if you want a date to go well, and it can work for both men and women, actually. You’re not too enthusiastic. You’re pleasant, but you don’t come on too strong because it can be off-putting. Whitney thinks it’s wrong to play games—he’s all for instant “honesty.” But with my many years of experience, I’ve learned some things. You have to get to know people in stages. If you know too much of them right away, all the mystery is gone. Not only that, much of what people divulge shouldn’t be revealed in the first place. There are certain things that you should keep secret. I believe that!
This caveat[3] also applies to how much skin you reveal. I think women should wear something demure on a first date. Keep the décolletage[4] to a minimum. You don’t want a lot of bosom showing, and you don’t want to wear a miniskirt. Instead, pair something ladylike with high heels. I’m telling my age, but I would wear a simple, beautifully cut dress with pearls. I would try to avoid looking like you-know-who, the Whore of Babylon. I asked Carson Kressley, the charming fashion expert, television personality, and author of the new book Does This Book Make My Butt Look Big?, for his thoughts on what to wear when you want to impress a date.
Ask the Expert: Carson Kressley
First dates can be terrifying for a number of reasons. Thankfully, we can turn to Carson Kressley, the Emmy-winning television star and the author of Does This Book Make My Butt Look Big? (among other titles), for the answer to the all-important question both women and men want to ask…
WHAT DO I WEAR?
We have all heard the phrase “dress for success” and Southern women know wearing the right thing at the right time is crucial! Dressing for a date is like dressing for any other event (wedding, job interview, debutante ball) and it should be treated with equal deference! What you wear could change the course of your future forever! One of my favorite quotes from my hero Tom Ford, and I have many, is “dressing well is a form of good manners.” Keep that in mind when dressing for a date. How you present yourself really tells the other person how much you care about and value them. If you are dating someone you really like, it’s worth the effort and just plain good Southern manners to present yourself well. You’ll feel better about yourself too, which ups your confidence level—which is very attractive!
What kind of an image should I project? Truth, fiction, or fantasy?
Clothes have the power to convey all three, so I think it should be a combination of all three! You should project the best possible version of you! If you are a jeans-and-T-shirt kind of gal, why not up the ante a bit and wear dark jeans and a super pretty and feminine top with great shoes and accessories? That way you will be comfortable in a wardrobe that’s very much “you” but amped up for the location.
Is there a formula (in a good way), for the perfect outfit? What do you recommend?
First of all, make sure the clothes are well tailored, clean, and something you are comfortable in. Here’s an easy formula—have the main garment be something you’re comfortable and confident in—not sloppy, though! (This could be a great pair of jeans or a flirty skirt or a sexy dress.) Then add one element that is sexy or flirty. It could be a lacy bra, a pouty red lip, or a sexy heel. Pretty with a cool edge is what you are going for.
Oh, and one last thing: all Southern women know that “only whores and children wear red shoes.” I promise you I did not make this up. Southern legend at its best, and great advice I think.
I’m coming right from work—how can I transition my look from daytime to DATE?
This one’s easy. It’s all about accessories. Simply change the shoes, bag, and earrings! Go from flats to heels or a strappy sandal. Switch out your big “day” bag to a sparkly clutch. Then pop on a statement earring and you’re ready for some rosé and Prince Charming!
Now that you know how to dress properly, what’s the best destination? Go out for cocktails for that first look. I wouldn’t commit to anything beyond that right off the bat. Here are some other tips:
So you made it through cocktails and you’re looking forward to your second encounter—probably a proper dinner date. Again, dress appropriately. And, as you sit at the table, contemplating your menu, remember that how you order is very important the first time you share a meal. Your date doesn’t want to listen to a diva reciting a high-maintenance list of foods she cannot eat, like, “I don’t eat gluten. I don’t eat salt. I don’t eat meat. I’m on the Paleo diet.” Keep your food rules to yourself. All your “don’ts” are boring, and if all goes well, you will have plenty of time to reveal your idiosyncrasies later.
Whitney told me about a funny experience he had on a dinner date. He was out with a model who ordered two California rolls. She proceeded to eat them with a knife and a fork, methodically removing all the rice and pushing it around her plate for the entire meal. He was fascinated and appalled. They did not go out a second time.
When you order, choose something simple and easy to eat—nothing messy, like pasta, or that will require too much attention. A perfect choice would be grilled asparagus, a petit filet, and mashed potatoes. Yes, you can eat potatoes on a date—you won’t go to hell. But you should never order spinach or a salad; that’s a given, because inevitably something green and unattractive will end up between your two front teeth.
If you really want to make an impression, order dessert. I think some women are afraid to admit that they have ever met a sweet, let alone ingested one. But a person who is confident and enjoys life orders a dessert every now and then—or, at the very least, offers to share one.
Now let me give you a little advice about conversation. We do things differently down in Dixie, and everyone can learn from that. In the South, there is a more traditional approach to what to talk about on a date. For example, you don’t discuss money, religion, or politics. Northerners are likely to exchange verbal résumés: they ask what you do, where you live, who you work for, and they even discuss how much things cost. The first time I went to dinner with Arthur’s business partners I was flabbergasted when they started talking about the buying and selling prices of their apartments. That would never happen in the South.
Southern girls don’t really ask, or tell, you everything because they like to retain an air of mystery. They’ll circle around by discussing who your family is, or how many brothers and sisters you have—because they know listening to someone speak can tell you as much about them as what they actually say. Life is not as aggressive down here as it is in places like New York. A date doesn’t have to be an interrogation. Flirting is more important than administering the third degree, and Southern women definitely do that better.
I define flirting as giving all of your attention to the person you are with, using what I call the “Nancy Reagan gaze.” This works on all sexes, by the way. You look at your date with rapt attention, as if every word is a pearl of wisdom. You smile. You laugh. You’re encouraging. You’re impressed. You’re appreciative, even if the conversation is about pig cloning. There are certain warm gestures you can employ to punctuate your conversation. Touching a person’s sleeve, for example, shows that you’re fully engaged and doesn’t come across as being sexual. A few tips from the Southern flirt’s handbook…
Asking questions and letting men talk about themselves usually makes them think they’ve had a wonderful conversation. Is this sexist? No. Maybe a little retro, in an amusing Sex and the Single Girl way. But being attentive is an indication of good manners. And what’s wrong with turning up the wattage and being bright, funny, lively, and having a sense of humor about things? No one wants to be around a sourpuss or a grouch, and I assume no one wants to be one.
When I started to write this book, I took a look at my old, dog-eared copy of Sex and the Single Girl because I recalled that author Helen Gurley Brown offered smart, snappy advice to women in the 1960s. She did, bless her heart—and this time I mean that sincerely! Some of her suggestions seem quaint now because a single, independent woman is not the rara avis[7] she was almost sixty years ago. There are a lot of references to premarital sex (remember that?), capri pants, and “man-snares.” But I like the way she emphasizes the importance of one-on-one contact, or the classic date.
Like Helen, I want to revive the old-fashioned picnic as the best setting for Advanced Dating: a casual, yet captivating followup to exploratory drinks and the first dinner. Think Warren Beatty and Natalie Wood in Splendor in the Grass. What could be more romantic than a basket packed with food that is (or appears to be) homemade? My picnic basket, which I’ve had for ages and is probably considered vintage at this point, was made by Asprey & Sons of London and is outfitted with fine china and silverware. But you can find wonderful alternatives at PicnicTime.com. Their “Romance” basket comes with everything you need, including a corkscrew. Or, if you prefer, you can buy an empty basket and add your own decorative tin plates, plastic stemware that looks like crystal, silverware with wooden handles, and big linen napkins.
For a foolproof menu, include the classics: cold fried chicken, a cheese selection with a baguette, brownies, chilled wine or champagne, or mason jars filled with lemonade. Avoid anything with mayonnaise, because it spoils.
Aside from my many years of personal experience, how do I know so much about finding a partner and maintaining a relationship? These days, one of the ways I stay up to date is by observing the mating rituals of my costars on Southern Charm. Whitney’s in a class by himself because he’s my son, of course. Cameran is happily married to her adorable husband, and Craig is with Naomi. But Landon, Kathryn, Shep, and Thomas are perfect examples of singles who could benefit from my advice. After all, no one wants to end up being a “shameless strumpet.”[8]
Landon, a beautiful young woman inside and out, doesn’t know how beautiful she is. Because her first marriage ended in divorce, she’s a little fearful and uncertain of how to move forward. As I like to tell her, get over the past and move on. When I knew my marriages were over, it was onward and upward, no looking back for me. No man is worth crying over! As trite as it sounds, I always think that things happen for the best—or at least I make them be for the best.
Last season, Landon confessed to Shep that she was in love with him. That didn’t go well. But I applaud her for taking a chance—it may not turn out the way she wants, but it is important to try. I’m also trying to impress upon her how important it is to have a life of her own. Never give the impression that you’re dependent on anyone else for your happiness. People can smell desperation a mile away, and they run away from it. You want a partner, not a Saint Bernard with a keg.
Shep is a darling guy—I love his smile! But I could have told Landon that he’s a classic Peter Pan who is not ready to commit to anyone yet. That’s what makes his social media handle, @relationshep, so funny and ironic. As Landon says, Shep is like “a golden retriever. If another ball comes by he chases it.” You know the type, and if you accept him as he is, you can have a wonderful time. But if you fall for a Shep, better check those expectations about love, commitment, and happily-ever-after at the door.
In my heart, I have a soft spot for Thomas, even though I’ve been pretty hard on him. There’s no question that Thomas has been a bit of a rake[9] with women. Thomas was running for office at the time, and I thought he should be on his best behavior. I told him to think twice about getting entangled with someone whose ambition in life seemed to be to become a baby mama. My words were: “Instead of impregnating twenty-one-year-olds, you might want to refocus, is all I’m suggesting.” He didn’t listen.
This whole “baby mama” thing is alien to me. In my day, if you got knocked up, you went to a home for unwed mothers and your parents changed their name and moved to Missoula. Now you get to star in a reality show.
After hearing about Kathryn and Thomas’s hard-to-believe second pregnancy and witnessing all the crazy drama and discord in their “relationship,” I had to tell Thomas a hard truth. “In all my ancient years here on earth,” I said, “I don’t know anybody who had to have one paternity test, and you’ve had to have two.” He needed an intervention.
What makes smart people turn into dummies when they fall in love? Remember Maya Angelou’s brilliant words: “When people show you who they are, believe them.” Even though love is blind, keep your eyes wide open and pay attention to a potential mate’s words and deeds. I think these considerations are so important. What is his relationship with his parents? Someone who doesn’t speak to his mother, for example, is not a good prospect.
Do you have interests in common? That sounds like a no-brainer, but in the early blush of a relationship, we sometimes forget that our similarities can be more important than our differences. Not to make this too complicated, but the similarities in question should be important ones, not just funny coincidences. When I met my second husband, Ed Fleming, we were amazed to learn that both our mothers were Colonial Dames and that we both loved to eat Spam. Essentially, a shared passion for canned meat was the basis for our marriage a few weeks later!
I’m also amazed by what couples don’t talk about. They may know each other’s preferences for a Starbucks, or a football team, without ever discussing the important subjects that define a serious relationship. Before you even think about making a commitment, these issues must be on the table.
Vital Questions to Ask…
As I’ve said, you have to be a risk taker. But I’m a big believer in taking calculated risks. The odds are against you if you think you can spend the rest of your life with someone without addressing these important questions.
My friend Georgette is a lifelong entrepreneur and CEO of international corporations, a political activist, a philanthropist, and one of the strongest and most successful women I know. She has a remarkable understanding of how to build a vital and enduring relationship, which she outlined in her best-selling book, The Feminine Force: Release the Power Within You to Create the Life You Deserve. I asked her to share her thoughts.
Ask the Expert: Georgette Mosbacher
You stress that being attentive is one of the most important tools in connecting with another person. What’s the best way to communicate interest?
Look people straight in the eye, be a good listener, and sincerely engage.
What are the two questions to ask yourself when you meet someone potentially appealing?
Do they have a good sense of humor, and do they have good manners?
What does it mean to be “game,” and why is it important?
Be openminded, adventuresome, and curious, and those qualities will present opportunities that otherwise would not be so apparent. You will have a better chance of meeting interesting people if you’re a little out of your comfort zone.
Is compromising a sign of defeat or a way to build a successful relationship?
Compromising is never a sign of defeat, unless you’re compromising your values, and then you’re just defeating yourself.
Of course, the relationship I’m most interested in is Whitney’s. I used to go to the trouble of checking out the women he dated to see if they were daughter-in-law material. I hoped for a beautiful girl with a PhD in art history—someone well educated, cultured, and charming. I mean, my mother required my beaux to be in the Social Register. Now, I’ve shortened the list of requirements for Whitney’s dream girl: I’ll settle for anyone who walks upright.
That’s a bit of an exaggeration. Whitney has had some lovely young women (and I mean lovely) in his life—although there have been several dubious choices. There was the Russian oligarch’s daughter who arrived at the house with twenty suitcases and a puppy. She handed me the dog and made it clear that I had a choice: watch it poop and pee all over the living room or take care of it. Then there was the Latvian model who strolled through the gardens with Whitney, and said, when looking at the pool cover, which had puddles from a recent rainstorm, “That pool is not very deep.” And I’ve saved the best for last: the clueless model who walked into the house, admired my paintings, and then very earnestly announced that her favorite artist was “Moët!”
I try not to be too judgmental (emphasis on try), or put too much pressure on my son, although every parent wants his or her child to be in a committed relationship with the right person. Whitney has been enjoying a smorgasbord of women, but I’m sensing that he may be ready for the main course.
Whenever Whitney decides to settle down, I have four engagement rings from my past—and my mother’s—so he can take his pick. You can never have too many engagement rings. I would like him to get married. Almost all of my friends have grandchildren. I’m still waiting, but what I’ve done in the meantime is adopt a lot of pets.
I’ve been married three times, so I feel uniquely qualified to give advice about romance to Whitney—and to anyone else who will listen. To me, in order to get the life you want, you have to take chances and be open to change. I ended up with Arthur, the love of my life, when I took a leap and accepted his sudden invitation to move to New York. You may suffer a broken heart or two (or three) along the way. But whenever a relationship doesn’t work out, try again. My motto is “Eat, drink, and remarry”—and it has served me well!
[1] Gaffe: a mistake made in a social situation.
[2] Hackles: erectile hairs along the back of a dog or other animal that rise when it is angry or alarmed.
[3] Caveat: a warning or proviso of specific stipulations, conditions, or limitations.
[4] Décolletage: a woman’s cleavage as revealed by a low neckline.
[5] Snockered: drunk.
[6] Unctuous: excessively or ingratiatingly flattering.
[7] Rara avis: rare bird, a rare person or thing.
[8] Strumpet: one of Shakespeare’s favorite words to describe a woman of low repute.
[9] Rake: a man, usually an aristocrat, who is charming, witty, sexually irresistible, and morally reckless.