Dating should be fun! If it isn’t, you are doing it wrong. But let’s get real—we date for a reason. And those reasons can vary. Whether it’s to find a new husband, enter into a long-term relationship, or to have a little no strings hanky-panky for a night, we each have a goal in mind when we head out the door. Dating horror stories are to be expected, but these tales shouldn’t be any more than late night fodder with the girls over a bottle of vino. To take the pressure off, I divvy up 26 tips to keep dating in perspective, making it the enjoyable experience it’s meant to be, while helping you come one step closer to closing the deal, whatever your deal may be.
A. Always. Always be on your best behavior. That means being polite, saying thank you, and arriving for your date on time. If your date doesn’t extend the same courtesies to you, it’s best to pass on any further dates. Bad behavior only escalates.
B. Be. Be yourself! You want your date to get to know you—the real you. There’s no sense pretending to be a chef, only to reveal on date five you can barely boil water. You love steak? Don’t pretend you’re a vegan. You’re allergic to dogs? Don’t pet one on the sidewalk. That said, a first date is not a substitute for weekly therapy. Keep your conversation light, and leave your baggage at home. Your problems aren’t you. They are only the situations with which you find yourself coping now, and aren’t defining. Remember, you’re wonderful, even if the situation in which you temporarily find yourself is less than that.
C. Closing. The impression you leave at the end of the date is as, if not more, important as the one you make at the beginning. If you had a nice time, say so! Your date doesn’t know you well, and likely carries the same insecurities you do about whether or not he is liked. If you don’t wish to continue dating, be honest. But be kind, too. Never make someone feel worse than they already may (the sting of rejection is already unpleasant enough). Besides, you never know if your date has a friend in mind that might be just right for you.
D. Don’t dress to kill. Look your best, but don’t appear as an aspiring high maintenance runway model. Dress sexy, but not provocatively. You don’t want to give your date the impression you are looking for more than you are (unless you actually are, and that’s okay, too). Wear age appropriate clothing, and clothes that are comfortable so you can focus on your conversation rather than fussing with a top that slips down to reveal too much cleavage, pants that restrict the circulation in your legs, and shoes that make the walk to your car feel like The Green Mile.
E. Eat Lightly. My father always used to tell me to act like a lady. So I do. That includes not ordering up a storm in a restaurant, and not eating food that will make me feel sick before, during, or after a date. I want to feel good when I’m with my date, and I want to enjoy our time together without feeling as though I’m about to fall into a food coma or heave.
F. Fuhgettaboutit. At least for a while. We all have worries, even the guy you’re dating. Jobs, kids, bills, exes… And the list goes on. But for a couple of hours those issues need to be tabled. Enjoy your time with (hopefully) good company (if not, see letter G), and stay in the moment. No doubt real life will be waiting when that moment is up.
G. Grin and bear it. We have all had that bad date. The one where you show up and the person you meet looks nothing like their online photos, or you quickly realize though your date is nice, he is not the guy for you. Unless you believe you are in imminent danger, try to get through the meeting as quickly but as politely as possible. You could be on the other side of that coin one day. I was on a date with a guy who confessed that on more than one occasion women met with him and within minutes made up an excuse to leave. The dog needed to be walked, or she had to pick up a child. I have never fled a date (yet) even when there have been times I wanted to. What goes around comes around, and I wouldn’t want someone treating me so rudely.
H. Help. Help out by being an active participant. One person shouldn’t shoulder all of the responsibility, whether it is for all of the expense, all of the traveling, or all of the planning. Any good relationship will be a two-way street, so do your portion of the driving. Anything less will put you on the road to nowhere.
I. Imagine. Don’t. Don’t start doing Conan O’Brien’s, If They Mated, in your head about you and your date. Or writing your first name with his on a cocktail napkin, and deciding whether or not to hyphenate your last name with his. You will only set yourself up for disappointment later. Those photos on Conan were always super ugly anyway.
J. Joke. “A frog walked into a bar…” While on a first date a few months back with a guy who was no prince, I was zealously told a joke about a frog 
performing oral sex on a woman. My date even mimicked the eye movements of a frog as he rattled off the punch line (thankfully there were no accompanying tongue gestures). The behavior was off-putting and disrespectful. Only the frog got any action that evening, and I am happy to say it (and my date) lived happily ever after and were never to be heard from again. Keep it clean.
K. Kids. Dating, especially in middle age, means a higher likelihood of navigating around those other littler people in our lives who make getting to destinations on time more challenging and keeping our dates more exacting. Interruptions are often par for the course, as well as last minute changes and cancellations. Planning is key, especially when dealing with children, and it is important to be flexible. However, there is no excuse for no-shows, even when kids are to blame. Such behavior should never be tolerated.
L. Listen. Listen to what your date says. He will tell you who he is during those first few meetings. If he says he’s not looking for something serious, believe him. Remember, the only person you can change is yourself, so don’t take anyone on as a project. You’re an independent contractor, not a general contractor, so stop managing others.
M. Money. When on a date who pays for what? There is so much debate on this topic. Split the check so he expects nothing from you in return? Let him pay? Pick up the tab occasionally? Offer to pay your share? It can all become confusing. I must say the best advice I have ever received came from a friend now married to her second husband who said whatever you do, it should feel natural.
N. Nerves. It’s common to be nervous on a first date, especially if you’re as unseasoned a dater as I was when I first began dating after my separation. Do your best to relax because likely your date has a touch of the jitters, too. No matter how many dates a person has had, meeting someone for the first time can be nerve-racking, especially if there is an immediate attraction.
O. Open-minded. By middle age everyone, including those who have never been married, has a unique story to tell about how they came to be your date. There’s never going to be a perfect picture. Dating in our forties, fifties, and beyond takes more effort than arranging on the fly to meet at the campus center after Psychology class. Careers, children, grandchildren, friends, and social commitments all factor in, and even if romance is not written in the stars, we can always learn from someone else’s life experience.
P. Possessed. Be self-possessed, but don’t act possessed. Behave as the smart, sexy and confident woman you are. You have a lot to offer, but remember everyone is looking for something different, and therefore not necessarily for you. Sometimes it boils down to plain old chemistry, or a lack of it. Your date could be a great match for you on paper or, as my mother always says, has all the checks in the right boxes, but if that spark isn’t there, it’s important to accept it and move on. Refrain from theatrics if a relationship doesn’t develop as you had hoped. Crazy isn’t a great description to wear.
Q. Question. Ask questions but be a conversationalist and not an interviewer. No one likes to be on the receiving end of a Q&A session. Facts that can be found on your driver’s license reveal little about a person, and will do nothing toward bringing you closer together.
R. Read. Prepare for a first date as you would a job interview. You know the basics about each other, but now is the time to strut your stuff. Be interesting! Know what’s going on in the world. Have an opinion and own it. A pretty face may get you in the door, but a smart woman is the one who keeps the guy from walking out that door.
S. Sex. Sex is not a commodity so don’t treat it as one. Don’t count dates, and don’t let your date count dates. Have sex because YOU want to. Be honest about your intentions with your date and with yourself. A couple of years ago, a guy I started seeing invited me to lunch for our third date. As soon as I agreed, he followed up with a text asking if he could bring said lunch to my house. When I explained I wasn’t comfortable having a man I barely know to my home, I didn’t hear from him again until he resurfaced a couple of weeks later, apologizing for his less than chivalrous behavior.
T. Travel. I have yet to meet the man of my dreams sitting in my own backyard. For those using online dating, expand your search radius and expand your horizons. I know many city dwellers that have yet to meet The One, and have widened their search to include areas well outside their densely populated neighborhood. When the chemistry is there, miles suddenly won’t make any difference.
U. Understanding. Be understanding and non-judgmental. People come to where they are in life through their own trial and error. The decisions we make are personal, and we wouldn’t want anyone undermining our choices. Do unto others…
V. Viagra. If I had a nickel for every time a middle-aged man advised me unsolicited that he doesn’t need Viagra I would… have a lot of nickels. Promises of sexual prowess on a first date make me wary, and I can’t help thinking back to high school English when one Lady Macbeth “doth protest too much.”
W. Woman. Be mindful of the woman
you are. Recall your feminine side, and let a man be a man. If your date wanted to spend the evening with the guys he would. Be independent, be smart, but be a goddess, too. We each have that potential inside us, so capture it, enjoy it, and let your date enjoy you.
X. (E)x wife. My husband was unfaithful during our marriage. Admittedly, I am not a fan of his past indiscretion. However, when I speak about him to others, I am fair about why our marriage ended. Regardless of our marital status, he will forever be the father of my children, and in my book that entitles him to respect. When I’m with a man who bashes his ex wife, and who talks about her condescendingly, I take note and heed the red flag he’s waving. No one person is ever at fault in a marriage’s end (except in cases of abuse), and I’m wary of anyone who claims otherwise.
Y. Yes. Say it with sincerity. “Yes, I would love to see you again!” Smile when you do. But only say yes if you want. No one should ever put pressure on you to do anything against your will. Yes means yes, but no still means no. Second thoughts are also allowed. Changing one’s mind is always a woman’s perogative.
Z. Zen. Play it cool even if initially you’re not, especially on a first meeting. At this point there’s no pressure and no expectations, only the presumption of kindness from your partner. So stay grounded because, as we know, the best dates are the ones that don’t feel like dates —the ones where we’re so relaxed and at ease we forget we’re on a date at all and are suddenly living our life. And that’s when the real fun begins.
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