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A Dating Odyssey
Getting ready for that all-important first date post-divorce.
By Diana Shepherd

Before you even consider dating again, you need to make sure you're past the "walking wounded" stage following your relationship breakdown. Here are some clues to let you know you've arrived:

  • the thought of your ex no longer generates intense feelings of anger, hatred, or grief;
  • you no longer feel the need to talk about him/her ad nauseam to whoever will listen;
  • revenge fantasies just don't excite you anymore;
  • you've noticed that days/weeks/months go by when you don't think of him/her at all.

If you have truly laid your last relationship to rest, congratulations! Assuming you're interested in doing so, you may be ready to dip your toes back into the dating pool. There may be one more crucial obstacle to hurdle first, however: your relationship with yourself.

During and after divorce, your self-esteem can take a real beating --
especially if the split was your ex's idea.

During and after divorce, your self-esteem can take a real beating -- especially if the split was your ex's idea. If you don't think you're a pretty great person with lots to offer the world (at least most of the time: no one can maintain this level of self-confidence and perkiness 24/7), you need to work on rebuilding your self-esteem before you go out in search of a soulmate.

You may have heard that you have to love yourself before others will love you. Although this is a very good idea (for reasons I'll outline below), it isn't, strictly speaking, true. Even if you totally despise yourself, you can always dig up a few poor souls willing to love you -- or at least, start a very unhealthy co-dependent relationship with you. If the sucker you've attracted is a genuinely nice person, you'll end up despising them. "After all," you think, "I am a completely unattractive, useless excuse for a human being. If this person loves me, he/she must be a total idiot. What a loser: choosing someone as awful as me!" The only person you'll fall for is someone willing to treat you as the loathsome pimple you consider yourself to be. And you can imagine how this emotional S&M relationship will go. Don't even go there!

So the first thing to do is to restore your self-confidence to a healthy level. At the same time, you should work on discovering your new, single identity. One of the opportunities offered by divorce is the chance to re-invent yourself: either as the person you were before marriage, or the person you've always wanted to be. You need to find out who you are now before you can start looking for someone to date.

Who are you?

During your marriage, you probably made some accommodations and compromises for the sake of the relationship. Let's say you used to love to dance/race motorcycles/go white-water rafting, but your mate strongly disapproved, so you stopped doing those things. And maybe your mate thought golf was the only game worth playing, so you've been playing golf for the last 10 years. You now need to look at how you choose to spend your time and make new decisions based on your own desires. If your mate was exceptionally controlling, you may no longer even know what you like. So it's time to get to know yourself again.

Pretend that you're a fascinating person that you've just met and would like to get to know better. Ask yourself some questions. Start small, then work up to the big stuff. For instance:

  • Do I prefer the Backstreet Boys or Harry Connick Jr.?
  • What are my feelings about modern art?
  • Would I rather go bowling or mountain-climbing?
  • As a romantic gift, would I prefer a personal love poem and flowers, or diamond earrings?
  • Would I ever consider cosmetic surgery?
  • Do I run regularly -- even if no one's chasing me?
  • Do I really like nouvelle cuisine?
  • Do I prefer salsa dancing to the foxtrot?
  • Would I ever enter a ballroom-dancing competition?
  • How do I feel about parachuting?
  • Would I ever buy a $3 bottle of wine? How about a $100 bottle of wine?
  • Do I prefer John Grisham to James Joyce?
  • What makes me really angry?
  • What makes my heart sing?
  • What's the best thing about me?
  • What's the worst thing about me?
  • Is there anything/anyone I'd die for?
  • What situations do I find intolerable?
  • Do I want children in my life?
  • Do I have deep religious convictions?

Don't edit: just because you've never been parachuting doesn't mean you aren't interested. And don't look to your past relationship for clues: "Well, my ex always said Garth Brooks was our favorite musician, so I guess I like Garth Brooks." It's perfectly OK to like Garth Brooks -- just make sure it's your own choice, not your ex's.

If you do this exercise right -- with affection and a genuine desire to uncover some of those dreams you suppressed during your marriage -- you're sure to learn that you're a pretty darned interesting person. You may find there's a new spring in your step and smile on your face. You won't give people tacit permission to treat you like a doormat because you know you're not a doormat: you're a person who likes bungee jumping, SCUBA diving on the Great Barrier Reef, and you play a damn fine hand of Bridge!

Another interesting side effect of getting to know this fabulous person who's been hiding inside you is that you'll discover you no longer desperately need to find a new romantic partner. You're no longer a blank canvas waiting for someone to come along and paint a beautiful picture -- to make you whole. In other words, you aren't needy.

And when you're not needy, the world's your oyster -- and incidentally, you tend to attract a better class of mate.

A word of warning: not everyone in your life will like the new, self-confident you. Some of them may prefer you remain a spineless doormat. Insist these people start treating you with the respect a fabulous person like you is entitled to, or drop them. Really! You need all the positive reinforcement you can get, so prune those users and misery-makers from your life. Your true friends will think you're marvelous, and they'll be thrilled to see you blossoming. Anyone who isn't happy for you is a waste of space.

Meeting Mr. or Ms. Right

Now that you're emotionally ready to meet your soulmate, you have to find him/her. Here's a hint: he/she probably isn't sitting on your sofa waiting to watch The West Wing with you. So you're going to have to leave your comfort zone and put yourself out there. This doesn't mean you have to start hanging out at singles bars or attending political rallies (unless you like these sorts of activities). Slowly begin to do things you like that will also get you out of the house and meeting new people. Start taking art, dance, cooking, stand-up comedy, or car-repair lessons; take up tennis, golf, rollerblading, or skiing; go to parties -- even if you don't feel like it; volunteer for an animal rescue organization, traveler's aid, or your local hospital. You'll be meeting other people who share your interests, which gives you an easy opener when striking up a conversation.

And when that special someone shows up in your life, try to flirt instead of running screaming for the hills.

How to flirt

Whole books have been written on this topic. My best advice is to lead with your strong points, even during an initial exchange. For instance, if you aren't funny (you know who you are!), don't try to tell jokes. Still, try to keep things light at first: small talk actually puts people at their ease and can open the door to deeper conversations.

Take a clue from your surroundings: if you're standing in a long checkout line, try: "I can't believe this line is so long," or "Doesn't the cashier look like Rosie O'Donnell?" or even "Gosh, it's hot out today!" After a couple of non-threatening exchanges about nothing important, you can try to find some common ground to create a bond between you and the dreamboat. For instance, you could say, "I'm a bit stiff today: I went rollerblading yesterday for the first time. Do you rollerblade?" If the answer is yes, you can talk about rollerblading for a while: where you go, the equipment you use, what you like about it. If he/she says no, then try: "what kinds of sports do you like?" If that goes nowhere, offer a genuine compliment: "That suit looks great on you." He may respond by telling you where he got it, then you can ask a question or make a (positive) comment about the store.

If you are genuinely funny (ask your friends to be honest with you about this), you could opt for an amusing or offbeat opening line. "Do you think that man is actually wearing a body-shaper under that chartreuse turtleneck?" "Excuse me, I was wondering whether you could give me a really killer opening line. I'd really like to impress you." These must be said with a playful glint in your eye. Be prepared that some people will think you're weird if you stray from "traditional" small talk (the weather, for instance), but do you really want to be with someone so conservative? (If the answer's yes, then behave conservatively with this person.)

Body language is an important part of flirting. This includes smiling (but don't try to mimic the Cheshire Cat from Alice in Wonderland) and standing just a little bit closer than you normally would with a stranger. Warning: there's a fine line between showing interest and pushing someone into a flight-or-fight response: don't stand nose-to-nose, and don't back the person into a wall or corner. This is just plain creepy, and will guarantee that your victim will never want to set eyes on you again.

Try mirroring the person's body language: if she leans forward, you lean forward; if he crosses his left leg, you cross your right leg. Again, don't overdo this: your aim is not to mimic the person, but to put him/her at ease.

Here are a few more tips to set you on the path to successful flirtdom:

  • Always try to look your best before engaging in flirting. If your hair is a disaster, you haven't brushed your teeth, or your mascara has run half-way down your face, you're not going to exude the cool self-confidence a successful flirt requires.
  • Offer a genuine compliment. This could be physical -- "You have such beautiful eyes" -- or not -- "You laugh easily. That's a trait I really admire."
  • If you're good at it, tell jokes (make sure they're neither dirty nor disparaging, though).
  • Never brag -- not even if you've just won the Nobel Prize or the Oscar for Best Picture. Nothing demonstrates insecurity better than bragging -- and it's extremely irritating to be on the receiving end of a bragger in full spate.
  • Be fearless. The worst that can happen if you approach that gorgeous creature is that he/she will reject you. Contrary to what you may feel at the time, this will not kill you. The best is that you may succeed in captivating the most interesting person in the room. Isn't that worth a bit of bruised ego?
  • Be interesting. To charm an interesting person, you need to be interesting. So disconnect the TV and get out there. Push your physical and emotional boundaries: whether that means trying skydiving or yoga. Also, reading some great books will help to wake up those sleepy brain cells.
  • Ask for help. Ask a friend who's a great flirt to give you tips and coaching on everything from body language to ice-breakers to how to tell a joke.

The first date

Okay: so one of you has gotten up the nerve to ask the other on a date. Now what?

Again, start with small talk. I don't care how much you hate it: a first date is always somewhat nerve-wracking, and small talk puts people at ease, giving them a chance to regain their balance. Usually, small talk lasts no longer than about five minutes; some people require more time, and some require less in order to relax.

Your next challenge is to find a topic of mutual interest to discuss. This may take a couple of attempts, so don't be discouraged if your first conversational arrow misses the mark. Try hobbies, sports (spectator and participatory), each other, movies, books, and music. Avoid politics, religion, and your ex-spouse. Of course, you're not going to lie about the fact that you're separated or divorced -- just don't give them a two-hour monologue about the breakdown of your relationship. This is enough information for a first date: "I've been divorced for about two years now. It was a friendly divorce, and I wish my ex all the best." This lets your date know that you're over your last relationship, and that they won't find themselves in the middle of a psychodrama involving you and your ex if they get into a relationship with you. Warning: if your date starts spewing hate and vitriol when discussing his/her ex, run for the hills! Do not get involved with this person -- unless you're interested in years of misery and possibly even danger if these two are still locked in a toxic, hate-filled relationship.

So after you've bonded a little over your shared fondness for Bon Jovi, it's time to start offering and asking for a little personal information. Since a woman will normally have a few safety concerns about spending time with a man she doesn't really know, a man should let her know he's "safe" by offering some information about where he works, goes to church, works out, likes to go with his friends for a beer after work, etc. This demonstrates that you a) have a life of your own, and b) are a fairly normal guy with no big secrets (like you're actually married with three kids or that you're currently out on parole).

Don't interrupt (unless to warn of imminent physical danger: "Look out for that runaway piano!"), lecture, or interrogate your date. Ask questions designed to elicit more than one-word answers, but don't make your date feel as though you're interviewing him/her for the position of "next spouse".

Paying a genuine compliment is always a good idea. "You have a lovely smile," "I love dancing with you," or "You look great in that dress" are all good examples. Being overtly sexual is not a good idea on the first date, so refrain from commenting on breasts, butts, etc. even if you find them exceptionally nice. By the way, if someone compliments you, the correct response is: "Thank you! It's so kind of you to say/notice." Don't deflect it -- "I hate my teeth," "What -- this old rag?" or "I have two left feet" are examples of ways not to respond to a compliment. Even if receiving praise makes you feel shy or awkward, deflecting it will make your date feel stupid, hurt, or annoyed.

First Date Dos and Don'ts

  • Do show up on time; tardiness shows a disregard for your date
  • Do observe rules of proper hygiene: dirty hair, unbrushed teeth, and lingering B.O. are turnoffs and very disrespectful
  • Do make your date laugh (hopefully with you rather than at you). Tasteful jokes and comments only, please: no racist, sexist, or dirty jokes
  • Do pay him/her genuine compliments
  • Do listen at least as much as you talk
  • Do make lots of eye contact
  • Do mirror your date's body language
  • Do remember to smile: dating is fun!
  • Don't dress inappropriately. If you're not sure, ask -- it's less embarrassing than showing up wearing jeans when your date is formally attired
  • Don't ramble on about your ex
  • Don't interrogate your date. The object is to have fun while getting to know each other -- not to interview for the position of "my next spouse"
  • Don't brag or lecture
  • Don't fight about who picks up the check
  • Don't lead with your tongue if you're trying to initiate a good-night kiss
  • Don't sleep with someone on your first date.

The end of the evening

It seems ridiculous, but the issue of who picks up the check can turn a great first date into a minor nightmare. We all come to this with different assumptions: some people feel the person who asked for the date should pay; some people feel the man should always pay; some people feel it should be dutch-treat. Unfortunately, if your assumptions are different from your date's, it can generate a huge misunderstanding about your cheapness/chauvinism/outdated values/ego -- whatever you make the act of paying mean.

The best way to avoid this kind of incident is to establish right off the bat what your expectations are. When making the date, say: "I'd love to treat you to dinner. How about Luigi's on Friday night?" If this advice comes too late for you, initiate a short discussion about it during the date. You can make it impersonal by talking about a "friend's" experience: "My friend Sara had a strange experience last week. She was out on a date, and when she offered to pay half, her date became very angry with her: he accused her of thinking he was cheap, or unable to pay. She was just trying to be polite. It's so confusing these days... Do you think she was wrong to offer?" You'll bond a little on the issue of how confusing modern etiquette is, and you'll find out what your date thinks about who should pay.

If your date expresses a strong opinion, try to respect it. If he wants to pay, but she feels a little uncomfortable about it (maybe she makes more money than him, or maybe her ex was so cheap she simply isn't used to being treated), she could say: "Thank you -- that's very kind. I'll treat you the next time." Do not fight with your date, or try to snatch the check out of his/her hands. Be gracious, and make sure you're clear on what the deal is for the next date before you go out.

The next thorny issue: to kiss or not to kiss? Well, that depends a bit on how the date has gone. If you're not interested in repeating the experience, say, "Thank you for the evening," and shake hands. Note: do not say, "I'll call you" if you have no intention of doing so. Just thank the person, and walk away. If it has gone really well, look for clues that your date wants to kiss you. These include:

  • Lingering outside your car or front door
  • Touching your face
  • Taking both your hands and gazing into your eyes
  • Leaning towards you and gazing deeply into your eyes
  • Saying "I'd like to kiss you."

If your date exhibits any of these behaviors, you can offer a kiss on the cheek, or a light kiss on the lips. No tongues, and no hip-grinding! If your date doesn't pull away after the kiss, and you're equally smitten, you can offer another, slightly deeper kiss.

Regarding sex on the first date: unless you're looking for a one-night stand, don't do it. Aside from any other concerns, there are diseases you can catch that will kill you -- and you can't tell whether or not someone is safe by looking at them. Money and social standing is not an indicator that they're disease-free, either. When you sleep with someone, you're also sleeping with all his/her previous sexual partners -- that makes a lot of people in bed with you! You cannot sleep with someone until you've had a frank talk with him/her about sex. If you're too embarrassed to discuss safe sex, you're not ready to have it.

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