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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'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.
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
- As a romantic gift, would I prefer a
personal love poem and flowers, or diamond earrings?
- Would I ever consider cosmetic
- Do I run regularly -- even if no one's
- Do I really like nouvelle cuisine?
- Do I prefer salsa dancing to the
- Would I ever enter a ballroom-dancing
- 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
- 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.
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.
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
- 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.
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
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,
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
- 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
- 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
- Don't lead with your tongue if you're
trying to initiate a good-night kiss
- Don't sleep with someone on your first
The end of
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
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
- Touching your face
- Taking both your hands and gazing into
- Leaning towards you and gazing deeply
into your eyes
- Saying "I'd like to kiss
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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