Dear Jewish Fairy Godmother:

I’m in a marvelous new relationship. My sweetie and I have great fun
together, and many of the same hobbies. When we connected in
spring he told me that he was a football fan. Now, no matter what I
suggest that we plan to do or buy tickets for, he says “I’m not sure if I
am going to be free, and I won’t know until the networks decide on
game time.” We have clarified that his blackout times are not every
Monday and Thursday nights and all day/night on Saturday/Sunday,
but rather limited to his alma mater, which is also the local team in
our college town. They mostly play on Saturdays, but are now good
enough that the timing changes from morning to night depending on
the week, and often just days before the game. I find it somewhat
disconcerting to come in second to a televised sporting event,
especially one that could be taped and watched much more efficiently
without commercials. He says the fun is in the suspense of watching it
live, and doesn’t want to risk knowing what happened. The one thing I
do know is that this town is like a morgue when they lose and a party
when they win. I’ve even seen people sneaking peeks at game updates
in services. Oy!

Not a Fan(atic)

 
Dear Not A Fan(atic):

You love the relationship and your sweetie. But you have the right to
be able to make plans for a weekend without worrying about the TV,
the team, or your sweetie’s preference for a pig’s skin to your own, at
least between September and December. This is a perfect time to set
boundaries and recalibrate expectations. If it works it will strengthen
the relationship. If it doesn’t, you will know what you are choosing, or
declining.

 
Sit down with a drink and with your calendar, your sweetie, and your
sweetie’s calendar. Have the football schedule on a screen in front of
you. Ask if there are any Saturday games s/he would be willing to
miss, or are sure to be played early enough in the day that you could
plan an evening together. Mark those on both your calendars. Then,
for the weekends that are Saturday blackout dates for your sweetie,
ask when would be a better time to have a date. Friday? Sunday?
Both? Neither? Once those are established and written in both your
calendars, announce that you are now unavailable on the Saturday
evenings where the TV schedule and his team have first dibs. Say you
plan to make other dates with friends, and that you hope the two of
you are getting along well enough after football ends that you’ll go
back to being regular Saturday dates. Say you have no hard feelings,
but you don’t want to have to dance around the TV and team. Unless
you hate football completely, you could offer to join in for beer, chips,
and a particularly hot rivalry gamey. You might find you enjoy it more
than you like.

Dear Jewish Fairy Godmother:

Help!!!!! I met someone and I don’t know what to do. I’m a
68-year- old woman. I have been divorced twice and lived
alone for ten years. Frankly, I’d given up on the idea of ever
meeting anyone I’d want to date regularly, let alone
contemplating something emotionally more powerful. A few
years ago I went (for the first time, after hearing “success
stories”) on the Internet dating sites. But I saw no one and
retreated with my tail between my legs. For whatever
reason after the holidays I decided to sign on again. Last
week, out of nowhere, I got a knock knock hello from
someone who seems to really get who I am. We’ve
exchanged at least fifty emails in the last week and have a
date to meet for lunch, and maybe a movie or a walk on
Saturday. The list of topics that we have touched on ranges
from all the obvious like family, romantic history, and
professional life to spirituality, travel, creativity, books,
movies, health and exercise, and love of the arts. Clearly
there’s a lot going on but I’m so un-used to this I don’t know
what to do.

Excited But Cautious

 
Dear Excited:

This is a wonderful time of year and of life to meet someone.
Congratulations!! I’m going to devote a lot of energy to the
do’s as well as the don’ts because both are important. I
want to validate both your excitement and your caution. It’s
fun to fall in love, but I’m betting you didn’t get to your age
and wisdom, or your divorce history, without making some
mistake along the way. Remembering those will be part of
the exercise.

 
Start with safety tips. Have your first meeting in a public
place. Pick a restaurant you like at a time that will allow you
to linger if you want to. Be sure to tell a friend everything
you know now about this person, from email address to a
picture, and where and when you are meeting. Ask that
friend to call you thirty minutes in with an excuse that would
allow you to leave if you need to flee. Most such meetings
end up being fine, where that can be a so-so one-and- done
to a great first date that leads to more. But the occasional
few are occasions from which you might need a rescue. So
even if you blush and stammer while saying, My friend
needs me. I’m so sorry. Here’s my share of the bill. While
you flee, know you have an out.

 
Most single people have been building a list of what they do
and do not want in their next partner for a very long time:
qualities that Mr. or Ms. Unknown will have as basic part of
their core DNA, lifestyle, and character. The pretty much
standard ones (in an order reflecting any given moment) are
integrity, sensuality, intelligence, spirituality, good
communications, financial stability, and senses of humor,
honor, curiosity, and common sense. A friend one told me
one of hers was “forthright,” which I interpret in part as an
absence of passive aggressive or whiny tendencies. The
ability to disagree and not hold a grudge or desire to prove
one’s point. My own summary is Someone who appreciates
my best qualities and tolerates my worst ones with patience
and humor. (And hopefully agree on which is which.)

 
Take the time now, before Saturday, to very clearly identify
for yourself the deal breakers. For example someone who
wants to move in this month and put a straw in your 401(k),
or who expects you to sign over the lease to your house.
Beep beep alert!! Also remind yourself of the good qualities
you saw in your exes, before they became same. Someone
who likes to do the same kinds of things as you and whose
speed of life is consistent with yours is a good basis for
dating. Most importantly, make sure this new person
respects the life that you have built over the last ten years
and will not encourage you to abandon it or your core group
of friends. Sometime, if you do not already know them,
google traits of abusers and if you see warning signalsmove
quickly away.

 
As you feel comfortable, introduce this person to your best
friends. Think a series of dinner dates, not one big party that
might feel like a group interview. I’m sure you’re going to
talk about this new excitement, but one by one let them
have a crack at him or her. Listen carefully to their
feedback. They’re bound to be protective of you, because
they’ll have to catch you if you fall. But they’re also not deaf
dumb and blind to your happiness and needs. I hope this is
nothing but naches for you, and that even with your eyes
open you can allow yourself to enjoy the process of
discovering and exploring someone as they are discovering
and exploring you.

Dear Jewish Fairy Godmother:

What do I do about a person I met online? I recently discovered online
bridge, an incredible community of people. At any hour of the day or
night there are 10,000 tables going. A woman whom I met asking to
be taken to any open seat complemented my playing. We did well, had
compatible styles and values of fun and fast play, so we began playing
regularly. I liked her enough to give her my cell number, so we have
been able to text to set up games. We also see when the other logs on
because we are ”friends.” Appreciate she is my replacement for my
best friend and partner of many years who died of breast cancer six
months ago. The new woman, call her Barb, was great in the
beginning but the last few weeks she’s been slow on the uptake and I
have had to prompt her with a “P?” when it is her turn to bid or lead.
This now happens a handful of times in an hour of playing. We tell
people we are fast and friendly but lately in addition to lapsing out she
has made bids that have both opponents and me scratching our heads
and generally seems out of it. What should I do?

No Trump
Dear No Trump:

Online friendships are different than in-person ones, but in both cases
there are real people on the other side of the relationship. I suspect
you could change some settings on your computer and cell phone and
she might think you had vanished of the face of the earth. That’s
cowardly and rude. Instead of disappearing into the mists of
cyberspace, be the kind of friend you probably were to your former
partner. Even if there is a medical reason for her lapses, you’re
unlikely to cook her chicken soup or drive her to chemo appointments
the way you would a close friend. But simple courtesy suggests that
you treat her like a real person with real feelings not some imaginary
robot.

 
Send her a simple text that says, Are you okay? The last few weeks
you have seemed slower and distracted than when we met. I am
uncomfortable telling opponents we are fast and then not playing that
way. I also feel weird prompting you. Please tell me if there’s
something that explains it or how we can get back on track. Wait for a
while before you reply. If it’s temporary accept the inevitable apology.
If it persists, tell her you want to diversify your partner base. The
cyber world has both limitations and advantages. Distance is a double-
edged sword.

Dear Jewish Fairy Godmother:

My question is pretty simple: Is it okay to try and date someone whom
you know is already in a relationship? I recently went to a Halloween
party. I know that Halloween is a time when people are not showing
their real selves, as in their I-am- an-accountant- M/F-9/5, but instead
dress up in some kind of alter ego version of who they might be in a
different or fantasy life. Many of the people at this party had elaborate
rented costumes. I went for the Middle-eastern mystery man in black
with a very elaborate facemask, the kind that left only my eyes
exposed. That allowed me to cruise a party where I knew very few
people without feeling like I had to interact in any particular way. I
saw a woman I was very attracted to, but it was clear from the
costume that she and her date were wearing that they were coupled
(think 50 shades of Halloween). But I have a very strong desire to ask
her out. What’s in or out of bounds?

Roped In

 
Dear Roped In:

Assuming you didn’t wander off the street, ask the person who invited
you to the party if s/he knows anything about the woman in question
and her relationship. Short of a ring on her finger or a definitive I’m in
a monogamous relationship and not looking to date other people, I
think you are in all’s fair in love territory. Unless you learn that an
engagement is imminent, do your best to acquire her phone number
and email. If this case I would opt for a soft approach, an email that
starts out I’m the mystery man in black from ____’s Halloween party.
It’s rare for me to approach someone who’s clearly in a relationship,
but I was very drawn to you. Would you consider having dinner with
me sometime? We can be spontaneous or plan ahead. Assume this
invitation is good for a while, though I would hope you would accept
soon.

 
Very few of us are immune to flattery. And a dinner invitation is not
officially a “date” though clearly that’s what you are implying, even
while acknowledging the relationship. Most women will at least file you
in their “options” file; some will accept your invitation, if only to
compare you to their current beau. If she says Yes, hooray. If she
doesn’t answer you will have to decide among dialing, resending the
email, or asking your mutual friend to place a delicate probe. You
could start there and ask about the history and health of the
relationship. If you do and get warned off from doing anything, you
can hide behind It’s too late. But in the meantime, date some single
people. There’s plenty to go around and those who will cheat on their
current beau are also more likely to cheat on you. Stick with folks who
have been single for a while.

Dear Jewish Fairy Godmother:

For years I worked with a guy and we became close friends, listening
to one another’s personal grief and supporting one another during
work stress. We know the ins and outs of each others psyches, and
what each other wants out of life, in his case a divorce and in mine a
new relationship, preferably one as seemingly great as his now six-
month old one. He invited me to a “very small Halloween party, come
in costume, and be prepared to drink some spicy brew!” So I did.
There were six of us there, a couple we both know, he and his
wonderful new sweetie, and someone he “wanted you to meet.” who
turns out to be a new hire at my old firm. The music and games were
all spooky scary get you to jump into one another’s arms, including a
visit to a haunted house followed by more shenanigans in their spooky
backyard. The fix-up was all grabbing hands and clutching. I made my
excuses early and avoided as much as I could. What do I say now?

Not For Me!!

 
Dear Not For Me:

You say Thanks, but No Thanks. It’s important to acknowledge that
your friend tried to give you what he thought was missing from your
life, what you may have asked for during your kvetching and bonding
sessions. But clearly his idea of how to fix what ails you and yours are
very very different. There are some people for whom a drunken hook-
up is a respite from loneliness. But for most folks of a given age, that
kind of behavior went out the window decades ago. What most people
want in courting behavior is not grabby hands and clutching. It is
being admired and appreciated, romanced, and pursued.

 
Sit down with your friend and ask what makes his new relationship
good and exciting. Encourage him to talk, even if it makes you a little
envious or sad. You need to balance those feelings against your future,
and they’ll help you know where to set the bar for dating. Ask him to
go back to the beginning and say what attracted him to his new
partner, and how they built what you think could be a very strong and
promising relationship. Listen. And then say, That’s my hope for
myself as well. I am happy to meet people you think are solid
possibles. But please don’t mistake my desire for relationship as
anything but that. If it’s not good enough for you, assume I won’t
want to play. Good on you for setting the bar where you want it to be
in your life. Don’t sell yourself short or cheaply.

Dear Jewish Fairy Godmother:

I’m 62 and I need dating advice. I have been single for almost ten
years, not for lack of trying. I just don’t seem to meet anyone who
interests me and I think is attractive who feels the same about me. I
just met a potentially lovely person through new mutual friends. They
moved here and had a big housewarming party; many of their friends
from two hours away attended. One was Sarah, whom the wife of the
couple had confided previously, was single and looking. We had a very
brief conversation (tea not coffee) but she didn’t give me any negative
signals. I am going to her hometown for a birthday party very soon.
Should I: Call the mutual friends and see if she said anything about
meeting me? Ask them for her phone number? Look up her number
online? Find her email from the invitation list? Call or write? Ask her
for a date? For tea? And what tone should I take?

Out of Shape

 
Dear Out of Shape:

You sound more like a nervous teenager than a senior citizen. But I
agree, dating doesn’t get any easier with time. I would vote against
putting the mutual friends in the middle. It sets up a bad dynamic
early in the potential; relationship. If you do end up going out, they
will find out soon enough. If you ask her out and she accepts, you can
happily tell them after the fact.

 
I vote for a simple email. Hopefully you can find hers without having to
ask. Try to write the way you’d talk, simply and accessibly: [Name] –
Nice to have met you. It would be great to continue our conversation
(or start a new one). Coincidentally, I&'m coming to [town] this
weekend for a friend&'s birthday party, and then visiting other friends.
Let me know if you&'d be up for a teahouse connect, and when would
work for you. I&'d enjoy it – hope you would too. You can find me on
email or phone #. Give her a few days to respond. If you don’t hear
back, do nothing else. The next time you see the mutual friends, tell
them casually that you tried to connect. If there’s a message back you
need to hear, they’ll tell you.

Dear Jewish Fairy Godmother:

I’m a year out of a nasty divorce and ready to date. By finally I mean
post divorce trauma and also my first date ever. My ex and I were
high school sweethearts who were married for thirty years. I have
never had to ask out a stranger and I am really unsure what to do. I
like to go walk on the beach and in the woods, and it seems to me that
a perfect first date would be to do that, and then go grab some food.
It would give me and the date a chance to do a lot of talking, but not
in the intense way of speed dating. My friends have people they’re
ready to fix me up with. Do you have any tips for how to look like a
great catch, assuming I want to get caught?

New At This

 
Dear New At This:

When you make plans, be considerate of your date’s preference. Ask
about locale, distance that would be comfortable, time of day, weather
contingencies, and all the things that can make an outing into nature
more fun than disaster. Equip your car with a set of walking poles and
offer your date one. Put a couple pairs of warm dry socks and some
dry footwear in too, as well as a thermos or two of coffee/tea and
treats for before/after. Bring along some trail mix or energy bars, and
water bottles. Try to look like a considerate host rather than a
paranoid Boy Scout.

 
The hard part of first dates is learning a lot about a person without
sounding like The Grand Inquisitor. Ask leading questions about what
your date likes to do for fun, about food, music, movie, and book
preferences, and work life. Avoid asking about or complaining about
exes, physical ailments, financial crises, or other subjects that will
make either of you seem like a whiney deadbeat loser. Listen carefully
but without jumping to conclusions. Try for a mix of companionable
humor, intelligent conversation, and just enough cool mystery that
your date will want to see more of you. Then hope it’s mutual.

Dear Jewish Fairy Godmother:

When a man of senior age is used to doing things (and not doing
things) in certain ways that don&'t leave a lady feeling special, do you
think he can make some changes for the good of our relationship?  I&'m
giving him a couple of months to think things over while I go on a trip.
My vision is that when I return he will have missed me and come to
value me more. I’m hoping he’ll do such things as (l) call me when he
says he will, and (2) show appreciation for me with little gestures,
including the occasional flowers or small gift when he returns from a
trip, etc. Is this realistic?

Hoping

 
Dear Hoping:

I want to be able to say, Yes, sure, some time away will make the
heart grow fonder. And it may. But it won’t necessarily change your
would-be partner’s romantic tendencies. Some of us are suckers for
hearts and flowers, chocolate and little notes, sweet surprises and
gifts, large or small. Others don’t even appreciate being the recipient,
let alone ever think of being the benefactor. It’s not just a male/female
thing, through the old classic Women are from Venus, Men are from
Mars wasn’t totally off base.

 
I understand your logic and hope with this test. But as much to the
point would be my question to you: Are you missing him? Because if
you are not, or if you want to see if you can “win” by changing him,
you’re playing a lose-lose game. If you are comparing him to an ex or
your own habits, you’ll always be measuring him against a standard
he’s unlikely to meet. Even if, like a young dog, he could learn some
new tricks, my guess is he’ll revert to current behavior much sooner
than you want. Rather than focusing on his flaws and failings, ask
yourself what attracted you to him in the first place. Do those qualities
still make you want to snuggle up to him more than other men you
know? If the answer is yes, try again to communicate what you need
to feel appreciated, with emphasis on his creative spontaneity in

providing it. You could also consider leading by example and hope he
gets the hints. But if those steps feel like too much effort, let the guy
off the hook and start fishing around for a true romantic. Be
forewarned, he may lack some other quality you might feel is a deal
breaker. Charm on the front end doesn’t always translate into depth
on the other. All of that said, I hope you find a honey who’ll spark your
senior years.

Dear Jewish Fairy Godmother:

I met a woman I like at a dinner party of a mutual friend. My assets: I
am mid-fifty’s employed, a decent-looking nice guy with varied
interests. My liabilities: I am not yet divorced and I am 15 years older
than this woman, which our mutual friend says should not be a
problem. She did tell me that Sarah is recently divorced and not yet
ready for a steady. Should I just risk getting shot down and call and
ask her out. Is there a polite way to let her know I am interested
without her feeling put on the spot? I’d like her to say yes now, but I
don’t want her to be embarrassed if she wants to decline. I still want
invitations to the friend’s house to meet her again and maybe other
people. It’s been 30 years since I have dated so I am kind of rusty.

Would Be Suitor

 
Dear Suitor:

Nothing makes a person’s ego inflate more than knowing someone is
interested. That’s especially true if the would be suitor is decent-
looking, employed, and a nice person. But it’s equally true that turning
someone down face-to- face (or even by phone) can be awkward and
stressful.

 
I’d ask your mutual friend for Sarah’s email and snail mail address.
Then send a friendly invitational note that says roughly, I enjoyed
meeting you. I’d like to connect again, perhaps one on one, for any
activity you think might be interesting to do together. My range
includes going out for food and talking, a movie, going for a hike or a
concert, or taking dance lessons. Here’s my contact info. Please let me
know if any of this sounds like fun. By giving her time to think about if
and how she’d like to begin, you’ll be demonstrating your nice-guy-
ness. By including dance lessons in the range you’re demonstrating
interest in something intimate, but not in a sleazy way. A handwritten
note is more personal. But email is more modern and faster,
assuming you don’t land in her spam bin. One cautionary PS – don’t
say anything you wouldn’t want your mutual friend to read. Your note
is very likely going to be shared.

Dear Jewish Fairy Godmother:

I have been online dating for many years. I&'ve noticed a trend
changing over the years. When I first became single back in 2001, I
actually met several very eligible men who were available and
interested in developing a real relationship. I had a few very nice
boyfriends over the years though nothing leading to the altar. Now,
however, not so much. First you have to weed out the crazies, and
those who aren&'t broke or within reasonable age range, which
eliminates roughly 80%.

Once you narrow it down and begin
communicating, the men seem lazy: they just want to chat, texting for
days/weeks/months on end without ever meeting. They complain
about the effort to drive even just 30 minutes to meet, expect women
to act like men, and “courtship” is not in their vocabulary. Once they
meet you, if they ever do, the party’s over, the thrill is gone, and the
men vanish. I am attractive, smart, friendly, in good shape, and very
careful not to come off as overly cynical or crazy. I truly think that
online dating is eroding any chance of real relationships. Perhaps
matchmaking would be a better route, albeit much more expensive.
Or, I&'ll grow old alone, because I truly have exhausted every
possibility. I have a very busy life, in a family-oriented city, and no
real way to meet eligible (single) men. Any ideas?

All Talk, No Action

 
Dear Talk/Action:

You’re not the first woman with this lament, nor the first to face the
dilemma of having a life you like, absence of a relationship
notwithstanding. The most important rule if you really want to find a
partner: keep looking, online and off. As a single/looking friend once
observed, It’s a numbers game. So if the folks only don’t want to meet
after a few texts, say No thanks and move on. If you do choose to
meet, follow smart safety rules about neutral public places, giving
cyber-date’s info to a friend, and having that friend call you 30
minutes in to see if you need rescuing. Park in an easily accessible
safe place.

You could consider speed dating, which is an efficient way to check out
a roomful of folks with five minutes of quickie look-sees. Be sure to tell
everyone you respect and like that you are ready to date, and have a
quick summary of your must haves and deal breakers list ready to
share, with a mix of sincerity and self-knowing humor. Live the life you
want to, including adding in new activities where you might meet
people with similar interests. Do everything you can to be happy living
singly, so you&'ll know what is and is not negotiable if you do meet
anyone with whom a second date would be interesting. Think long run.