Category Archives: Dating

Ambivalent

Dear Jewish Fairy Godmother:

Can you help me with the “Let’s just be friends.” conversation? It’s not
that I want to end a relationship, but that I don’t want to restart one. I
was in a six-month relationship last year that started with a bang and
ended with a whimper. The details don’t really matter, but we both
concluded that we could have a good long-run friendship but that we
weren’t really in love with one another and that while we were great in
bed, that wasn’t enough to build a strong relationship upon. The
break-up was mutual and has lasted five months. In the interim she
got involved with someone else briefly, that apparently made me look
like a much better prospect. In the interim I have been single, and
reconfirmed that I really like living alone and not being in a
relationship, or at least not being in one with someone with whom I’m
not really in love. We went for dinner and movie yesterday and her
subtext was laden with “Wouldn’t it be nice to get back together, at
least as lovers….” At least a half-dozen times, and more like double
that. I just let them slide off, but I know the conversation will return.
I’m not averse to the idea, but know that it’s not what I really want in
my life, though with her it could be a temporary thing again. What
should I say?

Ambivalent

 

Dear Ambivalent:

Your signing name says it all. Until you know what you want, you
won’t be able to hold a reasonable conversation on the subject of
creating some form of friendship other than dinner and movie biddies.
There’s not point stumbling through a discussion when you aren’t clear
in your own head or heart what you really do want. You seem pretty
clear about what you do not want with her, but that’s not enough to
engage another person in a serious, or even casual, relationship.
If you know you do not want to have a serious relationship, and that
you are not in love with this woman, you should have the courage to
tell her. It’s not an easy thing to say or hear, but honesty beats
exploitation every week of the year. If you do want to have a friends
with benefits relationship, you can say that. But beware the human
heart, not to mention the biology of endorphins and hormones, which
conspire to impact our emotions. It’s the rare person who can be
intimate without becoming more emotionally engaged with their lover.
One of you might be that person, but both being so is highly unlikely. I
see another break-up in your future if this goes sideways. It’s your call
if you want to risk it. Waiting and dating a while seems like a good first
step.

Leave Me Alone

Dear Jewish Fairy Godmother:

I’m single. I’m happy being single. Everyone I know is married and
thinks I should be too. They keep trying to fix me up on dates, inviting
me to dinner parties, tell me success stories about people who married
later in life and died happily ever, reunited with their lost true loves
from high school, etc etc etc etc etc ad nauseum. I did not have a true
love in high school that I have longed for over the years. Instead, I
supported two deadbeats for the better part of thirty years in two
marriages, thankfully both over, though at great cost. I’ve lived
happily alone for the past ten and travelled, gone on vacations, and
generally had a much happier and more fulfilling life. What my friends
do not know is that I have also been in a mutually consenting friends-
with-benefits relationship with a man whose wife is institutionalized
with Alzheimer’s. Because of our social standing we decided it was
nobody’s business but our own. When people say, with sincerity,
“You’d be sooo much happier with companionship….” and then wink at
me, I want to tell them, but I’ve been quiet. Other than saying “I love
my life,” what can I do?

Leave Me Alone

 
Dear Leave Me Alone:

You’re on the right track with re-inventing your life after two bad
marriages. Many women would crawl into bed and pull the covers over
their head and never go out again. The fact that you are both socially
and sexually active, and seem happy and content is a statement about
your good emotional health and ability to make good choices. That it’s
also good for your wallet is just an added bonus.

 
Tell your friends that you have taken a complete inventory of our life,
from fiscal to sexual. Say that you’re happy with every aspect of your
life, except perhaps needing to lose ten pounds, getting someone to do
your weeding, or finding a better brand of toothpaste. You can change
either of those latter two, but make them playful and distracting. Don’t
put the emphasis on sex, but if they come back with a quizzical inquiry
about you being sexually happy, say that while you’re not a prude you
don’t want to compare bedroom notes with anyone. Try to say that
with a straight face. You might practice this little speech in the
morrow, perhaps after a glass or two of wine. But no matter what,
keep smiling like the Mona Lisa. If they guess at why, you can still
keep mum about whom. And if life changes down the line, they can
dance at your next wedding or just be happy for you.

Once Bitten

Dear Jewish Fairy Godmother:

I dated someone for six months last year. It ended with a whimper
after I had surgery, and my desire for intimacy went to zero. He was a
good friend during my recovery process, but made it very clear that he
no longer considered us to be dating after the second month when I
didn’t want to cuddle or kiss. He very quickly got involved with a
woman that his ex-wife introduced him to (and apparently liked a lot
more for than she did me, as she always seemed quite hostile when
we were dating). But when I bumped into him at the market two days
ago, the first thing he said after “Hello!” Was, “I’m single again. Do
you want to get dinner and a movie on Saturday?” I accepted, but I’m
not sure if I should have added, “But only as a friend, nothing more.”
In fact I think he’s a nice enough guy to spend an evening with, but
he’s proven to me that he cares more about having a girlfriend than
being a good partner.

Once Bitten

 
Dear Once Bitten:

Having dinner and seeing a movie does not a relationship reunion
make. If he’s been a decent friend, then treat him as one, and assume
that his interest is that of a single person looking for companionship,
not automatically a hookup. If he asks you explicitly if you have ever
or would ever reconsider rekindling your relationship, you can answer
truthfully. But in the absence of that question, you should assume that
his news about being single is just that, news, not an invitation to get
back together.

 
If he does ask, and you do decline, he may ask why not. Then you can
choose to be diplomatic or brutally honest. If you value the friendship,
I’d counsel some form of discretion, and an answer that lands
somewhere near I think we are better as friends. Truth is he may
vanish again once he meets the next willing gal.

Too Picky?

Dear Jewish Fairy Godmother:

Is there ever a good way to break up with someone? We’ve been
dating for six months and there is absolutely nothing wrong with this
guy. He’s funny, smart, kind, considerate, financially independent, and
good in bed. On paper, he is exactly what I have said I am looking for
in a new partner, and certainly far ahead of the curve on either of my
previous mates or the guys I have dated between and since them.
What’s the problem? I’m bored. I know it’s not a fancy or dramatic
reason to want to end a relationship. But after six months I feel like
we’ve been together for six years, and I mean six years non-stop
locked a room and can’t breathe. The conversations are flat, the
stories repetitive, and any of “the incredible lightness of being” that I
have felt before when I fell in love with someone seems not just
elusive but remote. There’s no sense of yearning, no sense of
excitement, and the old-robe- and-slippers familiarity is stifling. If I feel
that now, what would happen in a year or four? I’m not getting any
younger and can’t afford to waste too long with the wrong guy.

Too Picky?

 
Dear Too Picky:

You left out loyal and kind from your list of descriptors. There are
hundreds of women who would race a moving train to be in your
situation. And while I am empathetic at your longing for the romantic
ideal, most lives are lived at a simpler, and yes often boring, pace.
Embrace the relationship for what it is: solid and reliable. Suggest that
you surprise one another with alternating responsibility for surprise
adventures. Enroll in a tango class. Or a cooking class. Or lean to play
an instrument or foreign language together. Commit to a volunteer
effort where you will assist those whose lives make yours look like
paradise. And if you are really ready to toss away a safe but boring
relationship, tell your honey you want to date other people. But please
don’t write me six months from now and tell me there are no good
people to date.

Single Again

Dear Jewish Fairy Godmother:

What’s an appropriate birthday gift for someone you have been dating
for two months? I like this woman and can imagine continuing the date
her. But I’m not in love or even committed to dating only her. Her
birthday is two weeks away. She just handed me a flyer for a special
foodie event: a seven-course dinner with wine pairings, at $80 a
person! I was planning on getting her a gift and taking her out for
dinner, but not for $200. What’s a polite way to decline but not make
her think I don’t like her? I should add that my ex always said I was
cheap, but I think I am pragmatic about money, not a spendthrift.

Single Again

 
Dear Single Again:

I think you politely say, Gee that looks like a wonderful thing to do
with one of your foodie friends. I had other plans in mind. Then you
follow through with a gift and a nice meal. And you continue to date
her, and whomever else you want. If this is a way to ascertain what
values you share (or don’t) around money, hooray for a quick and
cheap way to find out.

Not a Fan(atic)

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.

Small World

Dear Jewish Fairy Godmother:

I have two friends that I’ve known for a long time, though far better in
the past decade when we have all been single. We are social for
movies and theatre in dyads, but do birthday brunches with a fourth
friend who is in a long-term relationship. It’s a very small community
of Jewish lesbians, and everyone knows everyone else’s business, was
once with someone that everyone else knows, has heard about every
detail of your personal life (accurately or not), and is incestuous (not
in the literal sexual sense) but with the clannishness of any college
town with a community of migrants from NYC etc. The fourth woman,
Marsha, is not Jewish and has a wider social circle.

 

Complicated social engineering made simple:
Marsha is friends with Jane who converted to Judaism because she was
in a long-term relationship with Sarah, who left her for Ellen, but they split
up and Sarah just moved here. Jane and Marsha agreed I was the most likely
fit with Sarah and connected us and indeed it looks like it will indeed be fun
to get to know her better. But now the other two friends are angry with Marsha
for not picking them, and with me for being less available. To make it
worse my birthday is in May and I don’t want to be social with people
who are angry with me.

Small World

 
Dear Small World:

Friendship among singles and dating in a small pool of people is a
strangely collaborative and competitive world. You want your friends
to be there for you when you have great news to share and also to
help pick you up when romance falters, as too often it does. What’s
most important is to communicate well with your friends, and to do so
with such a sense of happiness and optimism that they would have to
be real grinches to fail to be joyous for you.

 
Go ahead and make your birthday brunch plans. Be sure to talk about
your new romance only part of the time, and try to avoid any air of
relief about no longer being single. Be sure to ask about what’s going
on in each of your friends’ lives and to display the same enthusiasm
for their joys that you would like them to show for yours. Do not,
repeat NOT, invite the new girlfriend to join the foursome “so that
people can get to know her.” Also, be clear for yourself that if she is
new to town she will likely want to make other new friends and
perhaps to date people other than you (including possibly your friends
or your own ex’s). Unless you say you’re exclusive, you’re just at the
front of the line.

Excited But Cautious

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.

No Trump

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.

Confused

Dear Jewish Fairy Godmother:

I’ve been widowed for seven years. You can imagine the number of
well-meaning friends who tried to set me up long before I was finished
grieving my beloved wife of twenty-seven years. Recently, after trying
a fix-up or two with the last remaining single women in this social
circle, I went on the Internet to a nice Jewish dating site. I emailed
back and forth with various women. They were nice but boring and not
nearly as active or interested in travel as I am. Then I met someone I
genuinely like. She’s a year older than I am but she her profile was
great, and when we met for dinner the conversation and stories flowed
like wine. She is funny, articulate, smart, and seemed like just the
independent soul I would like to explore the world with.

 

Here’s the hitch: On our third date she told me of her youngest child
(no mention before this), who had severe brain damage at birth (now
mentally about six though almost forty) and needs 24/7 care, provided
primarily by my date, though occasionally by other relatives or paid
caretakers. She made a point of telling me that she has travelled with
this daughter in various countries, how “independent” she is, and that
it has never been a problem. Maybe not for her! Am I a churlish SOB
for not wanting to take this on as part of my retirement? Of the “many
fish in the sea” this is the nicest catch yet. But I can feel a hook my
cheek as well.

Confused

 
Dear Confused:

Everyone has a different life path that they walk. This woman has
clearly not buckled under a burden that other people might find
crippling. That is to her credit. Though I might understand why she
might be gun-shy about not mentioning this daughter until her third
date, it also speaks to a selective honesty and a different way of
looking that the world that you are right to be cautious about.
I’d reply with a simple email, after waiting a few days. In it ask her
very simply whether she assumes that you would be travelling with
her daughter if the two of you get into a deeper friendship or a
romantic relationship. That’s really the only question. Because if she
says No, you will still need to face the issue if you proceed. And if she
says Yes, you can face it now. I see it as a choice for you, not a
judgment about your character if you decline to take on an adult
disabled child. Other people might. You do not have to be one of them.

Not For Me!!

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.

Roped In

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.

Trying Love Again

Dear Jewish Fairy Godmother:

I had a fight with my best friend. It was over something stupid,
ironically, me defending my ex, about whom I had very little good to
say after the first two years of our marriage, mostly to my friend. I
just started dating someone new, and my friend started with
comparisons, in part to make the point that I was about to repeat
some of the most painful and expensive parts of my past relationship.
To her credit, she’s trying to save me from falling to the same abyss of
supporting someone with a strong sense of entitlement and a
minimalist sense of responsibility. But I don’t want to be treated like
a child or have my newfound happiness invalidated.

Trying Love Again

 
Dear Trying:

Any friend who has suffered the litanies of complaints that most of
us impose on our intimate circle before a break-up has earned some
chits. Often we are too close to a situation—especially in a new
romantic entanglement—to hear what we are saying. Our friends, who
serve as memory repositories for all the mistakes of our lives we hope
not to repeat, are the perfect people to hold up a mirror for us and
say, Remember what you said you’d never do again?

 
That said, you’re entitled to enjoy happiness before reality sets in. If
you are truly acting like an adult, you will be communicating to your
new love the dealmakers and deal breakers of your romantic life.
Kissing and cuddling is fine. But if you don’t respect the person you
wake up with, either because you need to financially support them
from day one or because they are disrespectful of whom you are as a
person, you are better off cutting your losses sooner than later. Call
your friend to say, I’m ready to talk. Then take some time together to
really listen, followed by some journaling about what mistakes you set
an intention not to repeat. If you find your new relationship getting to
close to those lines, start some straight talk with the new love, and
make clear what will end the relationship. I hope you are more right
than your friend.

Out of Shape

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.

New At This

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.