Dear Jewish Fairy Godmother:

Someone I know from temple just tried to fix me up. We have known
one another in adult ed classes and Torah study. I like her in a polite
kind of way. But we are not particularly close friends, and she has
never been to my home socially. I have expressed some opinions
about books or movies in context, but never given her any reason to
think I wanted her to get involved in my personal life. The reality is
that I am a perfectly happy lesbian and she is trying to get me to date
her nephew. He seems like a nice guy but at my advanced age I am
unlike to cross back over the line, I have kept my private life away
from the synagogue, not because I am otherwise closeted but because
I prefer to keep my spirituality separate from my social life. How can I
politely decline her helpfulness?

No, Thanks

 
Dear No, Thanks:

You’re headed in exactly the right direction: a polite and appreciative
refusal. Tell her very simply that you don’t intermingle your social and
spiritual lives but that you are happily involved in a non-live- in
relationship. You don’t wear a ring because you are not legally married
but you are also not interested in dating anyone else at this time. If
you are you will happily let her know. In the meantime you appreciate
that she’s trying to find a good woman for her nephew and you will
inventory your single friends to see if any of them might be interested.
Ask what he’s like and what qualities he’s looking for. Then you can
decide if you want to ask your straight single friends, many of whom
might want to meet a nice Jewish boy, or just report back that they’re
off the market too.

 
Many people do not wish to be out in every aspect of their lives. That’s
a fair position to take. But unless more gays and lesbians become
more visible in more sectors of the broader social context, people will
not realize how many of them they actually know, like, respect, and
accept as neighbors, friends, colleagues, and adult ed classmates. You
certainly have the right to decide to whom and how you want to
disclose your private life, but given the rapid and positive changes our
society is going through, you may find yourself a throwback as
progress continues.

Dear Jewish Fairy Godmother:

I dated someone for several months. It started out as “you two should
be friends” from a mutual acquaintance. Then as we got to know one
another better we realized that while there was an intellectual
connection there was no “heat.” We still go to movies and dinner, talk
and text, but it seems pretty clear that it’s not going to turn into an
emotional relationship. The problem: While we were hanging out I met
one of her friends that I am genuinely attracted to. What’s the
etiquette about asking her out? Do I need to say something to the first
date before I do?

Ready to Switch

 
Dear Ready to Switch

No one likes rejection. And a formal, even if mutual, rejection won’t
feel a whole lot better than an informal one. A lot depends on how
close they are, and whether you hope to stay friends with only one or
with both of them. My gut says that unless you navigate this in a good
way, you will lose access to both. The risk-reward ratio is high, but
unless you have a long list of other potential dates, give it a try.

 
I suggest asking the original datee to coffee and asking, Where do you
think we are going with this? Friends or other? Let her reject you first.
Then agree, saying you value the friendship and want to continue to
develop it. Once she says yes to that, chat about other things for a
while. Then ask how she would feel if you asked her friend out. She
may demur, and may want to discuss this idea with the friend. But
leave it in her hands for a week and see if she gets back to you. A yes
is a green light to try. A no is a chance to back down or say you are
disappointed and see if she relents. Without a clear green light you are
unlikely to prevail, and you will always have her voice at the friend’s
ear. But what’ve you got to lose?

Dear Jewish Fairy Godmother:

Help me with a dating scenario please. A few months ago mutual
friends fixed me up. There was an immediate and mutual sense of
interest between us and lots of history sharing and sense of meeting a
“possible.” Our time together has been mostly long walks, sitting at
home eating and schmoozing, and generally behaving like an old
married couple. This is in marked contrast to a zappy, fall in love
instantly scenario, the kind my friends have threatened to divorce me
if I announce ever again. I really like Leah’s general style and values,
but there’s a complete absence of pheromones. We’ve both said, I like
you as a friend and maybe more. Let’s take our time. But I think my
idea of “going slow” is several gears faster than hers. When does
patience lead to friendship instead of romance? We’re both in our 60’s
if that matters.

Wanting More

 
Dear Wanting More:

In the world of adult dating there are two primary roads. Road one is
more like no time to waste, are you the right one or not, kiss me now
and see if we spark. Road two is characterized by caution born of life
experience, and a desire to be sure the potential partner is worth one’s
commitment and resources. You sound like a number one person
interested in a number two kind of gal.

 
While it’s great that you’re comfortable with one another, I agree that
you might be mismatched romantically. There’s a fine line between
being seen as desirable and being seen as a masher. You need to up
the excitement ante in ways that lend a little more glitter to the
experience and offer a chance to get a least a little physical.
Something as simple as reaching for her hand on a walk or in a movie
would tell you a lot. If she’s happy to touch in small ways you get a
signal; if she’s not, you get different info. A lovely candlelit dinner in a
nice bistro is a great chance to say you’d like to take the relationship
to the next level if she’s interested. But be forewarned: by putting
your interest so directly on the line, you give her the right to say No
thanks, I’d rather just be friends. Timing matters and so does style. If
she’s a slow go-er, you need to dial back your pheromones and
concentrate on a quality hello and good-bye hugs before you move in
for a kiss. A little sweetness can go a long way. Too much can get you
the door.

Dear Jewish Fairy Godmother:

I’m ready not to be single any longer. What advice do you have to help
me not be stupid about making a bad choice again? For the record I
went for “bad boys” a lot of my life and then tried seemingly boring
and reliable guys in the hope that they’d be different. But no go. Just
like the bad boys: my relationships start out good and go downhill
fast. I’m tired of the revolving door and ready settle down.

Hoping for Better

Dear Hoping:

Do you have a list of “must haves” and deal breakers? If your best
friends wrote the list, how would it be different? What matters to you:
Spirituality? Sensuality? Lifestyle? Finances? Communications?
Social/political values? My personal summary: I want someone who
loves my best qualities and tolerates my worst ones with patience and
humor. Yours may be different; but get clear what it is.
Relationships respond to the energy people invest in them. Good
partners can make life much better; bad ones make it feel a lot worse.
Most of us have histories that would be instructive, if we’d examine
them honestly. Have you learned the lessons of your emotional past?
If not, how often will you repeat then before getting things better or
right? This is a great week to take notes on what you do well and
poorly. On what you want and need. On how to make your current or
next relationship better for you and your honey.

 
Here’s some questions to get things flowing: (Good tip: working in “I”
sentences isn’t selfish; it’ll push you to be more honest.) What makes
you happy? What do you offer a partner? What do you need to be satisfied?
How do you invite people closer? Push them away? When do you really
show up? What makes you more elusive or run for the door? Are you
co-dependent, a narcissist, too much either a giver or a taker? How
and why? When are you a drama queen? When too reluctant to speak
your heart? Do you risk true vulnerability? How do you protect
yourself? What do you show others?  What do you hide? Do you love
yourself? Do you feel you deserve to be loved?

Grab some paper and plan to work on this for a while. Once you’re
really clear about how you contribute to the success or failure of your
relationships you’ll have a much better chance at making them last.

Dear Jewish Fairy Godmother:

Everyone I hang out with checks their email when we’re together and
no one thinks twice. We’re sitting at lunch or out for dinner and they
take a quick discreet glance when they hear a chime. I too am a self
confessed email addict. I have a smart phone and I have different
rings for voicemail, texting, gaming, and email. That helps me only
look when I think it is an important text or email So in my normal
world, I know the rules. But I just started dating someone who has a
best friend. He takes her calls whenever we’re together, and he checks
his email roughly every ten minutes. Do I say something or not?

Ding Ding

 
Dear Ding Ding:

Anyone raised in a pre-digital era would be horrified at the blatant
attention that our electonica receives when we’re in the presence of
other humans. But there’s three things going on: more devices, more
people using them, and more reliance on the need for instant
communication. The perceived tyranny of the urgent, even when it’s
not.

 
Given that you’re working out the ground rules of your new
relationship, this is the perfect time to raise it as a conversation
question. Not in an accusing or challenging way, but rather, I’ve
noticed we’re both slaves to the chiming of our phones. Do you want
to set up some “when we look and who we answer for” guidelines or
just do as we please and see if it bugs one of us enough for it to be a
problem? If asked if it’s a problem for you now, you’ll need to decide
how honest to be, and even have some suggestions to float. But if you
say nothing it’s likely to bug you more and more, and the resentment
will flare up in other ways. If, btw, the guy is a doctor on call, or in
some other equivalent role, you might have to be more flexible than
you want. But it’s worth having the convo to see where your values
intersect or bump heads.

Dear Jewish Fairy Godmother:

I’m 55 and I’ve been single for six years. During that time I had one
extended “friends with benefits” scenario that ended when it got too
emotionally messy. We are finally back to friends again. Then two
crushes with highly inappropriate people that backfired and cost me
some emotional health. And one affair with a married guy who claimed
his wife knew that blew up very badly. I’m a year out of the last
scenario and have spent a lot of time working on my emotional issues
and history of bad choices. In fact, my life seems so harmonious and
calm without all the drama of relationships that I have become a little
scared of dating. A friend wants to fix me up with someone she thinks
I’ll click wit, though another fiend knows the guy in question and sees
nothing in common. Do I risk turning my peaceful life upside down
again, or just slide into old age on my own?

Single

 
Dear Single:

Life expectancy suggests you have several decades in front of you.
That’s a long time to be alone if you are in fact the kind of person who
likes to be coupled. Your history suggests you do, though the
demographic tends in America are for increasing numbers of single
households. Many people who have been married for their whole life
find a new freedom in being single. They blossom into a new life after
a late life divorce or widow/widowerhood.

 
My vote: make the call. You’re unlikely to spend the rest of your life as
a hermit, and even if the connection doesn’t turn into something
romantic, no one can have too many friends for movies, dinner,
concerts, etc. And the truth about dating, as a wise person once said,
is that it’s a numbers game. The more people you meet and greet, the
more chances you have to find someone special. In addition, every
one of those people has friends who are also single. So if you conduct
yourself honorably, they may get points from the other people in their
lives if you get passed on to someone else in their social circle. There’s
a world of singles who don’t want to be. While your ambivalence is
understandable, it’s also ready to be tested by scenarios that are more
viable. You say you’ve worked through your issues. Prove it to yourself
by dating other eligible singles and change your patterns.

Dear Jewish Fairy Godmother:

I just got introduced to a friend of a friend. She’s the first person I’ve
met in three years that I would even consider dating seriously. I have
lots of social companions to keep me busy doing things but have given
up dating after too many disastrous attempts with people who make
snap judgments and aren’t looking for depth or duration. I’m looking
for something real, not shallow. Something where there’ s a true
connection between myself and the other person. A relationship in
which I can really be myself and not have to work to impress someone
only to take off a mask again later. I’m a reasonable catch:
professional, adult, self, supporting, decent looking, and kind. But so
many people seem to want a superhero, not a normal guy. How can I
attract her interest without pretending to be who or what I am not.

Hoping

 
Dear Hoping:

There’s an old quote that goes something like this: If you can fake
sincerity you can fake anything. The oroblem is how many people have
learned to do it well, when you’re trying to be sincerely sincere. The
world has become more complex and cynical, and very few people
assume that others are telling the truth about who and what they are,
whether that’s in an online profile or across a dinner date table. That’s
to your disadvantage. But you’ve listed your attributes and I’m certain
that many people who wanted to believe they were real would also
want to date you.

 
As for the friend of the friend, make a point of taking things slowly but
with expressed interest. Choose to spend time in activities that are
varied: dinner where you can talk and harvest one another’s histories,
mixed with trips to museums or movies where you can share mutual
new stimulation. It’s always hard to know if the spark that makes a
romance last will show up or not. You should be able to tell if your lips
are itching to kiss and if she seems to move closer to you. If it goes
too long without something physical you will both lose interest. But if
you come on too fast she might write you off as just another grabby
huckster. Be sure to express your interest in exploring a real
relationship to the mutual friends. Word travels, in this case to your
benefit.

Dear Jewish Fairy Godmother:

I’m feeling the burden of being single. I have friends to socialize with
for a concert or movie, and I am involved in my synagogue so I am
not isolated. But many of my best friends are coupled or partnered
and they seem to prefer to socialize with other dyads. Even though I
see my friends one-on- one, and the gals go out for drinks or dinner,
they make plans as couples and do not think to include me. That’s
even for things like drinking wine and watching DVDs. I am feeling
sorry for myself and lonely and not sure whether to say anything or
not. These are normally the people that I talk to about anything, but I
am feeling more vulnerable than usual.

Single Sarah

 
Dear Single:

If these folks are really your nearest and dearest, don’t be shy about
saying Please include me if the activity allows for it. Yes you will feel
awkward, even with them, when you say it, so over the phone is fine.
They will almost certainly be responsive and invite you for stay-at-
home evenings. It’s less likely that if they’re going out for dinner or
other activities that you’ll be invited, because it’s much rarer to do
such things in odd numbers, unless more folks are the singles. I’m
assuming btw that you’re not secretly lusting after one of their
husbands, which would be cause for a different conversation.

 
I’m not much of a fan of internet dating, primarily because one has to
sift through so many people who are not as advertised. But you do
sound ripe for meeting more datable people. And even if the majority
of the coffee dates you will have turn out to be duds you will
accomplish several objectives: perking up your social life, and
increasing the chances of meeting someone with whom to do more
social activities. You can accomplish the same goals, though it’ll take
much longer, by taking classes, volunteering, and asking people to set
you up. The last has problems of its own. At least a dud of an imatch
is private or a source of shared humor. Rejecting a friend of a friend
takes more finesse.

Dear Jewish Fairy Godmother:

How can I know if someone is flirting with me or just flirty? When we
made plans for me to go over for dinner and a movie, she said, “Bring
your jammies in case it gets late.” She made a pitcher of drinks, put
on sexy music and said, “Dance with me!” She suggested going away
for a weekend to see a concert. She loaned me her copy of 50 Shades
of Gray, an erotic best seller. I am attracted to her but don’t want to
(a) make a fool of myself, (b) ruin a great new friendship, (c) have it
get serious, uncomfortable, or stop. On the other hand, if she’s
interested, I think there’s something here. What’s the etiquette? PS I
am a lesbian and she has said several times very clearly (in public
settings) that she is straight. I don’t want to embarrass myself by
coming on to her but if she were another lesbian I’d think I was
hearing very unambiguous messages.

Could be Had

 
Dear Could be Had:

The etiquette is not that different than in heterosexual situations. Both
parties have to be attracted to one another for something real to
happen. Both have to collaborate on setting the tone of a friendship
and/or relationship. Both have to want it to be friendly, fun, and
fulfilling for the connection to work. But the very clear I am straight
could also be an unambiguous policy statement to you, as in, Yes I like
to dance and play. That’s who I am; so don’t take it too personally.
You don’t say how long this has been going on. One evening of
drinking and flirting can be excused. A pattern is either someone
testing to see how you will respond, or a personality that may be
dangerous for your mental health. If you are into ambiguity and
suffering, you can play along and see what happens. If you want a
safer and happier life, socialize with people who share your
orientation.

Dear Jewish Fairy Godmother:

When and how is the right time to tell an ex who wants to get back
together (has explicitly said, “I’d like to get back together”) that you
are not only not interested but have begun dating someone else? The
new something is very new, very exciting, but may be just a big hot
flash in the pan. That said, I want to give it every chance to succeed,
and that includes allowing some incubation time without prying eyes or
gossip. Last night I had dinner with my ex who asked if I was seeing
anyone. I felt like a liar when I said “Not the way you mean,” but
immediately saw the hope in his eyes and he once again said, “Maybe
we could get back together. “I don’t want to be cruel so I said, “Not
now.” But I know the answer is “Not in this lifetime.” But I do enjoy
the friendship.

Hoping For Better

 
Dear Hoping:

The intersection of truth and discretion is a dangerous place. Lots of
accidents happen for which there’s no insurance, and a deductible
that’s high enough to do lasting damage to many relationships. You
owe yourself the greatest benefit, to give the new relationship a
chance. But you owe your ex the benefit of honesty if you are really
sure you do not want to reconnect. That’s not only common decency
but will allow both of you to move forward. If the friendship really has
legs as a friendship you will find news ways of relating that are not
based on his wishing and hoping and hanging on for you to make a u-
turn.

 
As for the privacy that you want for your new relationship, yes you
also owe that to yourself. But you do need to have a better answer
than a lie. I&'d vote for. I’m just starting to see someone. No I don’t
want to talk about it. My fingers are crossed but it is too new to know
if there’s going to be enough energy to make it a long-run relationship.
Like any pregnancy, after the first three months have past and the
danger of miscarriage is over, I’ll be happy to tell you about the smile
I hope to still have on my face.

Dear Jewish Fairy Godmother:

I thought I had a date. There was someone I was interested in and
attracted to that I met at a speed-dating round-table. We liked each
other well enough to check the right boxes, get each other’s phone
numbers, and agree to get together. The immediate charge was that
we both played bridge, but neither of us had played for several years
or played duplicate, which we said we’d try together. I invited her over
for drinks and to lay out hands, thinking it would be a comfortable
environment in which to get to know one another. But she appeared in
a shlumpy sweater and jeans I would have put in the laundry two days
before. I wasn’t so overdressed as to be embarrassed but it was clear
(at least to me) that this was not the kind of evening I had imagined.
Do I just back away or should I be grateful for finding a bridge
partner?

Mr. Lonelyhearts

 
Dear Mr. Lonelyhearts:

You convinced me: This was not a date for her, and/or her idea of a
casual evening is very, very different from yours. One mismatched
clothing choice feels like too small a sample on which to decide
everything from, unless you had a lousy time the rest of the evening.
Did you have things to talk about? Did you laugh? Did you enjoy the
cards, think well together, or have a good enough time to want to give
her another chance? If the answers to any or all of those questions are
yes, then look for another occasion to spend time together.

 
You can ask her to a concert or movie so that you have a reason to
talk more. If she declines twice, pleading busyness in general or the
iconic killer I need to wash my hair, you’ll totally get the bridge only
message. But if she accepts and you have a good time, she may begin
to see you differently. I wouldn’t counsel anything big or fancy, just a
casual and possibly spontaneous offer to grab a bite and a flick. She
may not turn out to be the love of your life, but you should definitely
preserve the right to play bridge together. If you do have enough in
common to play regularly you’ll also be in an environment where you
might meet other compatible folks.

Dear Jewish Fairy Godmother:

I’ve been with Sarah for three years; we’ve lived together for two.
There’s a ten-year age difference between us but we feel very right for
one another. We share and have lots of fun with the same activities,
from camping to cooking and food preserving. There’s never been a
time when we haven’t been able to get over a problem in a respectful
and communicative way. Her family has a farm and we’ve talked about
moving there and building a house on the property. I want to marry
her. And, as old fashioned as it sounds, I want to get her parents’
permission before I propose. There’s a local jeweler whose work we
both like and I was thinking about commissioning an engagement ring
and then surprising her the next time we go to the farm for a
weekend. But if either she or her parents say no I’ll be up the creek.
How do I do what when?

Wannabe Groom

 
Dear Wannabe:

You sound like the excitable one in the pair. This is the perfect time to
practice patience. Asking her while you’re at the family homestead is a
lovely idea. But I also think you’re piling everything into a couple
hours when you should be thinking more like a couple than a wannabe
groom. Get a promise ring. It can be something nice but also very
simple and inexpensive. It’s a placeholder, something to show her on
bended knee when you propose. Then the two of you can design the
custom ring together. And even get it made in the right size.
Also, old-fashioned is nice, but know that any time you involve others
you run the risk that something goes sideways. Recognize that when
you ask her folks that they may say Yes, they may say It’s all up to
her, or, the worse case, they may decline to answer and then warn her
you’re going to propose so she has time to think it over. It’s not
always a good idea to propose in front of others, because it puts the
prospective bride on the spot. But you make a convincing case that
she’ll say yes.

Dear Jewish Fairy Godmother:

I&'m finally ready to start dating after five years “off the market”. I&'ve
lived through two bad ten-year marriages and after each wished I
could have the last five years of my life back. I waited this time so I
wouldn’t repeat again the same issues I didn&'t resolve the first two
times. I&'m a self-supporting adult, decent looking and generally
considered intelligent, funny, cheerful, and a good person to be
around. But I am not merely rusty with dating but hopelessly out of
my element. Can advise me how to manage everything from
communications to touching. I&'m a 20th century gal in a 21st century
scene.

Ready?

 
Dear Ready?:

The ? at the end of your question is an indication of ambivalence that
may protect you from another bad choice. But it also may keep you so
guarded that you may miss out on a good one. There’s two routes to
go, speed dating and slow dating. The advantage of speed dating is
that you’ll learnt to talk about yourself very simply and efficiently, and
get used to the idea that there’s lots of people out there looking for
people that like them. Unless you are painfully shy it might be a good
place to start with ice-breakers, deal breakers, and getting your feet
wet. Don’t have unrealistic expectations, but expect to get used to
seeing a span of prospective suitors and realizing that virtually
everyone feels as awkward as you do. Look for events based around
whatever demographic you care most about, whether that’s Jewish,
professional, or just random within an age range. Follow all the usual
cautions about not giving out private contact info too soon. Some
people even get a cell with finite minutes dedicated just to their early
dating life.

 
When you do encounter someone you want to date, either through
speed dating or through more traditional means like a fix-up through
friends, the best rule is to start slow. You want a mix of accessibility
and openness but not full disclosure on everything you are or feel
(from political opinions to food allergies) within the first three hours.
Think of it like a job interview. Have some good stories ready about
various aspects of life. Think about favorite books, movies, hobbies
etc. But be careful about criticizing people you know in common, or
assuming a level of familiarity that’s in appropriate too soon. As for
touching, there’s nothing more romantic than some build up and
anticipation, good night kisses and partial intimacy. It’ll add spice and
buy time while you learn the rest of whomever you’re exploring.

Dear Jewish Fairy Godmother:

I’m ready to start dating after six years. I have had two long-term
relationships (one cohabitation and one marriage). It seems I didn’t
learn my lessons from the first one because the issues that drove #2
and me apart were very similar to the first time around. I took the
time to do my emotional homework, and to develop a strong set of
criteria for what I want in a prospective mate. I’ve made what one of
my friends refers to as The List. But I am a little confused about how
closely I should cling to it, especially because I have dated almost not
at all during this time. Should I practice lots of dating to get my feet
wet again, or does that just set me up for Mr. Wrong #3?

One Toe Near the Water

 
Dear One Toe:

I agree that everyone should have a List. For readers who haven’t
made one, here’s some basic variables to be sure you’re clear about
before you seriously commit to dating someone more than a couple of
times: communications styles (both good and after a fight), emotional
accessibility, lifestyle compatibility, values, intellect, financial equity,
humor, spirituality, sensuality, and just generally liking one another.
One very good indicator of whether a potential relationship has good
long-run potential is visceral: Do you feel like yourself, natural and at
ease, when you’re together? At a gut level, are you comfortable being
you, or do you feel like you’re always trying to impress, that you’re
reflexively critical of the person sitting across the table from you? If
you’re more often squelching a response than speaking easily, or don’t
feel heard when you say something, recognize the bad danger signals.
Here are two simplest rules of dating I can offer. Rule number one:
Don’t be with anyone who doesn’t want to be with you. That can
include eliminating people who’re still in love with their ex’s or who
lust for someone else. Rule number two: Don’t be with someone just
because s/he wants to be with you. There’s nothing as unattractive as
desperation, on either side of the dating equation. You’ve waited a
long time to do this right. Grant yourself the luxury of choice, rather
than being charmed or overwhelmed by someone else’s needs. See
where your list and theirs intersect. There’s good folks out there to
meet, but many to be sifted through to find the right connection. Good
luck getting toes two through ten wet.