Dear Jewish Fairy Godmother:

I’ve been divorced for two months. We live in a no-fault state but the
sad reality is that both of us were at fault in various ways. We became
used to being unkind to one another, and had retaliatory affairs: I
slept with someone at work and after she found out she did the same.
We said we would forget and try to forget. But there was too much
acrimony. Frankly even living in an apartment is better than the last
two years of tension, because I don’t have to worry the TV is going to
erupt into a frenzy and start yelling at me. But I am starting to get
bored and am ready to date. I’m a mid-40’s nice guy, with a steady
income, decent enough looking, and if you ask anyone other than my
wife, a decent sort of fellow to spend time with, have a drink, and get
to know. Do you have any good tips on starting over?

Ready

 
Dear Ready:

You don’t say how long you have actually been divorced. While the last
phases of a dying relationship are very often filled with acrimony and
emotional pain, they also are not be best places to lay a solid basis for
healing and preparing yourself for your new next life. A new place to
live is a start, and your basic info about yourself makes you seem like
you could be a decent catch eventually (infidelity notwithstanding,
though perhaps you’ve learned the lesson). But “ready” happens with
more than just elapsed time.

 
Some useful things to remember are the importance of cleaning out
emotionally as well as changing your physical reality. That could
include counseling as well as journaling, talking to friends and other
divorced folks (not in the griping, “she done me wrong” way. It also
means taking more alone time than you might think you want. It helps
with reflection and really understanding what you miss about relationship
other than physical intimacy. Make a point of being in varied social situations,
from potential dating meet-up places to classes and dinner parties. Get used
to being around people you do not know. I strongly suggest waiting until you’re
clear who you are becoming before choosing your next partner. If you don’t,
odds are high that you’ll repeat the mistakes of the past.

Dear Jewish Fairy Godmother:

I’m not yet divorced. But my wife relocated 2,500 miles away and we
have not been intimate for years. She has started dating where she
now lives. I’ve been shyer about getting back out there, even though I
am employed and decent looking. I’m on several local volunteer
boards where I saw a woman I’d be at least interested in. She doesn’t
wear a wedding ring. We just got assigned to a subcommittee, along
with some other folks. Should I wait to get to know her better before I
ask her out or should I take this as a sign from the universe that the
time to dial is now?

Still Shy After All These Years

 
Dear Still Shy:

Be forewarned that’s there no dating cliché more well-worn than “My
wife and I are separated…..” But someone whose wife is thousands of
miles away has a decent case to make.

My vote is to catch her after a meeting and say something simple, in
person rather than by phone, text or email. Be casual, as in Would you
like to go get a cup of coffee?“ which has the immediacy of surprise
and casual. Or Would you like to catch a movie sometime?“ which is
potentially more ambiguous and casual; invitational but also betrays
shyness. Or Would you like to go out to dinner sometime?“ which is
more “date-y.” I’d vote for number three and sooner, if only to get you
back in the dating game. The upside is that she is free and says yes,
you can check her out and if it doesn’t feel right, just see her in
meetings. The downside is you might get uncomfortable if she says no.
But it’s early enough that you could switch committees if things go
terribly awry. Some people, btw, don’t wear rings, so if she says
something like, Sure, but I need to alert my husband/boyfriend/partner,
you’ll learn a lot quickly. No time like now. Don’t be surprised btw, if the
other committee members notice.

Dear Jewish Fairy Godmother:

I am 64. I recently reconnected on Face Book with my first true love.
We were a couple in high school and would probably have gotten
married and settled down except my mother broke us up. Insert vivid
fights with her, decades of bad relationships for me, until I finally met
my husband, who reminded me of my first love. We had five good
years until he got cancer. I am widowed; I started dating, meeting no
one satisfactory. Then I re-met and am now in love again with my
numero uno, who lives 1000 miles away. We’ve seen one another,
embraced, and affirmed the connection, but haven’t figured out what
happens next. Unbelievably, my mother is still being a B-word about
him. Is this karma? How can I handle her?

Can’t Believe My Good and Bad Luck

 
Dear Can’t Believe:

Some things never change, including parents’ belief that they know
what&'s best for their kids. But at age 64 you have long earned the
right to decide with whom you are in love. And after bad decades and
cancer you deserve good ones.

 
Next might be a visit by True Love to visit you. You can (re) introduce
him to your family. Prior to that visit have a firm sit down with your
mother. Make it plain that you have had a long and complicated
romantic life both because of and despite her interference. But one
serious intervention is enough. Tell her in no uncertain terms, This is
the guy with whom I am going try and make a relationship, even given
the long distance constraints. It may end up in marriage or in flames,
but that’s my problem and right to figure out, not yours. If she is
smart she will keep her mouth shut and watch from the sidelines. If he
is smart he will greet her with a big hug, and try to disarm her with
charm.

Dear Jewish Fairy Godmother:

I recently ended a 15-year live-in- but-not- married relationship. I
supported my ex, whom I watched decline into a sad and unhappy
spiral of drug use, lack of employment, chronic negativity, and general
avoidance of responsibility for herself. It was a long and very difficult
period of my life. Relocating her out of my home and into a settled
new reality was a long and expensive process that I tried to handle as
compassionately as I could. But now that I am living alone I realize
that I get lonelier than I expected, and also that I need some help with
the small chores she did provide, primarily pet care. A woman I have
just started to befriend is new to town. She is looking for a place to
live and has suggested a roommate relationship in exchange for
chores while she looks for a job. Should I be kind and try to help her
or should I put my guard up and beware?

Not Sure What’s Next

 
Dear Not Sure What’s Next:

Any time one changes a major life circumstance it is wise to take some
time for recovery. You don’t say if “recently” is measured in weeks or
months, but I’m betting it’s not years or you would have a clearer idea
of what to do and be more trustful (or mistrustful) or your instincts.
My advice is to say No thanks and here’s why: You could easily re-
create a very similar circumstance to the one you just got out of.
There might not be the emotional complications of relationship. But
there would be the reality of another adult living with you who does
not have visible means of support. You can solve the pet care problem
by hiring a neighbor kid, buying automatic pet feeders, adding a pet
door and covered run or shelter, or other simple solutions. These are
fixes that’ll ensure your domestic freedom while you readjust to your
new life circumstances.

Tell the potential new roomie that you have promised yourself you will
spend at least two years living alone before you make any changes.
Then look for a good counselor to help you look at your issues.

Dear Jewish Fairy Godmother:

I finally joined match.com after being single (widowed) for five years.
I’d been relying on meeting folks on my own, the fix-up kindness of
friends, and dumb luck. It worked for a while and I met some decent
guys, had some lovely dates, and several short-term relationships.
But I’m in my 60s and time is getting away from me so I see every
month I don’t meet some viable or at least new prospects as time
passing me by. I made contact with someone in a city less than an
hour from here and at least online we seemed to have some things in
common, though he’s nine years younger and more active outdoors.
But when I was relating this to one of my friends (also single) I
realized they might be perfect together because they’re both land-use
attorneys. Is it too weird or possible to accomplish this:

Bait and Switch

 
Dear Bait and Switch:

Send an email to suggest the idea. But be sure to keep yourself as
part of the equation, in part to legitimize the suggestion and because
you never know whether you or your friend (or neither) will be a
better fit with the current prospect. Try this:

Hi – I’m still interested in connecting for in-person hello, but this email
has a twist. I had dinner last night with a friend/neighbor named
_____ ________ and as I was updating her on my exploratory
adventures with online dating I realized that you and she might make
a great combo. She&'s very smart (education), very cute (see attached
jpg), closer to your age (___), I also practices land-use law, very
funny/bright, interested in books and movies, and much more physical
than I am. She hasn&'t done the cyber-hello process and I suggested
that I could just shoot you an email with her contact info and you
could decide if you wanted to get to know her better. From what little
you and I have exchanged, and my gut instincts, I think it would be a
good connection for both of you. Her email is _______@xyz.com. So if
a two-fer is bait enough to visit,. I can offer food/drink, because I&'m
still open to meeting. And you can connect with _____ and see if
there&'s a match. My gut says yes. Then see what happens.

Dear Jewish Fairy Godmother:

I’m young and yes occasionally stupid. I ran with a party crowd in
college but now am living more simply. I have a good job and was in a
five-year relationship but realized it was too confining.. Two of the
friends from my old crowd got married last weekend, My ex showed up
at the wedding and I got totally flustered. I decided to get hammered,
which was the first time in forever that I remember being that drunk. I
ended up spending the night (and yes having sex) with a friend who
seemed just fine when I was drunk but I do NOT want to get more
involved with. He’s already texted me three times and wants to get
together again this weekend. Is there a polite way of saying that I
want things to go back to the way they were? I like him fine as a
friend, but he’s still into partying and I’m not that kind of girl any
more.

Ooops

 
Dear Ooops:

It’s not surprising that he assumes you haven’t changed because
nothing that you have said in your question would indicate that you
have, other than that you have a job. In his mind you are ready to get
drunk and go home with him. Of course he’s dialing for more. Words
are one thing to use, but actions speak much more loudly. You can
follow the advice below, but if you backtrack and end up in bed with
him again, he’s not going to believe you when you say No thanks a
second time.

 
In the olden days, when I was young and dating, we would have said,
Boy was I drunk last night! That didn’t excuse our behaviors but it did
imply that we were not planning to continue them as a regular
practice. Best would be to thank him for a lovely evening, but say you
don’t want to repeat it, soon or ever. Explain that after a decent
interval has passed you might be interested in dinner and a movie with
him, but you aren’t planning on drinking too much and sleeping with
him again. Friendship is all you want. Then make that true.

Dear Jewish Fairy Godmother:

A fix-up/new friend and I were checking each other out for a few
months. It started out gangbusters, lots to talk about, chatter chatter
chatter. Then she went away on a trip. When she got back it took a
month or so to find our sea legs again, but I figured, hey, she’s been
gone and it takes time. We went out on a few dates and it was all very
proper, though we did mutually agree that we were attracted to one
another, just not in any rush to jump into anything, bed included.

As the months went on the desire to see one another seemed to wane,
but frankly there’s simply no one around I am even remotely
interested in and I have never and don’t think I would ever be willing
to do internet dating. Lately all the conversation has been around her
hassles at work, dreams of retirement, and gardening. Yesterday she
sounded annoyed that I called. I don’t feel that she’s particularly
interested in me, or even finding whatever zip there was in the
beginning. Push or let her go?

Readier Than She Is

 
Dear Readier than She Is:

I have two very simple rules for people who are looking to date.
Repeat them a few times and see what sounds familiar. First, I only
want to be with someone who wants to be with me. Two, I don’t have
to be with someone just because s/he wants to be with me. Anyone
who passes those two is worth investing some time into, at least to
see if there’s enough mutual interest for things to heat up, not cool
down. Rule three, you get to choose and woo, but remember the other
person has the same options.

 
In this case, I’d send a email that goes roughly as follows. Dear Name:
Are you okay? When we spoke you sounded tired and distracted. If it
was a passing mood, then perhaps I am over-reading. I hope it is
nothing more. But it felt deeper. I do miss more substantive
conversations beyond how&'s work or garden, but we seem to have
drifted into a different, flatter direction. That&'s fine if it&'s conscious,
and I get that your current priorities are work and soil. But it&'s felt
weird not to acknowledge the change. I don&'t have any should in mind,
but there are few enough people I meet that I&'m actually engaged by,
so having things fade to blah seems like a waste. Then see how she
jumps

Dear Jewish Fairy Godmother:

I have been single for five years. I think I’ve worked out most of the
things that went wrong in my marriage and a subsequent long
relationship. Yes I made some of the same mistakes the second time.
But since then I have been in counseling, have shifted some of my
priorities, and have finally decided to start dating. I know there’s
speed dating, internet dating, and personals beyond telling friends
what I am looking for. I actually posted a profile and a picture but the
only people who seem to be approaching me feel far less than what I
am looking for, and I’m not sure I want to reach out to someone I
don’t know. Do you have a strategy that works and is safe?

Finally Lonely

 
Dear Lonely:

Being willing to talk to people you don’t know is a pre-requisite for
dating. It’s always safer and easier to rely on fix-ups from friends, or
meeting people at synagogue, in classes, at volunteer groups, or other
places where you know there’s mutual interests and other folks who
might be able to vouch for them. But times have changed and,
especially in our cocooning culture, many people meet online.

Craft your version of this sample text, or change it completely, and
post it with a decent picture of yourself for three months. I’m new at
internet dating. I’ve been out of relationship long enough to know
what I don’t want to do again, and to be ready to meet another
grown-up aged x-y. I’m interested in meeting people who are a,b,c,
and interested in sharing ideas about d,e,f, and whatever works well
between us. I&'m looking for someone who loves my best qualities and
tolerates my worst ones with patience and humor. I have no agenda
about what or who is a right next, but open to a coffee date to see if
we feel like it’s worth exploring more. If you&'re interested, please send
me an email. Meet only in a public place, preferably with a friend
lurking nearby to make sure things are okay. Write me again if you
have no luck.

Dear Jewish Fairy Godmother:

I am about three months into dating on the internet and
thought I had met someone to date, but to start out as
friends. Read friends = f.r.i.e.n.d.s., not anything more until
I knew if I liked him enough. We emailed a couple times and
then had a phone conversation. In the conversation, after
some niceties and schmoozing, we each communicated our
deal breakers. I was pretty clear and articulate (or so I
thought) that I only wanted to start out slow, and probably
wouldn’t live together with someone until we’d been in
relationship for several years.

In our sharing of relationship history I disclosed that as a
professional I’d made more than both of my ex-husbands,
and among other reasons why the marriages didn’t work
was they each had decided to stop working full-time and the
discrepancy between me earning and them spending eroded
both equality and respect. Now it turns our that Mr. Wants to
Be Next says he lost his whole portfolio in the big bust of 2008
and thinks that if we live together we’ll fall in love. My instinct
is to flee. Am I right?

Gunshy

 
Dear Gunshy:

Yes = Y.E.S!! You are right to want to shut down this prospective
suitor before you get more involved or, at the risk of sounding too
overly cautious, before you reveal too much personal information.
Generally people who are looking for a place to live are also very
charming storytellers. They can spin a hard luck tale into the kind of
sob story you might feel guilty not responding to. That response might
be a small “loan’’ to help him “get back on his feet and get a better
place” or some other sign of a commitment you are under absolutely
no obligation to feel let alone follow through on.

I’d counsel making two lists. These are for you, and you don’t need to
share them with any prospective date before you want to. But they
should be the list of Must Haves and Must Not Have qualities. Repeat
after me as often as you need to: It is okay for me to choose. I do not
have to date someone just because that person expresses interest in
me. If it feels familiar in a way that makes me want to run fast and
far, listen to my instincts. I can do better. It’s all true.

Dear Jewish Fairy Godmother:

I started dating someone a month ago. Or maybe we’re just going to
be friends. Neither of us is in a rush for sexuality, though for different
reasons. I did invite her to a holiday sing-along at one of my friends’
houses. In the inevitable who are you, what do you do, who do you
know conversations, she named a former ex of mine as her neighbor.
This woman and I have a very torrid relationship. Fifty shades of
drama and reconciliation. We parted ways on mutually bad terms and I
haven’t kept track of her. I like the new woman a lot and really want
to be given a fair chance of being a decent partner for her. Do I
confess about the past with her neighbor or let things evolve until it
becomes common knowledge?

Still Blushing

 
Dear Blushing:

At whatever point the neighbor sees you or your new honey mentions
you, she will have to make a choice. You won’t be able to control that,
and if you try and do so you’re more likely to raise enmity and bad
memories. By bringing up the troubled past to the new flame you open
the door to conversations that are ahead of your interpersonal
timeline. I say, ignore the proximity and develop the current
relationship as best you can.

 
When your ex realizes who her neighbor is dating she may try to
defame you in some way. But hopefully by that point you will have
enough good history and positive chits in the relationship that she’ll
have the sense to write off the bad stories as a old chapter in your life
that’s now closed. If not, and she asks you, tell a truth that’s palatable
to you and honest enough to sound credible. Say that it was a storm
und drung relationship and you’re no longer into being or attracting
drama queens. Then hope the new honey believes you. Ultimately she
will have to trust her own perceptions ahead of those of the neighbor.
Or you’ll end up dating in a different part of town.

Dear Jewish Fairy Godmother:

I’ve been single for several years. I’d been in a serious relationship
that fell apart when I realized my partner had been self-medicating a
serious depression for a long time. It’s not that he didn’t talk about his
problems. In fact, that’s mostly what he talked about. But he was
secretly drinking and taking pills at a rate that would have felled a
lesser man. I tried to get him to go into counseling, rehab, or a 12-
step program, all of which he refused. So I ended the relationship.
Now I have started dating someone new and I am seeing symptoms
that scare me, but I cannot tell if I am just suspicious because of my
prior experience. We agreed not to dissect our pasts in the first three
months. Should I say something now, wait, ????

Once Burned…..

 
Dear Burned:

There’s a difference between not talking about ex’s or why previous
relationships fell apart and not talking about something that would be
an immediate deal-killer to how the two of you are relating now. Even
business contracts have cancellation clauses so it’s not like you must
stay in this relationship for the full three months in order to have a
discussion about medical or substance abuse issues. You have a
choice about relating your personal and relationship history with these
topics as part of the discussions, but do not wait to bring up the
subject.

 
I’d start with something like this: I’ve noticed that I respond with
concern, apprehension, and curiosity when I see you do x, y, z.
(Notice so far this is in “I” statements, as most counselors suggest.
Hard to do but often suggested.) Are these things you’re ready to talk
about or am I misreading something? Then see how he responds and
how you respond to how he speaks and acts. The bottom line on the
relationship will always rest on good communications over troublesome
topics, no matter how well you enjoy the good times. No one deserves
to have the shadow of an ex looming over their future happiness. That
means you or him.

Dear Jewish Fairy Godmother:

I met someone I like but I’m not sure how to proceed. We met at a
tenth anniversary party of mutual friends. He’s from the office of the
wife; I know the husband from college (and yes we dated until he met
her, a much better fit). I was seated next to the prospective datee at
the restaurant. Both husband and wife deny it was a fix-up but
honestly it doesn’t matter. He was intelligent, charming, and funny. He
has a job, a home, and a child from a first marriage. So do I. Should I
wait for him to call, suggest we do something together with the kids,
or invite him on an actual date?

Single and Ready

 
Dear Single and Ready:

Congrats on meeting a likely datee. And yes, denial or not, happy
people like having happy coupled friends. So be thankful and also
consider using the connection. Relay to the husband that you liked his
wife’s colleague. Ask if he knows if he is single (a critical piece of info).
That inquiry will get to the wife faster than the speed of light. Then
wait a little while. How long? A few days to a week.

 
If you have heard nothing, ask the husband for the likely’s phone or
email. If he’s in a relationship or otherwise not interested in you, now’s
the time the husband will have to gulp and tell you. But assuming you
don’t get shot down at the starting gate, connect with him via email,
FaceBook, or phone. Note, leaving a message while he’s at work may
feel safer but the child is an unknown variable. I’d suggest emailing an
invite such as this: It was fun talking to you at A and B’s party. If
you’re up for a movie and dinner sometime, let me know. Then go
back to waiting. If he’s interested you should get a response within a
week. Even if it is, My life’s jammed right now but yes I’d like to in the
future, you should not feel like you overextended. Dating is always a
little crazy-making and leads to feeling vulnerable. But he comes with
good references, so give it a shot.