Archive for the ‘Dating’ Category

Sex And OCD

In Dating, Health and Body, Mental Health, Sex on April 20, 2011 at 7:09 pm

Redefining fun, one move at a time.

Hi Yenta,

I have been with my boyfriend for nearly a year now, and it is better than I ever imagined a relationship could be. We live together, we have a cat, and we are both very happy. The problem is this: my OCD makes any type of sex impossible.

We are plenty intimate – we mostly pleasure each other by mutual masturbation – but I can’t even bear to be completely naked with him when we do this for fear of fluids. He is very patient and understanding, but I worry about how long that will last.

He wants to spend the rest of his life with me, but there is a very real possibility that it will be a very long time – if ever – before I am able to have sex, and I am afraid that he will eventually start to resent me for it. Is it possible to have a lasting romantic relationship without sex?

Thanks for your help!

-Keepin’ It Dry

Dear KID,

When you say “my OCD,” it sounds like, “my puppy,” or “ my favorite cat.”  If your OCD is held and coddled, it will snuggle you and remain with you.  I don’t know where you are in your healing process, but I encourage you to challenge your OCD threshold.

That is to say, how far can your disorder go until it runs your life?  Phobias are real, OCD is real, anxiety is real: but human beings have an even realer capacity for healing.  With proper time, care and attention one can reverse, or at least lessen these types of discomforts.

If you have not already tried, perhaps begin first by thinking outside the therapy box, and later, outside the sexual box.   Ie, instead of Psychiatry, dabble in the other healing arts for answers to your questions.  To every thing there is a season, and to every ailment, there is a root. Working with an acupuncturist, a cognitive behavioral therapist, sex therapist, massage therapist,  sexual surrogate, shaman or even a regular psychologist or clinical social worker could begin to address your fears of fluids from a new angle.  Other ideas: doctor-monitored herbal remedies, yoga, meditation, and/or drastic changes in diet.

On the flip side, you could also take another route.  That is the route of acceptance.  This means accepting you will never sleep with your man in the traditionally anticipated way.  You worry about him, and I worry about you.  Are you selling yourself short sexually by so quickly giving your OCD free rein in the bedroom?

If not, maybe this is your threshold.  Maybe this sex, at all, is your triumph in which case I congratulate you.  And the truth is that yes, sexless relationships are possible.  Especially in your case, where you are actually having sex, just not intercourse.  A lifetime commitment to mutual masturbation has happened before and can be a phenomenal way to explore the less-known regions of sexuality and sexual pleasure.

Click here for details on enhancing sex without intercourse.  Everything from new forms of touch and activity, to using other senses and forms, like talking, smelling, etc as means of enhancing your bedroom delights.

Other reads:

Sex Without Intercourse by Gerda Mundinger, a book of anecdotes from real people on how they enjoyed each other without “doing it.”

Let Me Count The Ways: Sex Without Intercourse by Marty Klein, Ph.D. and Riki Robbins, Ph.D.

I am all for you committing to and celebrating a non-intercourse-having existence, as long as that celebration is not a way of quitting and selling yourself and your partner short before reaching towards healing your phobias.  Our bodies are limitless in the knowledge and secrets they hold, you might need to grin and bare it and begin (again) the arduous process of exploring the underside of your OCD.

Merissa Nathan GersonCreate Your Badge

yenta yenta yenta

He Eats Like A Pig

In Dating, Health and Body on April 17, 2011 at 4:32 pm

When you kiss a man, you are eating his breakfast with him. Photo courtesy of Victor Jeffreys II,

Dear Yenta,

I just started dating someone about a month ago.  I really like him, we make a great match in a lot of ways.  But there’s one way in which we really don’t match up: food.  I’m a vegetarian, who loves good healthy food.  Food isn’t just sustenance to me, it’s culture, its experimentation, it’s nurturance.  Michael Pollen’s Omnivore’s Dilemma is one of my favorite books.  There isn’t a vegetable out there that I don’t love.  Cooking is a very important thing to me, and in other relationships it’s been an important part of my connection to the other person.

This guy is exactly the opposite.  Not only does he absolutely hate vegetables, he doesn’t even know how to identify some of the very basic ones.  He’s in his 30’s, but when we go out to dinner, he might as well order off the kids menu– he eats pizza, grilled cheese, hamburgers (no tomato, lettuce, pickles, or onions, of course) and cheese omelettes.  The only color other than white and yellow on his plate is the occasional ketchup to go with his french fries.  Even with beer we don’t match up– I’m always looking for a fun new microbrew or craft beer, and he rarely strays from Miller Light.

I know it sounds like a trivial thing, but this mismatch has actually been pretty challenging for me in our burgeoning relationship.  It’s obviously not just about the food itself, it’s an ideological thing.  Am I overreacting?  Should I try to convince him to start eating like an adult?  Sneak veggies into his food like you do with little kids?  Help, Yenta!


Dear Foodie,

There are a few key points here.  1) You have been dating a month and he already annoys you.  That is not fly.  Month one should be easy and blissful.  2) He eats like a child.  You are what you eat.  There is nothing burgeoning about this relationship.  Get out, and get out now.

I strongly believe that you can decode a great deal about a man based on how he tackles his plate.  Go to a quick-paced eatery and watch one day with a notebook in hand.  Look at how some men gobble, others slice and chew slowly, others eat in small piles or leave flung chunks of food across the plate or the table.  In the way a man approaches what he consumes, you can detect a great deal about his interior choices.

Ie, does he waste food?  Does he care where it comes from?  Is he connected to the world beyond himself, or is food a frenzy, a moment of need rather than a moment of gratitude, consciousness and connection? Also, remember that what we eat affects our temperament.  If he is eating Ramen noodles, his nutrition is low which means his emotional stability is not being fed.  This translates across the board.

This sounds judgemental and absurd, but it is just judgemental.  What are your values?  List them.  Figure out what you need your man to understand, appreciate, be connected to.  He might not have to be a vegetarian to be your lover, but perhaps a conscious eater?  And consciousness can come in a million forms.  This bozo sounds like he is stuck in a fourth grade mentality and it shows in his choice to eat Wonderbread instead of spelt.

I don’t understand why women think it is too much to want someone to be evolved.  That is your god-given right, and really your obligation for the sake of humanity and generations to come.  You must hold high standards and seek a man who has progressed beyond fourth grade because fourth graders cannot rise up and grow to the potential you have inside of you.

Leave him, maybe send him a cookbook, and seek a better man elsewhere.  There may be nothing seriously wrong with this particular guy, but there is plenty wrong with this particular guy when it comes to dating YOU.  You HAVE to be picky because you CAN be picky because you owe it to yourself and to your community to find a man who raises you up, or at the very least, meets you where you are.  Why on earth would you want to spend your good energy educating a child-man on how to eat vegetables when you could be exploring life eye to eye with a man of your caliber, discovering new things and expanding daily.

You didn’t learn to eat well for nothing.  You are an evolved woman.  Onwards and upwards!

Other books to send him off with:

Food Matters: A Guide to Conscious Eating by Mark Bittman

Mindful Eating: A Guide to Rediscovering a Healthy and Joyful Relationship With Food by Jan Chozen Bays

In Defense of Food: An Eater’s Manifesto by Michael Pollan

Fast Food Nation: The Dark Side of the All-American Meal by Eric Schlosser

Ask Yenta!  E-mail a question to merissag[at]gmail[dot]com directly, or using to ask anonymously.

Merissa Nathan Gerson is a fan of
Ask Your Yenta

When Gay Means Guinea Pig

In Dating, Drama, Mental Health on January 7, 2011 at 9:33 am calls Sarah Silverman a "Serious Gay Ally" for boldly declaring she would not marry until "All Americans can legally wed."


When my boyfriend and I first started to date, I heard through the grape vine that there was speculation one of his brothers might be gay. I immediately told the person who told me this to not spread rumors and that it wasn’t true. Please note that I am in no way homophobic! I am extremely liberal and I have walked in numerous gay pride parades in support of loved ones. I want everyone to be happy and I would never judge anyone upon their sexuality.

I met this brother, who is absolutely gorgeous. They have 4 brothers in total. Immediately, we had a lot of respect for each other and spoke to each other with ease. I had asked my boyfriend how on earth could he still be single, and I heard that every girl in their town was trying to hook up with him. It’s his good looks that led everyone to notice when he wasn’t hooking up with the good looking girls who threw themselves at him. Now that he is 24, it does seem a bit odd that he has never dated a girl.

As time went on, I couldn’t help but hear more and more about his sexuality from people from their town.  One night, a friend (even though this was not a FRIENDly move) asked my boyfriend about the sexuality of his brother in front of a group of people. My boyfriend got extremely awkward and didn’t say anything. Since him and I talk about everything under the sun, I thought it was strange he did not bring this up to me afterwards.

Recently, I received a phone call from a friend asking me about the situation. Her sister had told her that her boyfriend (my boyfriend’s brother) had confided in her and told her that the brother wrote them a letter months ago explaining that he was gay, and told them everything.

So at this point, we have been dating for years, and I know the truth. I want to show him that I am here for him no matter what, and I would never judge anyone for their sexuality. I don’t know whether he is embarrassed to tell me, or if he just doesn’t want to admit it to himself just yet. But what I feel most horrible about is that people are talking about it. Should I tell him just how many people have mentioned it to me and claim they know it is true? I have told everyone that has asked me that I have no idea and that it is none of their business to begin with. My boyfriend and I are very serious, and when I think of his family I think of them as my own.

Yours truly,

Trying To Do The Right Thing


The first time I read this and answered this, I thought all along you were talking about the brother, not your boyfriend.  So, disclaimer, the paragraphs that follow this are a sassy response to that assumption.  See end for answer to actual question.

Original still-relevant answer to incorrect reading of question:

A big red flag in life is when someone openly declares “I am not….”  Usually, the need to declare what you aren’t, alludes a bit to what you are.  Ie, if you are so adamantly “liberal” and so die hard “not homophobic” then you would probably not be writing so much to prove it.

It sounds to me like this whole deal with your man’s brother batting for the home team is more about you, than about his homosexuality.  There is no evidence in this story that he is suffering, or that he needs you as an ally.  In fact, there is no imperative for a healthy sexy gay man to come out to the whole wide world.  There is no debutante ball for the homosexual emerging.

It sounds, however, like you really want to host a debutante ball for your boyfriend’s brother’s coming out.  What if he doesn’t want a ball, but wants a small dinner?  Ie, what if this guy is perfectly content being gay, living gay, and not speaking up and out about it?  You sound like you feel a need to communicate your acceptance, desperately.

How to be truly accepting?  Maybe stop heeding the talk and gossip about this guy and his private life.  People talking about him is not his problem, nor should it be yours.  It isn’t as if he killed a bunny, he lives an identity.  That’s it.  People’s fascination or repulsion is generally their own problem.

I would say stay out of it, work on your own relationship to homosexuality, and let this guy live a life in peace.  Be his friend, fine, but not in order to save his homosexual soul.

There are a million ways to exercise this need you have to be an ally to the homosexual community.  Try joining, “Where straight friends stand up for their gay allies,” or join a Facebook group for allies to make your support publicly known.  Posting these groups on your profile is a great way of showing allegiance.  These are ways of also making yourself visible as a safe space should this guy ever decide he needs you.

Below is a list from “The Gay and Lesbian Alliance Against Defamation,” of 10 ways to be a straight ally, without needing, necessarily, to use gay friends as guinea pigs.

10 Ways to Be an Ally & a Friend

1. Be a listener.

2. Be open-minded.

3. Be willing to talk.

4. Be inclusive and invite LGBT friends to hang out with your friends and family.

5. Don’t assume that all your friends and co-workers are straight. Someone close to you could be looking for support in their coming-out process. Not making assumptions will give them the space they need.

6. Homophobic comments and jokes are harmful. Let your friends, family and co-workers know that you find them offensive.

7. Confront your own prejudices and homophobia, even if it is uncomfortable to do so.

8. Defend your LGBT friends against discrimination.

9. Believe that all people, regardless of gender identity and sexual orientation, should be treated with dignity and respect.

10. If you see LGBT people being misrepresented in the media, contact us at

Also check out “What Would A Queer Ally Do,” or “Parents, Families and Friends of Lesbian and Gays, for other resources.

You might, in trying to do “the right thing” be getting too mentally involved.  In lieu of your boyfriend, maybe just ask him about it.  Your fear of the subject isn’t helping.  You don’t need to say, “hey, everyone knows your brother likes men, they are all gossiping!”  Why not just gently mention the truth?  Or, another option…don’t mention it and use the resources I posted to begin to show you are an advocate for the gay community.

Visible advocacy makes it more likely that your boyfriend might come to you.  Either way, be brave, try not to skirt the truth because in cases like this one, it throws everything out of proportion.  Also, try not to presume your boyfriend’s silence is a matter of shame and suffering or that his family needs your help.  This assumption doesn’t bode well for how you view homosexuality.  It is also possible that your boyfriend just doesn’t care if his brother likes girls, boys or smurfs.

Click here to Ask Yenta anything!

Merissa Nathan GersonCreate Your Badge

He Almost Loves Me

In Dating, Drama, Mental Health on November 6, 2010 at 7:27 pm

Three's Company. But two is ideal. (for some...) Whatever floats your boat.

Dear Yenta,

I started seeing a really amazing guy about a month ago. We have a lot in common, to the point where we clicked instantly in almost every way and hung out constantly even before we were dating. Needless to say, I was thrilled to have him. We went together really well, I thought.

The thing is, he broke up with his girlfriend about two months ago, maybe a bit more; not long at all. It was because, for one thing, he found out that she was planning to cheat on him; and for another, they were headed to different colleges in different places in the fall. They’ve remained friends, albeit not talking much, and recently she called him to apologize for planning to cheat on him and to explain herself in some way. This led to him admitting to me that he still had strong feelings for her, that he didn’t think he was ready for a relationship with someone else yet, and that he was sorry for getting into something with me so soon. He really, really likes me, he says, but just…isn’t ready. Okay. I suppose I understand. So we called it off.

However, he and I have remained friends, and there is an extreme undercurrent of…I don’t know how to explain it. It’s more than just sexual tension between us now. More like it seems as though we both wish we were still together.

I understand that he needs space, and I want him to work this out within himself, especially if it means that he and I could maybe have another chance later in the game. But what if it just seems to me like he made a mistake? Is there anything I can do? That was lengthy, I’m sorry. But I’m miserable about this break-up and I guess I don’t know where to turn.


Is He Mine?

Dear IHM,

Thank you for turning to me.

Unless you were totally and completely meant to be, I don’t really understand why you want to give this dude another chance. A) His heart is tangled with someone else. B) With that entanglement, he is dragging you with him through his mud. C) If he enters half-way now, what does that mean about him later, when someone else comes along and he gives you one half and her the other?

A wise woman friend once told me that everything should be judged by the first month of a relationship. She said if it is easy, then it is right, but that it should never start hard. Ie, a relationship that starts hard/complex, ends as such. I will amend her words with a “never say never.” Point? This man might be your future husband, (or your future bad husband), who knows. But it is up to you to set the standard as to whether he is worthy of your heart.

I don’t know very many women who like to be someone else’s emotional leftover. It is not crazy to expect that your significant other puts you first, top of their list, above other loves. In fact, it should be expected that your partner does not tie their heart to another love tree.  You, in a monogamous American construct, are meant to be the one and only. But if you like love triangles, jump!  (Click here for more on safely dating multiple people at once.)

A word on sexual tension: it is common. Yes. It is a common and normal thing to have sexual tension with close male friends, close female friends, close any other type of friends. But what I am weary of in your case is giving that fat nugget of tension too much clout.

It sounds, from all the way here in Jerusalem, like you are being dragged through someone else’s drama as a crutch. Ie. You, the woman who he doesn’t have to invest in nor discard, are there to squeeze his hand when he feels blue. In the meantime, everything you mention is about him, his space, his healing. What about you? Who is loving on you? Are you his healer, his lover, or his girlfriend? Sounds like none of the above.

If he takes the plunge and shows a valiant display of chivalrous affection, if he takes risks, puts one foot in front of the other, gives you solid evidence that you are his queen, not his mistress in the wings, then I would say, go for it. But until then, seek not sexual tension, but sexual gratification elsewhere.

Really want him? Try “Just Friends to Doting Lover: How to Turn That Secret Crush Into a Real Relationship.”

Seriously, though, you deserve so much better. Find yourself a proper prince.

Merissa Nathan Gerson is a fan of
Ask Your Yenta

Going Down With A Dental Dam

In Dating, Health and Body, Sex on October 24, 2010 at 8:15 pm


After a 5-year relationship I recently got back out on the dating market.  I try to be a good lover and as far as I’m concerned that means going down on the women I sleep with. That being said I am concerned about the threat of contracting STD’s this way.  What can I do to protect myself?


Santa Fe, NM

Photo © Betsssssy from

Dear Bryan,

I adore this question.  Why?  Because you are the ideal American lover: you love pleasuring your women and are conscientious about health in the process, a wise New Mexican, indeed.  The bottom line: unprotected oral sex does put you at risk for STD’s and yes, there are ways to protect yourself.

Via oral genital contact you are widely at risk for contracting trichomaniasis, genital warts, gonorrhea (which can cause throat cancer when contracted in the mouth) and a mouthful of other diseases.  HPV and HIV are also both contractable by mouth, and are more so a risk if you or your partner has open wounds or if she is on her period.  Try not to go down on anyone if you have cold sores, bleeding gums, or even if you just brushed your teeth.  These conditions leave your mouth more vulnerable to disease.

What to do to protect, both front and back nether regions?  Use a dental dam.  Originally a square section of latex used as a dental fluid barrier device, the dental dam has evolved as a means of preventing STD’s during oral sex.  Buy at, online or in person at  Toys In Babeland, at local sex shops, the dentist, etc.  If you don’t want to buy one, you can make one with a condom (click here for instructions).  Allergic to latex?  Click here. Also, saran wrap, the NON-MICROWAVABLE kind, is an option.  This, however, unlike the other two latex options, is not a proven defense against HIV.

According to Scarleteen: Sex Ed For the Real World in a post titled “Ode to Saran Wrap:”

Saran wrap is the greatest thing ever. For just $3 one could safely lick 200 square feet of woman (or man or any combination of the two) without worry of bad tastes, pubes, or STDs.

HOWEVER, there are a few things to be mentioned:

1- LUBE, if you do not somehow lube the other side of the saran wrap dental dam it will crumple up into a little ball, but lube tastes bad so don’t get it on the side that you plan to lick. The easiest way to do this is to lube the area to be covered and then put the saran wrap on top of it.

2-SIZE, I have no idea how a condom cut open is supposed to even begin to be big enough to serve as a dental dam. Rip off a HUGE 1.5 to 2-foot section of saran wrap, stick the top of it to their body (lower stomach, lower back, whatever is handy) so that it doesn’t go anywhere (don’t put lube on this part either, otherwise it doesn’t stick)and smooth the rest of it down over their genitals and anus. There should be extra left over, things shift around, you may need it.

3-ADJUST, and readjust. As aforementioned, things shift around, so keep readjusting and holding, if possible, the edges of the saran wrap so that they stay covering that which you do no want in your mouth (get the other person to do this for you if possible, tell them you need to concentrate, and they’re not doing anything with their hands anyway).

Saran Wrap Dental Dam FAQ

Q. Doesn’t a dental dam get in the way?

A. NO. Absolutely not, not even a little, I swear.

Q. Really?

A. Yes, really. If you adequately lube the one side it will slip around and conform to every imaginable shape to fit every crevice you could possibly want to lick

Q. But what if I want to use my hands too and the dental dam really is inhibiting me?

A. Put on a glove, lube it so it doesn’t stick to the saran wrap, and reach under the dental dam.

Also, as gleaned from the advice of a Jerusalem lesbian Tzaddik:

The transition to safe sexual practice can be awkward, it is up to you to make it sexy.  In the process just be careful that a dental dam doesn’t slip.  It is all about the positioning and how you hold it.  Hold it with one hand, spread over the area, and then give the person head.  But I found that if I let go of the dam, I would get really into it and it would slip really easily.”

At that point, just a note, you are exposed to everything you had been protecting against.  It only takes a little contact to put you at risk for a lifetime of disease, so, if you haven’t been tested and aren’t certain of monogamy, practice before you plunge.

A final word on STD testing:

“When it comes to sex that’s the place where people tend to lie the most.  Not maliciously, but so much shame is often involved around sex, it’s often easier to lie about it and not tell the truth.  Even if in a relationship and I totally trust the person, I am going to err on the side of caution.

Even with a trustworthy person, people lie about things.  I am not going to put myself at risk based on the possibility that they may be telling the truth, I am going presume they are lying just to be safe.  Not only that, but sometimes a test is taken too soon, symptoms don’t show, etc.  Even a negative test can later show up positive.”

The moral of the story?  Saran wrap, a dental dam or a carefully crafted condom, some lube, a lover, your mouth, a long night and everyone is safe, happy and satisfied.  And remember, all of the above also applies to rim jobs.  Happy trails.

Ask yenta anything. Click here.

Merissa Nathan GersonCreate Your Badge

Will My Insecurities Drive Him Away?

In Dating, Marriage, Mental Health on September 14, 2010 at 7:24 pm

Hi Yenta,

I am in my early 30s and I have recently begun seeing a really awesome person, and it’s all very unexpected and wonderful. I’m terrified! I’ve never been the marrying type, but I like this person enough that I want them in my life for a while, or however long we’re both happy together — and I know they feel the same about me — but I really don’t want to fuck it up with my insecurity and occasional social awkwardness.

I’ve have two previous serious long-term relationships, and my last one ended about a year and a half ago. I’ve been doing some kind of personal inventory on myself ever since. I dated, I spent a lot of time alone, I cultivated close friends and some new interests, worked at enjoying my job, and generally like myself more these days than I have in a long time and am mostly in a good headspace. I moved to a somewhat remote area recently and in my casing for new and interesting friends somehow managed to cosmically happen upon someone incredible. He makes me laugh, he’s straightforward and communicative, he seems genuine, people who know him really like him, he’s fucking cute and um, etc.

Needless to say, I’m pretty head over heels for him, which is wonderful and totally scary. I have some pretty serious trust issues, and  while I recognise that I will never be perfect (and don’t want to be!) I’m not sure that I can be a good partner, and this makes me reluctant to enter in a new (and likely serious) relationship if I can’t ‘act like an adult’, whatever that means. I’m super nervous when I’m introducing him to people in my life, and I’m afraid to meet his friends and coworkers because I’m worried that I won’t measure up somehow. (His work is more ‘important’ than mine! He makes more money than I do! He certainly doesn’t make me feel this way, but I feel really inadequate next to him sometimes.) It’s not that I still want to play the field — dating and hooking up occasionally was great and all, but my connection with this person is really different — it’s that I don’t know that I’m okay with myself enough to not burden him with my likely eventual nuttiness, and am so over the moon that I feel like a little kid sometimes. But boy, do I want to try. How can I get over this? How can I learn to accept myself enough and not push away someone that is really offering themselves to me in a positive way?

-Crazy Insecure

Out with the old, in with the new YOU! Photo courtesy of Victor Jeffreys II,

Dear CI,

Chances are you are perfectly lovable as you are.  But, just like faith in G-d, we need to cultivate faith in ourselves with steady devotion. This is no easy task. No Ma’am.  This can be a struggle, a fall in the mud and smear your face filthy process.  But every step counts towards immeasurable results.

Lucky for you there are about 72 hours left for inventory before the upcoming year is sealed.  You can hate yourself for not loving yourself, or, within this new relationship you can privately take steps towards self-adoration.  There is a chance that he makes you feel inadequate, and there is the other side of blooming blossoming new love: your inadequacies refuse to hide any longer.

So, use these 72 hours to look at what you fear.  Trust issues, schmust issues.  If he is the one, he is the one. But your work, that inner searching that often comes after a breakup, it also helps to engage such devices during, before, after, and between relationships.  During, however, is clutch.

Maybe you need things to slow down, maybe you need to meet those friends of his at a later date.  Maybe you wish you made more money or that your job were more “important,” whatever that means.  When we fall truly in love we are moving towards a wholer more exquisite version of ourselves.  If you feel inadequate and he isn’t saying you are, then guess who is rapping at your door with Negative Nancy?  You.

There is no shame in therapy for the sake of love.  Maybe you need some extra help reigning in your dark side.  Or, maybe you need to start being your own mirror, somehow curbing the conversations in your head, “I feel inadequate.”  “I shouldn’t feel inadequate.”  “I am inadequate for feeling inadequate.”  And so on.

Love, marriage, trust, commitment:  these things are a choice.  If you choose, then stop indulging the parts of you that are resisting.  Nudge them with love, with gentleness, with friends and with life changes towards the image of the woman you believe deserves this amazing love you are experiencing.  You might be shocked when you realize you are the perfect worthy other half, and this might not happen until you begin to fall as hard in love with yourself as he has.

Want to Ask Yenta too?  Click here.

Merissa Nathan Gerson is a fan of
Ask Your Yenta

Piggyback Dating

In Dating on September 5, 2010 at 1:14 am

Dear Yenta,

Is it okay to date multiple people? I struggle with this question a
lot…Currently, I am dating more than one person and both
relationships are advancing on physical and emotional levels,
although, they are advancing at different rates. At what point do I
have to pick one? I am not stressed out by it, I have room in my life
and head to manage both relationship, but my friends think it is
emotionally immature and greedy… I dont feel unhealthy, and I would
be totally honest if they found out about each other.

Any thoughts?

-Needy and Greedy

Don't pull a Woody.

Dear Needy and Greedy,

The barometer test for situations like these has to do with who ends up getting hurt. If you can honestly say that no one involved will be devastated or destroyed by your dating habits, then what’s the problem? There are plenty of people who believe in open dating policies and succeed in this fashion. They succeed based on honesty, openness, and a clear understanding of what commitment means to them and how to get their own needs met. If you fall under this category of evolved dating, then so be it.

When it comes to love and sex the opinions of others can be poisonous. Every different human has a different set of needs and some are more proactive and more creative about meeting them than others. For all you know these friends judging your behavior are just jealous. Are they getting any? Maybe you getting more than your share is “greedy” in their eyes because somehow they feel you are dipping into their pool of possibilities. Date away, as long as no one gets hurt.

If, however, you secretly want a monogamous relationship and can’t quit all this piggybacking, then that’s a question to sort out within yourself and possibly with a therapist. This same answer applies if your chronic dating is chronic lying and cheating.

For help cultivating multiple healthy relationships at once check out: The Ethical Slut: A Practical Guide to Polyamory, Open Relationships & Other Adventures by Dossie Easton and Janet W. Hardy or Opening Up: A Guide to Creating and Sustaining Open Relationships by Tristan Taormino.

Merissa Nathan Gerson is a fan of
Ask Your Yenta

Long Distance Loving

In Dating on September 4, 2010 at 1:00 am

Keep him close to your heart and the physical distance dissolves. Photo courtesy of Victor Jeffreys II,

Dear Yenta

I started dating my boyfriend in July. Any day now, he’s supposed to
run off to work for a disaster relief agency for 6 to 12 months in
some far-off, war torn, disease-riddled land. While I admire him
greatly for this choice (a choice he had made before we met), it’s
going to wreak havoc on our relationship. It’s been a long time since
I met someone with whom I have so much in common and that I really
enjoy. We are well matched. Although, he is emotionally reserved
in part because he knows he’s leaving. Yenta, is it worth continuing this
relationship or do I cut my losses now?

-Dating a Social Servant

Dear DASS,

If you started dating this man in July, and he knew when he met you that he was leaving, then you need to take a long hard look at yourself. You chose a man who you knew would leave you, and now you are wondering if you should hold on.

If you are as well matched as you say you are, then I am confused by the question. Long distance can be a bitch, but so can losing the most important person in your life. Is he emotionally reserved, or is he not that into you? Or, is he scared to lose you? If you are as well matched as you say you are, then I wouldn’t let this one go just because he is pursuing his far-away dreams.

Have you two talked about what happens next? Where does he stand? And have you had any time apart traveling since you met him? How did that work out? Long-distance relationships really depend on how much the individuals involved are willing to invest, both on their own and as a couple. If you think this do-gooder is someone you should keep around, then I would start fighting now.

And in the meantime, fight with a realistic understanding of what that kind of distance can do to a couple with a wobbly foundation, or how the distance can shrink with skype, effort, a plane ticket and a sincere investment in keeping up with the love. Are you two close enough to cultivate this? If not, and if he is the one, then a year apart on separate paths might just bring you closer when you find each other later and are really meant to be.

Merissa Nathan Gerson is a fan of
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When He Is Too Loud

In Dating on August 12, 2010 at 8:24 pm

You say potato...

Dear Yenta,

I have been dating this guy a few times and he has an obnoxiously loud voice. Every time he speaks when we are at dinner I want to crawl under the table because everybody is staring at him. When is it too soon to tell a guy you have been seeing that he talks too loud?

To make matters worse, when he wants more water he waves his glass and shouts “hello, hello” to the waiter. Last night we went out for sushi and he demanded a spoon and started shoveling the sushi in his mouth. I am totally embarrassed. What do I do?

– Desperately Seeking a Normal Boyfriend in the Big Apple


Well, for this one I summoned the powers of my mother, who said flatly, “Get rid of him.”

My own first question would be to ask why you are dating him, what are his redeeming qualities? Do you like him for him, or are you sitting and enduring these dates simply because he likes you? Is there something fantastic about this rude boy that makes you want to overlook his flaws? Or, are they what take the cake?

My mother says that you can’t tell him what’s wrong with him. She says you need to find another man, or learn to love this one’s weirdness, you can’t change him.

I think it is important to look closely at the ticks that are bothersome about another person. Why does his loudness agitate you? His yelling at the waitress like a slave? Is it something in you, or something in him that needs to be changed? The insensitive details you listed lead me to believe that this man’s flaw is a basic lack of self-awareness and lack of respect for those around him. Why would you want to keep dating someone like that? What does he give you? Also, what kind of bozo eats sushi with a spoon?

There is, though, the possibility that he has something valid wrong with him, in which case choosing patience would be up to you. Again, a decision based on what he does that is positive and enriching in your life.

Only you know what kind of man you are looking for, what kind of things turn you on and off, and only you know if there is more to this story or if the buck stops here, table manners reflective of his general personhood.

Step one in finding New York’s finest dating prospects, in your case, would be drastically raising your standards and believing you deserve the very best in table manners, respect and general enjoyment. Also, knowing what you are looking for in a man makes dating less torturous. This way, if he doesn’t have what it takes you don’t have to agonize over it, you just know. Patience is key when searching for a worthy match. That, and remembering that you should have the very best.

Ask Yenta Anything!

E-mail a question to merissag[at]gmail[dot]com directly, or using to ask anonymously.

Merissa Nathan Gerson is a fan of
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How To Seduce A Bisexual

In Dating, Drama, Mental Health on August 12, 2010 at 8:21 pm

Dear Yenta,

I recently went out with a charming and cute young lady. However, up
until last week, I was pretty sure she was exclusively into other
women (from common acquaintances and context). But we hit it off
really well, and we have great chemistry when we dance. I’m sure she
could be bisexual in this day and age, but I don’t want to offend her
by trying to make out with her if she is really only into girls. I
also have no desire to ask her, “Are you gay?” Any suggestions?

Barking Up the Wrong Tree

Chick chock? No. Slow and steady wins the race.

Dear Barking Up the Wrong Tree,

When you like a straight woman, how do you know she is into you? Would you just walk up to her and start sucking face to express your lust? My guess is, no. Bi and gay women aren’t politically correct specimens, waiting to be offended, they are just women.

List the signs in your mind that indicate a green light with a straight woman and then apply them to your relationship with this new woman. There isn’t a huge difference when a woman is or isn’t into you, if she is also into women. The same rules apply, your mind just gets more wrapped up in the possibility of rejection when all genders are competing.

Give this one time, test the waters, do what you do, gently, nothing too intense, to show her you are looking for more than friendship. Go slow and watch, like you might with any woman who you are truly interested in. If she takes the bait, then keep moving in the romantic direction.

Gay and bi and straight are just labels used for identity markers, politics and convenience. She might be gay, she might be bi, she might be into you, and she might not be. Treat her like a woman who you find appealing, and just see if those feelings are reciprocated. Also, “this day and age” is perpetual, you never know, never knew if a woman you were with initially wanted a woman more than she wanted you. Again, you never know. Just jump.

Ask Yenta Anything!

E-mail a question to merissag[at]gmail[dot]com directly, or using to ask anonymously.

Merissa Nathan Gerson is a fan of
Ask Your Yenta