Archive for the ‘Dating’ Category

Greedy Grubber

In Dating on August 1, 2010 at 8:43 pm

Photo courtesy of Victor Jeffreys II,

Dear Yenta,

I have a friend who comes over for lunch or dinner once or twice a week. He never brings any gifts or offers to help clean up or takes me out to eat or invites me over to return the favor. While I do enjoy being generous and give without the incentive of receiving, I do expect some show of appreciation. Should I say something to my friend?


Dear Annoyed,

In the words of Mother Theresa, “If you can’t feed a hundred people, then just feed one.” In the words of me, tell this guest to get cleaning or get out. I am not completely sure the gentle way around a greedy grubber, but I do know the feeling of giving until you are exhausted of all energy. There is no written law that insists you have to enjoy giving when the receiver begins to leave you drained.

Gentle suggestions, “How about you cook next week?” Or “Would you mind helping me with the dishes?” often suffice. Another option is to reel in the generosity. Sometimes when we think we are being generous we are, in fact, addicted to being needed. Figure out your role in this situation, as much as the free loader’s. Why have you been able to set up this dynamic continually, despite the energy suckage? What are you afraid of in simply asking for reciprocity?

Reciprocity and forced gratitude are very different. “Hey, could you bring lettuce for the salad tomorrow?” is not the same as, “You ungrateful shit, I can’t believe you have never thanked me, or even bothered to lift a finger. I am not your slave wife.” Be good to yourself by learning to ask for help. You might be pleasantly surprised by how willing your guest is to rise to the occasion.

If that doesn’t work, and this person continues to feed off of you, get nasty. You aren’t obliged to be generous unless it makes you feel good, with or without a thank you. Don’t cheapen your gift-giving nature by dishing it out half-heartedly. Create a scene where giving in and of itself makes you feel full.

Your 28-Year-Old Yenta

Merissa Nathan Gerson is a fan of
Ask Your Yenta

She Comes All Day Long

In Dating, Health and Body, Sex on June 27, 2010 at 2:28 pm

What's this crazy pleasure all about!? Photo courtesy of Victor Jeffreys II,

Hey Yenta,

My girlfriend comes so much.  I never know when it is enough.  I am happy she enjoys herself, but it feels like I could make her keep going for days.  How do I know when she is satisfied if she has nearly ten orgasms each time we get it on?

-Gifted in Bed?

Dear GIB,

Ah, yes, the secret age-old dilemma of the multiple-orgasming partner.  Men have, on rare occasion, come to me asking this same question with concern.  Why?  Because we focus so much on the possibility that a woman can’t come, that it seems almost baffling when she comes so hard and so long.

Multiple orgasms aren’t always what they seem.  Often they are a retriggering of a plateau of pleasure in quick succession, so that the orgasm, already brought into being, is retriggered again and again.  For some this is amazing, and for others just one mind-blowing orgasm does the trick.  Whatever floats her boat.

I can actually see how this could be frustrating for a lover, on a number of levels.  With one full-blown amazing orgasm, you know when she is satisfied.  With this many, on and on and on, one wonders what the driving force is, and what an orgasm means at all.  Right?  Because we thought it was meant to be one precious pop.

The limit to this kind of lovemaking does not exist.  It is a good test for you to work on lovemaking being a two-way street.  When her pleasure stops being your pleasure, at the 7th or 8th plateau, you can gently cease and desist.  There is no law that you must keep her pleasure in constant motion.  If the issue is more a wondering about satisfaction, maybe worry about this less and focus more on closely watching and witnessing your partner’s body virtually melt.  This is a gift to bear witness to, so focus less on the goal, and more on the ride.

If, however, you feel she is coming hard and leaving you out, be honest.  Talk about the orgasms, work to better understand her pleasure and voice your own.  At the very least you may gain an understanding of what is happening inside of her.  At most, you increase the connection between the two of you which makes that intense pleasure translate more towards you.

There is always the option of slowing down.  There are millions of ways of inducing orgasms, particularly for a woman like this, so work on that, bringing her to climax with a new rhythm or angle.  Work with her body to see its pleasure lengths and limits.  In the end “satisfaction” is complex.  She is clearly getting off, but to know how it makes her feel, you need to talk.  Communication is the number one ingredient for better and better sex.

For help with your own multiple orgasms, women click hereMen click here.

Also try How to Have An Orgasm….As Often As You Want by Rachel Swift

and Orgasms: How to Have Them, Give Them, and Keep Them Coming by Lou Paget.

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

Cyber-Dating 101

In Dating on June 18, 2010 at 11:23 am

Dear Yenta,

So I recently signed up for an online dating site (JDate).  First day on I see this guy who I’ve met just once in “real” life (though long enough to become Facebook friends w/ him — I asked).  I’d like to be better friends with him either way, but first have to bridge the awkward divide…

Ideas to write to him? A friend suggested, now that we’re Facebook friends maybe we can be JDate friends. Groan. Any better ideas Yenta?


Start small. Photo courtesy of Victor Jeffreys II,

Dear J-Lo,

There are a few laws involved in maintaining self-respect and limits when it comes to online dating.  I have a full handful of close friends who have discovered the loves of their lives online, so here are a few words to the wise.

1)  Be honest.  Be real.

2)  Not too honest.  Not too real.

Basically, you want to be giving a safe version of “you” out to the world.  One that if they take it, awesome, and if they leave it, no skin off your back.  If your stakes are high in an e-mail, he will either buy it and marry you, or be full on freaked by your desperation.

Some people can go full throttle with the online dating scene, partly because they don’t fear rejection. It is really a matter of how sensitive you are, in general.  Cultivate that fearless attitude, and you are golden.  It is done by simultaneously opening yourself and protecting yourself.  Giving just a little, watching, and continuing.  Like advancing towards a pirate ship.  Only in this case, you want to join the band of pirates.

With this guy I say just be straight up and say what you want.  “Hey!  Funny finding you here.   How are you?”  See how he takes it.  Go gentle so he can breathe.  With an “I want you, I always have wanted you, now we are e-friends in more ways than one,” he might suffocate.  Or, why not wait for him to come to you?  Not so unheard of.

Also, be wary of seeking your affirmation of self from e-dating.  If every conversation makes or breaks your self-esteem, you are in for a beating.  It is like weeding a garden until left with exactly what you hope to grow.  It takes time, differentiating the vegetables (lovers), the wild from the sustainable.  Capiche?  Love comes from you, from your family and from your friends.  Dating is just a fun social perk until, possibly, it turns into love.

In the end though, it is dating, i.e., a way of packaging and showing a sliver of yourself in hopes that someone else’s sliver of self likes you, at which point the sliver turns into a full on self-exposure/love affair.  Trust yourself and go easy on the gas.

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

Rectal Surprise

In Dating, Mental Health, Sex on June 14, 2010 at 9:06 pm

This intense pleasure zone ironically threatens the perceived manhood of some of the manliest of men. Photo courtesy of Victor Jeffreys II,

Dear Yenta,

My boyfriend likes surprises. I bought him a t-shirt that he had commented about for his birthday, and after he opened it and told me how much he loved it, he made a comment about his lack of surprise at the gift. Since there were no more holidays coming up, I decided to surprise him in the bedroom, hoping to satisfy his need for that wow feeling.

I lotion-ed him up, lathered him down, and then shoved a small vibrator in his ass, to his surprise. Needless to say, he did not like my surprise. It has been three weeks since my attempt at surprise and even though I have apologized several hundred times, he won’t strip down below shorts. I have a non-existent sex life now, and even worse, every time I start to get a little frisky in the bedroom, he turns bright red and tells me that he isn’t in the mood. How do I get my lover back?


Dear A-Hole,

I started by asking two men what they think.

They answered:

“Why needless to say he wouldn’t like it?  Some men really like surprises, anal surprises and toy surprises to be specific.”

“Stick a vibrator in your own ass, you’ll get your lover right back.”

“Needless to say, the vibrator is for you, not him.  Lather up, lotion down and stick it in your own ass.”

Sticking something in a man’s ass without warning may very well provoke a retreat into his shell.  There are all kinds of men.  There are men who like being penetrated, men who were raised to be the penetrator and ride a bull.  There are men who like things in the rear, and men who fear the pleasure they find in that area.

Without talking to him, you never know the cause of his repulsion.  Chances are, though, that he might not even be able to talk about it.  My guess is that there is complex shame around what occurred between you, so tread lightly.

Apologies will do nothing.  You need to show your understanding through action, make him feel safe, let him take the reigns.  Give your boyfriend back a sense of power.  Let him make some decisions.  Show him, through your behavior, that you will not push his limits unless asked.  This is partially about a loss of trust.

He may have liked it and have a fear that enjoying pleasure in the ass (which makes sense because there are some amazing nerve endings in there for men) implies he is somehow gay.  This is common male homophobic confusion.

Or, your boyfriend may have a history of sexual abuse and you may have just triggered memories of his body being violated and/or penetrated.  We think male rape victims don’t exist, but they do, they abound, and we women, so often used to being on that side of the fence, need to be sensitive to that possibility in our lovers.  For information on myths and facts of male rape, click here or visit  Also, try reading this City Paper article.

Whether a survivor of abuse or not, to treat him like one might help win his trust back.  Try reading these tips, “Recovering From Rape: Healing Your Sexuality” as barebone guidelines for rebuilding intimacy after trauma.

He could have power issues, gender role issues, abuse issues, butt issues, trust issues, an allergy to plastic.  Whatever it is, if you like him, you need to earn his trust back.  If you are gung-ho on the anal, he may need some proof that this sexual practice isn’t so crazy.  Some men grew up in the sexual boondocks.  Try helping him, if that feels right.  Click here for assistance.

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

Lesbianism Ain’t Always Easy

In Breakups/Divorce, Dating, Drama, Mental Health on May 27, 2010 at 3:29 pm

It wasn't easy for Callie Torres to embrace this moment on Grey's.

Dear Yenta,

I’ve been in a relationship with someone who has been reckless with my heart.  I am in my first lesbian relationship. We began dating shortly after she was broken up with by her ex-gf.

After a few weeks of dating me, she dumped me for her ex then a week later asked me to be her gf again. I was really hurt but still had strong feelings and we got back together.  Should I stick it out knowing that she could possibly get back with the ex again?


Woman Burn

Dear WB,

What I read when you say someone has been reckless with your heart, is that you opened your heart to the reckless.  I spent many a year as a Women’s Studies major, and then many years to follow attempting to ditch the victim/oppressor mentality.  We choose our lives, and shape them accordingly.  This woman is abusing you because she can, because you said she could.

In this case, there are a number of things you can learn from this new relationship so as to guard your heart from suffering in the future.  For one, be aware of your emerging self.  If you are newly out, or newly consummating your gayness, this might leave you vulnerable to wicked edges.  If the women you are dating in this first phase aren’t solid, caring and together, you might be more susceptible to recklessness.

It is not easy, those first weeks, months or years of an emerging identity in a society that still debates the legitimacy of lesbianism to begin with.  There are a long list of issues that come to the surface ranging from homophobia to questions of scripts and behavioral norms.  Do you have a community supporting you?  Are you using this woman as your support network?  That could be disastrous, and also explain why you would put up with this type of cruel flip-flopping behavior.

One book that comes highly recommended is How To Be A Happy Lesbian: A Coming Out Guide by Tracey Stevens and  Katherine Wunder.  Look for GLBT events in your community, or find out if there are peer groups, support groups, or basic fun events where your community can expand beyond this mean woman.  Also, try calling the GLBT National Support Hotline at  1-888-843-4564 instead of funneling yourself into this woman and her split heart.  They also offer Online Peer-Support Chat.

Another thing to beware of with both women, men and in-between, is that anyone who is freshly out of another relationship may not be totally present for you.  No matter how much this woman may like you, and no matter how much you feel for her, her heart is still tied up with the past.  This means she can’t be the girlfriend you deserve because she is still busy being a girlfriend, or navigating the oddities of being an ex-girlfriend to her ex.

It’s as if this woman gave you an awesome new toy(her), and then realized suddenly that she wanted it back.  When we receive people into our hearts and bodies we want to be sure that they are as present, as unattached and as loving as we are.  This recklessness that you refer to is her problem, but more so, it is your problem that you engaged in a relationship with the reckless.

Thus, YOU have been reckless with your heart.  Be gentle and patient in seeking women to love.  The beginning of a lesbian dating life is not always easy, but the signs of a maladjusted lover run clear across the board.  Steer clear of women in love with other women.  You will find another person to love, one that is as loving as you are.  In the meantime, look for some solid queer friends to support you in your identity and weave your way out of this destructive relationship.  You deserve a love all your own.

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

Pursued by a Cheater

In Dating, Drama, Mental Health on May 25, 2010 at 1:25 pm

Dear Yenta,

I am a college student living in the dorms. Last week, I met one of my friend’s roommates at a campus celebration. A bunch of us were hanging out and this guy (I’ll call him B.) was talking to me a bit, etc. After the party, he added me on Facebook and started talking to me on Facebook chat right away, commenting on what I had been wearing and asking me a bunch of questions. (This guy, by the way, is SUPER attractive.)

Over the past week, we have talked a lot online and hung out once in person (but we were with his roommates as well), but he always tells me that I should come visit and is pretty blatant about hitting on me. Last night I was hanging out with some of his roommates and someone spilled that B. is moving out of their apartment and in with his girlfriend. (Apparently they had broken up and recently got back together.) WHOA–SHOCK.

He has never mentioned having a girlfriend to me. By chance, right after I found out, he messaged me on Facebook chat, and when he found out that I had been with his roommates, he asked why I didn’t come say hi. He doesn’t know that I know about his girlfriend and his move-out plans, so I carried on a short, polite, relatively banal conversation, even though I wanted to ask him point-blank about the girlfriend and us. Nothing has happened between us (thank goodness) except some flirting, because I wanted to take it slowly (I am a little bit weary of pretty boys), but I developed a pretty bad crush and the messages he was sending me made it seem like he was interested too. I don’t know if I should ask him about the girlfriend or let our little flirting game go on or cut him out of my life completely. I’m sure I can get over him quickly because I haven’t known him for that long, but I feel really hurt and betrayed and don’t know what to do. Please help!


-Crush Has a Girlfriend

Bacon, Egg and Cheese = Un-Kosher. Seek love elsewhere. Photo courtesy of Victor Jeffreys II,

Dear CHAG,

There is nothing worse than feeling amorous towards a seductive man and then suddenly learning he is taken.  This sucks on so many levels, but the worst level is that you liked him, he jump-started your heart, and then it turns out his integrity is down the tubes.  That is a sad dating moment.

According to Esquire’s article, “Why Men Cheat: One man’s unfiltered, unadulterated explanation. Well, maybe a little adulterated,” by Anonymous, “If you cheat, you must believe this much: that fated love is a lie, and monogamous love a deception. If you cheat, these two sentiments are your guiding light.”

A really intuitive woman knows that a man who cheats is hurting.  There is something achey on his part, involved in hurting those he loves.  A lottta women love pained men, because they get to potentially swoop in and save them. Or, get cheated on or cheated with.

So there are like six hurts here, your hurt at losing out on a crush, your hurt in learning your crush was a douche, your hurt that is really his hurt passed through action, your own hurt that would lead you to a man like this, and so on and so forth.  Even monsters garner our love when they suffer.

Blah.  With all that hurt maybe spend a day at Spa World and stop Facebook chatting with the mofo.  He can hit you up all he wants, but you really need to guard your own and not worry about him.  Maybe he would one day be a friend, but I doubt it.  Cultivating a community of friends is a deliberate and important act, not one built on a foundation of deception, lies, and manipulative behavior.

This guy sounds like the dumps.  The sooner you cut him loose, the sooner you have space in your heart to welcome new, pretty, kind AND truthful suitors into your court.

According to How to Spot a Cheater Within 15 Minutes of Meeting by Paul Dobransky, you fell into the following traps.  Please avoid them in the future.

1) “They are VERY controlling, or VERY easily “controllable” (overagreeable)”

When a man spittles up compliments like a baby and his breast milk, you know you are barking up the wrong tree.  Love matures with time, not incrementally based on your hot outfits.

2) “They use the word “SHOULD” a great deal as in “You should sit down over here,” “You should get a different haircut,” or “You should treat me like a king/queen.” This person is likely to CHEAT.”

Yes, your little friend pulled this one on you repeatedly.

3) “They are “oversensitive.” Try a little sarcasm and see what they do.”

4) “Neediness. (Whether an attention hound, or a passive, shy type) Alongside “oversensitive” is any other similar word: “high maintenance,” “prima donna,””entitled,” or otherwise one with low self esteem, they are more likely to cheat. You will have an intuition about this, a feeling like they are pulling on you too much, leaning in on you. Scan your emotions for this, and also notice whether their body language actually physically is too close to you, leaning toward you all the time, or too much attention placed on you. This person is likely to CHEAT.”

5) “Trouble with the word NO. They either can’t say NO to you or others, or can’t HEAR NO gracefully from you and still be interested in continuing conversation.”

Ah yes, you say bubbye, he says hello.  Ugly.

And the clincher:

6) “Outright abuse or lying.”

Homeslice lied in his pursuit of you.  Period.

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 To Say “I Love You”

In Dating, Drama on May 17, 2010 at 8:36 pm

Dear Yenta,

When is too soon to say “I Love You?”


Mr. Lover Man

Love is about nudity. Make sure they can handle seeing you bare your naked heart. Photo courtesy of Victor Jeffreys II,

Dear Mr. L,

First, a disclaimer.  Only you know yourself and your lover.  No Yenta can tell you what’s best.  But here are some ways to derive a system of gauging love and its profession.

As one woman once said, recoiling at the words “I Love You,” “That’s the nicest thing you can say to anyone, isn’t it?  Thank you.”  This coupled with a severe look in the eyes and rigid body language is the reaction, I am guessing, you are seeking to avoid.  The question is less about when, and moreso, about how, to whom, where, etc.

Say it too soon, some people run.  Why?  For a number of reasons.  Here are some rational explanations as to why those three words can be terrifying, followed by a list of ways to safely profess your undying love to anyone, anywhere, anyhow.

1)  Commitment Phobia

Early declaration forces decision into the relationship.  Ie, commitment.  It is an ultimatum in some ways, like saying, “this is where I am, up here on the love platform, and if you can’t join me here yet then we are through.”

2) Self-Hatred

Saying “I Love You” is also a big witnessing of another.  To be seen in our entirety and then loved, as sweet as it sounds, is hard.  We are programmed to doubt ourselves, so when someone says, “I don’t doubt you, I adore you,” our fears come shooting out.  Ie, “Am I worthy?”  “Will you still like me in a week?”  “You don’t know that I killed my cat when I was five, when that comes out you will regret those three words.”  Things like that.

3) Falsity

The Sakyong , Jamgon Mipham Rinpoche once spoke of how the act of declaring your love is a moment once-removed.  “I Love You” is really a redundant expression.  When love is real and alive and vibrant it lives between two people in their eyes, their touch and in their actions.  To then state it is an afterthought to the reality of the love that was already alive between you to begin with.

One way to cope with the fear that it is too soon, is to express your love rather than declare it.  A declaration without the backup actions will scare anyone away.  That, and the human heart and mind can only handle so much adoration in one dose.

4) Vulnerability

Saying “I Love You” is making yourself extremely vulnerable, exposing all of yourself.  We build trust and intimacy so it is strong enough to hold the intensity of really loving and seeing each other.  If the web isn’t strong enough, we lose that foundation and find a closed-door in our face.

I once fell in love and professed my feelings so emphatically and intensely that the boy ran away for weeks before secretly admitting his mutual adoration.  It was too much, like love vomited all over him, like a basket overflowing and his arms couldn’t hold it.  Give the person you love enough love that they can hold it, see it, feel it, touch it and know it.  If love is somehow palpable, held, breathing and doled out in digestible doses then your loved one will better be able to meet you.

Ways to Gauge the Moment and Properly Profess

1)  Evaluate Intention

The questions you want to ask yourself before surrendering your heart in the name of a four letter word include: What do you lose if you say I love you?  Would it compromise anything, the sex, the honesty?  Do I love this person, or lust and hunger for them?  Am I professing to pin them down, or lift them up?  Can your relationship stomach this admission, even if it is true? Make sure this is love, not just hunger for sex and security, etc.

2) Actions Speak Louder Than Words

So say I love you when you feel like it, but be sure your actions back up your words, and that your words aren’t some way of cornering someone into commitment.  That isn’t love, that is ownership.  Because you want it to be true, that simple truth needs to resonate with your behavior.  If you give your partner a cold shoulder most of the time and suddenly spout loving words, they might coil in fear.  Don’t just say it, do it.  Saying I love you without action, is a lie.

For help, click here for 60 ways to say I love you.

3)  Time Will Tell

When in doubt, wait.  Generally if it is torture to hold it in, you need to start expressing yourself, stat.  But it is a hard and thin line between doubt and fear.  Doubt can be guided by intelligence and intuition, whereas fear is laced with cowardice.

According to some secret sources, before the two month mark is too soon, at the four-month mark is perfect.  According to a sage, wise at the art of love and poker, “It’s never too soon to say I love you, Merissa.  I’m not one for rules and regulations when it comes to these things.”  Advance day by day, step by step, with your own heart thumping loudly and leading the way.

Click here for a list of 100 languages in which to say “I Love You.”

Click here for a CNN article on why women should wait to say it.

Click here for an article on The Different Ways Men Say “I Love You.”

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

Grabs Her Boobs In Public

In Dating, Drama, Sex on May 15, 2010 at 6:49 am

Keep those filthy paws off her silky drawers. Photo courtesy of Victor Jeffreys II,

Dear Yenta,

When I am with my girlfriend at parties, I like to sometimes grab her breasts in public and she seems to like it too.  Some woman came up to me tonight and told me this was wrong.  What?  Who is she to tell me what to do with my girlfriend?  Is it wrong, really?


Copping a Feel and Liking it


Well, I guess there are different standards for each woman.  Some women don’t mind if you grab them in public, and others do.  Some men don’t mind having people witness their sexual affection for their woman’s parts, and others do.  It comes down to a matter of personal preference.

Is it “wrong” to grab her boobs in public?  That is really for her to determine.  My only caution is this: some women have a hard time saying no, even when it feels wrong.  Some women like pleasing men and will let go of their own dignity to do so.  Some women don’t know that they can expect a man not to grab her breasts in public.

And then, some women get off on it.  I personally abhor witnessing people grope on each other in ways that provoke the imaginings of what happens behind closed doors, but that is just me.  I prefer a PG display of PDA, and am generally irritated when I see things, like, for example, tonight when I watched a woman loop her hand tightly in the inner part of her man’s groin, rubbing one hand brusquely across his penis.  No.  When I reached for another potato chip on the BBQ buffet, I didn’t expect to see that.

But my discomfort is my problem.  Grope away if you really think your woman friend feels respected, despite you being inside of her shirt in front of strangers.  The only way, though, to really know if she is down for some staged feeling up is to ask her when you aren’t already mid-act.  Talk about this in private, perhaps sober and in daylight, to be sure you aren’t accidentally pushing your lover into a space of shame and discomfort.

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

Is It A Date?

In Career, Dating, Drama on May 12, 2010 at 2:08 pm

Dear Yenta,

How can I tell if my next meeting is a date?  We got drinks to talk business and then we got dinner again to talk business.  And then, we got dinner again to talk business and I paid.  Then in an e-mail we talked a little business, she said, “Going out of town, when I get back, let’s hang out.”  Which is different from business, but our business is kindof a business of hanging out. Is it, or is it not, a date?


Whatever you do, try not to be creepy/skeazy or sleazy. Photo courtesy of Victor Jeffreys II,

Dear Confused Cornelius,

A few things…

1) It is not a formal date. A date is obvious, and not veiled in business.  A better question, Is it romantic?  This only you and this woman know, and to test these waters all you need to do is dip a toe in and check the temperature.  If it is freezing, retreat and continue business chatter, if it is warm, proceed.  You know this.

2) When you paid for a meal you tilted the power dynamic which is often, oddly, a tilt towards romance.  Whenever it is not split evenly, you are making a statement about something, somehow.

3) Don’t mix business with pleasure.  This is simple and sane wisdom of the sages and is a good rule of thumb to follow…depending on the type of business.  If advancing sexually towards this person could potentially complicate your job and threaten your professional relationship, then heel, boy, heel.  If your business is one that can handle a bending of boundaries, OR, if you really think this is for real, then proceed.

The semantics of dating are irrelevant.  All that matters is whether you really want this person, and if so, then fearlessly pursue them and deal with the consequences, for good or for evil.

Or, when it doubt, said a rogue therapist of mine, do without.

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

Advice From Your Moms

In Dating, Marriage, Sex on May 9, 2010 at 7:08 pm

We love our mothers because, among other things, they made us cool. Photo courtesy of Victor Jeffreys II,

In honor of Mother’s Day I anonymously interviewed a handful of America’s finest matriarchs. Before we begin, a humble shout out to the mothers we have lost whose advice on these topics would have no doubt assisted women everywhere in living on their wilder side, including but not limited to the fabulous Kathy Blane, Sherry Millard, and the many others who shaped the better of our generation. You are missed. 

Without further ado, The Wisdom of Your Moms

Advice to a virgin: 

It might not be great the first time. 

Lubricate yourself. 

Go for it! 

Hold on to it, it’s not going anywhere. 

Get birth control – you never know when children will happen. 

Advice to a woman who can’t come: 

This is if there isn’t some medical or other serious reason she can’t: 


Have a drink.

Get a sex toy online so you don’t have to deal with any hassle. And then just teach yourself how to do it. 

Bedroom advice for men: 

Slow down, take your time, listen.  

This is not a race to the finish. 

Secret sexual knowledge: 

Be sexy. 

Be open to try new things. 

Know what your guy wants. 

How do you know what he wants? 

Men don’t verbalize normally, but they do try to lead the way and you just have to trust and go for it. 

How do you know if there is more to him as a lover than what he says he wants? 

Show him.  

Push his limits. 

Be totally open. 

Follow the moment. 

Advice to a woman with many lovers: 


Get rid of most of them. Pare it down and simplify your life. 

Advice to a woman with a cheating partner: 

Get rid of him – unless you have a child. And even then, I don’t think I could deal with it, but some people can. 

Advice for finding a husband: 

Don’t try to find it – they will come to you.I was asked by four men for their hand in marriage but it wasn’t something that I wanted to do. The fifth was the man I married. Sometimes women scare men away because they so need to get married. 

There’s a difference between declarative intention, ie, I will find a good man, and needy desperation to transform a lover into a husband. 

Guys take their own time. The more you push, the more they move away from you. 

Demand to be treated with respect. 

No man is going to want you if you don’t have self-respect. If you expect respect, you will get respect. 

Don’t give it away for free. 

Pursue your interests and have a good time. 

Advice to a newlywed: 

You have to stop thinking about yourself. Even in this age of equality, it’s compromise. You have to go 60/40 in a marriage to make it work. 

The real thing is, you have to compromise, but you also have to be yourself. Deal with who you are and the other things will fall into place. 

Be sure that before you get married, you know who you are marrying. People don’t change. A lot of women expect that marriage will transform their husband into a new and better person. What you got dating him, you will get after the wedding. After marriage he will still be him, so be sure you like that person. 

The party is over. The work is here. 

There is always a downside after the performance of a wedding, relax, you will get through it. 

Sometimes women are so focused on the wedding that they forget there is a marriage that happens after it. Marriage does happen. 

Talk to your spouse.Enjoy it now, it’s never going to be as simple as it is at that moment. It will get better, richer and more complex, but never as simple and wonderful as those first few months. 

Advice on good living: 

Just be happy.  

Don’t have crazy expectations and don’t push people. 

Don’t wear yourself out.   

Shore some of the responsibility, let others be there for you. 

Don’t try to do everything. 

Do everything. 

And finally, to my own mom, the invincible: I love you. 

Happy Mother’s Day from Your 28-Year-Old Yenta!!! 

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

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