Cherry Jubilee

Dear Bartender: I am 24 years old and still somehow have not managed to lose my virginity. Heaven only knows why, as I am considered a quite attractive young lady. It just didn’t happen. I don’t just wanna go and bang some guy because of all the psychological effects the notorious first time is supposed to have on a girl. On the other hand, I’m pretty sick of missing out on all the hot, hot casual sexin’ going on all around me.

Now there’s this one guy who really means a lot to me. He’s made it perfectly clear that he is not interested in pursuing a relationship, which is fine ’cause things like that just can’t be forced.

Nevertheless, do you think I could ask him to be my first?

–Slightly Desperate

Dear Slightly: These things can’t be forced indeed. And I hope you’re not expecting too much of your first time, cuz the notorious effects aren’t just psychological. Good sex takes practice. Practice, practice, practice!

Which is why you wanna start practicing. I get it. Speaking of practice, briefly allow me a pause to accept that there doesn’t seem to be any question out there that I haven’t answered already.

Sure, go ahead. He’s not your brother, is he?

Blitzkrieg

Dear Bartender: As far as I can see, I am the first German on your page, so “Guten Tag” and “Wie geht’s” to you!

I am very interested in a band member of an American band that will be touring in Germany soon. We have written e-mails almost daily for the last year and a half after I saw him at a gig and fell in love with his shy smile. Our communication ranges from tame to outright flirty.

Yet despite the flirting, he seems strangely evasive. In London, where we first met “properly,” he suggested a steamy night together – then immediately excused himself and said that he was being “too cheeky.” After he had returned to the States and we continued writing e-mails, he mentioned that it was very responsible of us not to have fooled around. I’m not a supermodel but I certainly have charisma and curves in all the right places and – thanks to many years in the service industry – an open and friendly approach to people, although I can be very outspoken at times. My best friend (who is a man) claimed that I probably intimidated the guy. Apparently, I seem to do this to people.

He keeps referring to himself as “weak” and claims that he would get on my nerves after three days. He plays in Germany at the end of the month it’s also his birthday and I would like to give him a nice birthday kiss. A nice DEEP birthday kiss. How do I get past his shyness and his evasiveness and do you think he likes me at all?

–Flustered Waitress

Dear Waitress: Three days? He’s being too kind. He got on my nerves after three paragraphs.

His use of “cheeky” notwithstanding, he’s clearly an American. Americans can be direct in many ways – but sex ain’t one of them.

Tell him you’d love to get to know him better, but you don’t get the whole cat-and-mouse thing. Tell him it’s not the way people do things in your country. Ask him to explain how people do this kind of thing in America. Act interested in his answer – then, halfway through it, plant your birthday kiss.

Note to readers: You may have noticed that I haven’t blogged much lately. Congratulations on being observant.

Dads I’d Like to Do Once

Dear Bartender: My young daughter’s best friend’s dad is single, retired, seemingly rather well off, and taking a bartending class for fun. I’m single, poor and love to drink. I’m thinking of broaching the subject of him using me as a guinea pig for his bartending skills as a segue into checking out whether we might hit it off. It might be awkward but that’s really never stopped me from sticking my neck out before.

My question is, what drink or drinks should I ask him to make me that will be sending the message that I’m available? And don’t say a Harvey Wallbanger.

–MILF

Dear  MILF: Since from your tone I’m guessing you’re also going to rule out a Sloe Comfortable Screw Against The Wall (or even better: a Sloe Comfortable Screw Against The Wall With Satin Pillows The Hard Way), I’m not sure what’s left. How about you just do the old fashioned thing and get him drunk? Short of hitting him on the head with a club, it’s about the easiest way for a woman to see if she and some guy she wants to fuck can manage to “hit it off.”

Don’t let your left hand know…

Dear Bartender: I got married fifteen months ago. On my honeymoon, I was surprised to hear my husband tell me that I was no longer allowed to masturbate. I’ll admit that I agreed to this at the time — but mostly because we were then regularly having sex.

Since then, sex has become infrequent. Am I obliged to abide by his rules?

Sincerely,

Jennifer

Dear Jennifer: Masturbation is not to be confused with infidelity. While there may be circumstances under which a spouse may legitimately request limits on his partner’s masturbation (I’m thinking of a non-cheating spouse who masturbates but denies her husband sex), to masturbate is not to cheat. It doesn’t matter whom you think about when you masturbate; it’s not the same as cheating.

My opinion is this: If masturbation doesn’t get in the way of a healthy sex life with your husband, he has no business telling you not to do it.

Blame Canada

Dear Bartender: Please help me. I need to “break up” with my ex-husband.

We divorced two years ago but he still seems to think we are married. There are no kids involved, and we dissolved all joint property last year (thank god!). Nevertheless, he calls me every day and thinks that just because we occasionally have sex once or twice a month that we are still “a couple.”

This is seriously getting in the way of me keeping a boyfriend. My last potential b.f. surprised me one morning showing up with a picnic basket and a whole day of sex planned. My ex-husband had just spent the night and subsequently was hiding in my hall closet! I admit it turned me on knowing he could see us through the door but I was terrified that he would get hurt if my b.f. found out. I don’t wish this man any ill, I just wish he’d go away.

Please don’t tell me to stop having sex with him. Tho the marriage wasn’t great, there was nothing wrong with the sex. (Is there anything, ever, wrong with sex?)

Just need some advice.

Sincerely,

TMJ

Dear Sex Addict: I would never steer you away from great sex. Christ, from the sound of your letter I could hardly peel you from it with a hot spatula.

Yet you’re clearly stuck. It’s not your husband who can’t let go — it’s you. I’m gonna go out on a limb and suggest that you actually don’t have a problem, that you’re pretty happy with the way things are. You only need to set one or two boundaries. My suggestion: handcuff him to the bedroom radiator and make him watch as you fuck whatever crosses your threshold. You will drive him crazy — and toying with his emotions is clearly what gets you off.

To have and not to hold

Dear Bartender: My wife and I no longer have sex, and I’m sorry to say that this situation is apparently non-negotiable. I have proposed having an affair with a woman who lives in a nearby town. She and I have already had sex. I do not want to divorce my wife, but I still want to have sex. My wife says I can’t have an affair. I say, no marital sex, no business calling the shots.

Bartender, what do you think?

— Frustrated in the MIdwest

Dear Midwest: The affair is yours to have. Your wife may end up divorcing you, but she’s wrong to think that celibacy and monogamy are the same thing.

I’m eager to hear if my readers have more to add to this topic.

Papa Was A Rollin’ Stone

Dear Bartender: My 50s style boyfriend and I are trying to make the transition to just being friends, but we’re having trouble, erm, “unlearning” some habits of the physical nature. He’s just too handsome, with his hair all slicked upward, his two-tone shoes and his key lime pie 59 Chevy. But he wants to run off ~ solo ~ to LA to be an actor, and I’d like to start a family. It’s a hopeless affair, especially as I turned 39 today and my eggs are running amok. How do we stop this madness and get on with our lives? Garlic? Fisticuffs? Ill-fitting jeans?

~Yolked up

Dear Yolked: Great sex is great sex. Just because he wants to bolt doesn’t mean you have to give up the blue parts if you’re still having fun. Just memorize everything he’s doing and start thinking of ways to to teach it to the next potential Baby Daddy.

If great sex were food, it would be a soufflé — either dessert or the whole dinner.

Hello, I Love You

Dear Bartender: How does one know if he/she is good looking? Is there a checklist or something you can run through to get the answer?

–Unsure

Dear Unsure: Start believing it the 10th time you hear it. Ten times from ten strangers is great, but that’s not to negate the value of hearing it 10 times from your spouse.

A Man Needs A Maid

Dear Bartender: I am a straight white male into playing Maid. Doing it for money TOTALLY turns me off, so please don’t suggest I go professional. I simply want to clean women’s houses, either naked or in a uniform, while Madam either supervises or goes about her business. (She can be clothed or unclothed, as she wishes.) If she wants to tell me I’m doing a bad job and tell me how I can do it better, that’s great too. Sometimes I’ll have to trade parts of my uniform for another chance at proving myself. All good.

My question has to do with a woman whose husband came home “unexpectedly” after I’d completely gone stark naked in my effort to clean this woman’s book shelf to her satisfaction. This man not only got naked himself, but he took a totally authoritarian tone with me and ordered me to clean the kitchen on my hands and knees. I didn’t like taking orders from a mere man, and to make things worse I’d already cleaned the kitchen! The woman seemed to be having the same amount of fun with or without the husband, so I don’t see what he really added to anyone’s experience. Needless to say I did a half-assed job “re-cleaning” this man’s kitchen but I’m not sure he even noticed.

My question: at what point could I have said no? And if the lady calls me back, should I go?

If it makes any difference the husband is just as overweight as I am.

–ManMaid

Dear MaidMan: You rolled over far too quickly, Lassie. Madam would have loved nothing more than a good dogfight. When you go back, you’d better wear something extra special you can trade for that second chance.

He Love Me, He Love Me Not

Dear Bartender: So here is my situation: Yes at the local bar where my friends and I go all of the time I have a huge crush on the bartender! I know, I know avoid at all costs! However, he happens to be friends of my friends as well so he isn’t just some random bartender.

Anyway I let him know I was interested (getting drunk and giving him my number – I know mistake number 1!). I didn’t expect anything when I woke up the next day, I even felt a little dumb about seeing him again, but now every time I come in to his bar he hugs me, usually doesn’t charge me, tells me not to tip him and sometimes when I come to the bar to order a drink he will just lean over the bar to kiss me on my cheek! Even if the bar is packed he will take time out to talk to me or if I’m leaving, to leave the bar to give me a hug goodbye! And even when the bar is packed, I will look over at him and well catch each other’s eyes.

The other night when I came in he was just managing the bar so he wasn’t technically bartending. He came over and sat with me and talked to me all night. And we talked about real substantive things – like books, religion, etc. Then my friends were going to the store and I had mentioned I needed cigarettes and he just gave them money for them and asked my friends to buy them for me (he even knew what kind I smoked). When I was leaving he tried to get me to stay but I needed to wake up for work so I left. However, he hasn’t tried calling me or even asked me out.

I dated a bartender/bar owner for a long time so I get it: you’re a bartender. Your job is to flirt with pretty girls, make them come back, buy drinks etc. Girls try to hit on you all the time. But this time I think the guy may really be into me but I don’t know how to take it outside the bar where he works. I think he just takes for granted that he will see me at the bar at least once a week! Or maybe this is just an ego thing because I made it apparent I was into him? I’m not sure – am I confusing the signs? Is he just doing what a bartender should do? When is it bartender etiquette and when does the bartender ever like the girl?

Thanks,
Totally confused!

Dear ‘fused: You’re confused for a very good reason: this guy is doing everything he can think of to ‘fuse you. God knows what his agenda is but he’s sure not trying to be your boyfriend. Don’t tell him I told you, though, or those free drinks will disappear quicker than you can do a shot of Key Lime Pie.

He’s playing games. It’s his job. You know this already.

And, maybe I’m being too cynical here, but… that part about not tipping? He only means for you to tip him more subtly.

Don’t get me wrong. It’s not as if I or any other bartender hasn’t hit on a customer and meant it once or twice. It’s just that, when we do, you won’t have to ask if we’re serious.

24 & There’s So Much More

Dear Bartender: As a bartender this must be the most common thing you hear: I have been dating my girlfriend for 18 months. She will make the perfect wife/mother. She is very caring and loves me more than anyone else. But we are only 24. I feel the urge to have sex with other women as I want to experience all that life has to offer. I enjoy sex with my girlfriend but still want to fuck other women. My girlfriend is the jealous type and would never understand something like this. She would not believe that I could satisfy my sex drive with other women, while still being intimately in love with her. One day I want us to get married and have children. But I realize my sex drive will only last so long and do not want to regret it passing me by. I don’t want to be deceitful or hurt her. I don’t want to resent her. How do I reconcile sex and love?

Dear Wants It All: First things first. Your girlfriend is not the “jealous type.” The correct way to describe a girlfriend who doesn’t want her man fucking other women is “female.” You’re not the first man to have this problem.

Mother Nature designed men and women with the proliferation of the species in mind, not your personal satisfaction. Man is born wanting to spread his seed; woman is born seeking to secure a safe haven for her young. That these two things are in conflict is the reason Hollywood has produced an excess of romantic comedies.

In short, you want what every other male on the planet wants: to fuck around without consequence. Sadly, it don’t work that way — the occasional exceptions notwithstanding. (Many gay male couples — ones who have come to grips with evolutionary reality — have enduring relationships that are less than monogamous, to give one example.) It’s unlikely you’re going to get all the sex you want without going behind your gf’s back.

The alternative is to wait until she gets restless — it happens around age 35 — and broker a deal, tit for tat. But by that time, alas, your sex drive will be on the downhill side of Mount Everybody.

Mother Nature has a sick sense of humor.

What Would Miss Manners Say?

Dear Bartender: What is it about dating in NYC??? Recently, I was having a meaningful evening with a date and he spent the entire evening across the table, texting his friends. Don’t you think this is extremely RUDE! Oh, and the worst part was that we were having sex at the time. Thoughts?

Signed,

IM Sad

Dear Sad: The next time you’re having sex with someone, it would be useful to let him know. Send him a text, maybe. Or hit him on the head with your princess phone.

Some Questions Are Easy

Dear Bartender: Hi, I’m a 26 year old guy, with gf and also a daughter. I love to watch every type of porn… also gay porn and I get very horny. Now, I have a friend (straight with gf) who is 20 yr old… He is very cute and sexy and I really really fancy him. I wish to give him good blow job! When we are alone in the car we always speak about sex and girls… When we are on d net we always speak about sex and he often sends me porn pics. Sometimes he sends me pics and I start to jerk online … I tell him that I’m jerking and he continues send me pics. Also sometimes he start asking me questions about my sex relations and I know that he is jerking on the other side because he continues asking me to enter in details. He also tells me what his gf to do him in sex and also asks me abt my gf. We went abroad together and we slept near each other, and 1 time there was porn on tv and I started jerking in front of him. He started to mention to me the girls that I like and I told him to stop because I was going to cum but he continued to telling me hot things and also doing noises… He started to jerk too but not showing like me. For example I got nude in front of him out of shower and I noticed that he was looking to my cock… One time I came out of the shower with a hard cock and he continued to watch. Or I had my cock hard under the panties and I received a telephone call… He was near me and he hit with his hand (joking??) my hard cock. But he never showed me his…

Every night we text each other and last night I told him that I’m not going to wrk anymore with him…and he told me that he is going to miss me etc.

I’m very confused abt my and his feelings and what should I do!

Dear Confused: You should suck his dick. Duh. Don’t worry if it will make you gay. You already wear panties and use “fancy” as a verb. I’d say at this point you’re in a free-fall.

Ladies Loving Ladies

Dear Bartender: What’s the current word on ladies who come into the bar, get a little drunk and start making out? They’re not lesbians, they just like to make out when they’re drinking. Is it considered dumb by the bartenders? Passe??? Is it excusable behavior? Should said ladies stay out of the bar for a while? Do bartenders always remember the silly behavior of the patrons??

Thanks.

PDA Problems

Dear PDA: Why do you care so much about what the bartenders think? Bartenders have more to worry about than who kisses whom after a few dozen cocktails. Frankly, when women come into my bar, I’m happy if they’re kissing and not pulling each other’s hair. I’ve seen women drunk, I know what I’m talking about.

Playing With Fire

Dear Bartender: My fianceé is a bartender in a local bar in her home town. She has been there for 6 years and has quite a few regulars, most of whom go there only looking to score with her.

She was married when I met her, and it hit me when I went in there one night with friends that she was quite miserable being married, only she had two kids with the guy and didn’t want to leave him if she couldn’t find anything better. So anyhow, here I come, and we immediately fall in love and are engaged a year and a half later.

She loves me going up there when she works, and I have every night since we met to help her close it up and clean up since the managers leave no one behind when she closes.

Anyhow, she is not the most beautiful woman I’ve dated, but every time I am there someone is hitting on her, and some guys do it for months at a time. I know she is working for tips, but the thought is I know she cheated on her ex so I worry she would do the same to me.

She isn’t, but I can’t help but have the jealousy feeling, and I get angry at the guys that come in there after her and tell her that one night with them and she’ll never go back. Sorry for filling your page. But what do you recommend for me to get over that jealous feeling? Anything?

will-ohio

Dear Will: Uh, the time to wonder if this woman is OK with being married and sleeping with her customers was when she was married and sleeping with you. That sounds harsh, but you gotta admit it’s a little late in the game to be asking that question.

I’m not saying she’ll cheat on you. There’s no way to know if any woman will treat all of her husbands the same. For all I know your jealous rages turn her on, and that’s what she was missing from every husband up till now.

Still, getting married is not unlike jumping out of a plane, with trust being the parachute. You can do it without the parachute, but perhaps it’s smarter not to jump.

S.O.S.

Dear Bartender: So I spent an hour today forcing my toddlers to slow-dance with me to Todd Rundgren’s Hello It’s Me on youtube. Translation: Midlife crisis.

What do you recommend? No affairs, mind you, or fancy new purchases. I love my husband, and we’re on a budget.

Dear Crisis: You’re getting ahead of yourself. When you have your real mid-life crisis, someday, little things like loving your husband and having no money will be no obstacle whatsoever to that affair or fancy new purchase.

Sister, you ain’t seen nothing yet.

Don’t touch me there

Dear Bartender: I have an unhealthy (I think) penchant for rubbing up against others. What do you call that? I get a wonderful thrill “accidentally” making contact with strangers on a train and bumping into people in a crowded bar. Is this okay?

–Rub-a-Dub-Dub

Dear Rub: You, my dear, are a 302.89, a frotteur. Frotteurism is different from frottage in that the first (your kind) is non-consensual. More casually called “groping,” you might find that this is a criminal offense, if only (usually) a misdemeanor.

I’m always happy to champion sexual deviancy. Priority is given, however, to deviancies that involve consenting adults. I don’t know if your “accidents” involve minors, but as they involve unwitting participants I will instead just tell you to get a grip.

Uh, let me re-phrase that: Rub-a-dub-dub, control yourself.

The Other Woman, Pt Infinity

Dear Bartender: Here’s the deal. Are you ready for this? My husband has a mistress. That’s not the problem. I’ve been braced for my husband taking a lover since my mother sat me down thirty years ago and told me this would happen. I accepted it long ago. What I wasn’t prepared for, however, was the bitch being uglier than me.

I am fifty-five. This woman — this THING — is sixty if she’s a day. It’s possible she’s fifty-nine but either way I’m wondering if I should be insulted that my man would take such an unattractive lover as an alternative to — of all things — me: a woman who likes to think of herself as reasonably well preserved.

What, if anything, am I missing?

— Wifey

Dear Daughter: Your mother was right to warn you this might happen. But she neglected to fill in the particulars.

The middle-aged man who strays — assuming he is otherwise reasonably happily married — is not selecting his mistress with the intention of insulting his wife. Your husband does not want to be found out, presumably, so how could he have chosen this woman specifically to insult you? Your husband was vulnerable to this woman’s charms — and I don’t care, since you were about to ask, if he approached her or she approached him. Men of a certain age are vulnerable; woman are vulnerable their whole lives, you’re used to it, so don’t assume you know what it’s like to have such a state surprise you just when you think you have your world under control.

Your decision now is whether you want to wait it out or leave him. You could, of course, confront him on the affair — but be careful: any sane man, given the choice, will pick the woman who has humiliated him less.

Comeuppance See Me Sometime

Dear Bartender: I am currently doing research for a paper about the industry’s wealth of incompetent and/or sexually deviant bar owners, and am finding it hard to see how people who are putting up with a bad bar owner can act, other than quit. I work for an asshole, someone with little experience in the field, who has just gotten a divorce, and who is trying to bring the place down as fast as he’s falling, and don’t know what I can do, other than harm the other bartenders at the place who rely on their jobs for rent.

Have you any stories about bad bar owners who have received their comeuppance? I haven’t heard of it yet…

PS, love the site, you’re providing a necessary service.

–Nick

Dear Nick: Bad bar owners who’ve found their comeuppance are like unicorns: we’ve all heard of them, but dernit if we’ve ever seen one in person. Bar managers are even worse. I’ve endured a few. Does the stress of owning a bar make bar owners crazy? Or do only crazy people open bars?

Alas, as far as I know, you can either endure them, or quit.

But it’s this paper of your that fascinates me. I love how you’ve married incompetence and sexual deviance. Is there a connection between the two that I never knew about? And what compels these sexually deviant/incompetent people to open up bars? What kind of research are you doing? How bad is your boss? What’s his sexual deviance??

Don’t leave us hanging, Nick. Tell us more!

Return to Sender

Dear Bartender: If someone tells me my dog is cute, do I have to tell them that their dog is cute, too? I feel stupid, even if their dog is cute. But then again I don’t want to say something even stupider like “Oh, and your dog has good posture” or “Guess you’re pretty happy with his breath.”

My dog happens to be very cute so this happens all the time.

Dear Girl with Cute Dog: No, you don’t have to return the compliment. Just say “Thanks.” If you must say more, just ask for the name.

This also would work when someone tells you you’re a good lay. I’m just saying.