Lonely in the Tundra

Dear Mistress Maeve,

The close of another year … alone. I am a rapidly-turning-40 dude who's never been married, not even close. In my twenties, I thought I had so much time. In my thirties, I spent too much time chasing my twenties (and the women to match). Now, here I am — the only single guy out of all my friends. I spend most evening with frozen pizza and Netflix. Just about the only interaction with women I get is through my Xbox. I don't ski. I don't bike. I have a beer gut. Yet I live in Vermont — where you can't meet a girl unless you bump into her at a sporting-goods store or hiking fucking Camel's Hump.

Do I really have to give up living in this beautiful land and move to a city in order to find a woman who doesn't own a pair of Sorels?

Signed,
Lonely in the Tundra

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Dear Lonely,

Sorry to break it to you, but any Vermont woman who doesn't own a pair of snow boots is an idiot. However, that doesn't mean you can't find a girl who's willing to swap her Sorels for stilettos, given a proper invitation.

Last time I checked, no eligible ladies were hanging out around your pity pot, so get off it. Your failure to rock climb and backcountry snowboard may make dating more difficult, but you just have to get creative. What type of woman are you looking for? Perhaps you'll meet her at an art class, at the comic shop, or sitting at a table at Muddy Waters? If you're still attached to staying on your couch, give online dating a whirl. I guarantee, you'll find plenty of Vermont women who would prefer a night on the town to a day on the mountain.

And, hey, if all else fails, you're just a short drive from Montréal — a city bustling with metropolitan ladies.

Happy New Year,
MM

Rubbing Her the Wrong Way

Dear Mistress Maeve,

My partner and I (she's a woman; I'm a man) are each 60, have been together four years, and have the best sex of our lives together. Recently we were staying in a motel and, after an extraordinary session of love making, I woke up at 3:30 in the morning with insomnia. Our sex should have knocked me out for the night, but it didn't, and I soon started replaying our earlier love making in my head. I was aroused. Rather than wake my lovely partner, who needs more sleep than I do, I began to quietly masturbate — but it wasn't quiet enough. It woke her, and besides being annoyed to be woken, she was upset, believing that my masturbating meant her love making wasn't good enough for me.

We talked about it the next day, and I told her she had nothing to worry about. I told her that just thinking about her excites me and makes me so happy and satisfied that I rarely masturbate, but that men and women are different. Maybe a woman masturbating during a relationship can reflect some dissatisfaction, especially if it's done regularly. Maybe it's the same with a man, too, for that matter.

We enjoy your column, so I offered to write to you for your take on this matter.

Signed,
Essex Wanker (rarely!)

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Dear Wanker,

News flash! Guys, if you think you can masturbate next to your sleeping beauty and not wake her, get real! Unless she's had a bottle of Chardonnay and two Advil PM tablets, the subtle shaking of the entire bed and the suctioned slapping sound of you jerking it are sure to rouse her from slumber. If you must tend to business, please, head for the bathroom.

Now that we've got that squared away, let's move on to your inquiry. As long as you are still interested in sex with your partner — which you clearly are — masturbating is a healthy activity. Your sexual relationship with yourself is just as important as your sexual relationship with your partner. Through masturbation, we learn which sensations feel good to us, and we're able to play out fantasies in our minds that fuel the continued intimacy with our partners. Your lady has nothing to worry about. In fact, she should be thrilled to have a sexually charged partner who worships her so.

One last thing: Forget the gender bias in your talks about masturbation. Men and women enjoy pleasure equally, and the idea that men should get off more just encourages old ways of thinking about women and sex.

Touchingly yours,
MM

Not Aural About Oral

Dear Mistress Maeve,

I have been sleeping with a guy for a few months now. I think that we connect and have great sexual chemistry, but there is something missing.

In the beginning, we would just have fast and rushed sex, but as time went on and we realized our encounters were going to keep happening, more foreplay became involved. So I have performed oral sex on him several times now and he has YET to go down on me. I'm really into that and I would really like it to happen, but I don't know how to approach the topic. I don't feel comfortable enough in the heat of the moment to just ask him to do it and I don't know if he has any weird reservations about it. So I don't know what to do. What gives?

Signed,
Oral, Not Aural

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Dear Oral, Not Aural,

Let me ask you a question: If you stopped going down on him, how long do you think it would take him to inquire about your sudden suspension of services? My guess is probably not long, so why are you being bashful about asking him to please you?

If you can't bring it up in the heat of the moment, give it the pillow-talk treatment. Talking about our desires and making requests of our lovers is sometimes best received while basking in the glow of a successful romp. Start by complimenting him on the areas of lovemaking where he excels, then just come out and ask him: I've noticed you've never made a move to go down on me -- how do you feel about giving oral? You may discover he has hang-ups, or you may learn he was simply waiting for you to guide him.

I don't care when and how you talk to him about it, but you MUST talk to him about it. Asking him for what you want is as much of a lesson for you in communication as it is a lesson for him in reciprocation.

Sweet and lowdown,
MM

Exed Out

Dear Mistress Maeve,

Last week you responded to a woman who was concerned about her boyfriend's relationship with his ex. Well, I'm in a similar situation, except I'm the guy in the scenario.

I'm dating this phenomenal woman, and I have nothing but the best of intentions with her. While I don't run errands for my ex or help her with household finances, we do hang out a couple times a month (happy-hour drinks or lunch). My new girlfriend has recently expressed her dislike of my relationship with my ex and has asked me to stop hanging out with her. I told her I thought it was ridiculous for her to ask me to stop hanging out with a friend. She said that it was "obvious" my ex is still into me. I don't see it.

I haven't hung out with my ex since this talk with my girlfriend, but I don't feel good about it. Can't exes be friends as long as certain lines are not crossed?

Signed,
Ex-isting Relationship

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Dear Ex-isting,

Relationships with exes are complicated. Some people can have pleasant, nonthreatening friendships with past lovers, while others can't get near their exes for fear of being arrested or committed. Many of us fall somewhere in between with former flames, and what happens in this gray area can cause problems in our current relationships.

The bottom line: It's not OK for your girlfriend to dictate whom you can and cannot hang out with. That said, she has to be able to trust your decision-making fully when it comes to your ex.
Who broke up with whom? If you broke it off with your ex and she still wants to spend time with you, she may be pining for you. Be certain you're navigating this friendship with your eyes wide open. It feels good to spend time with people who admire us (and want to sleep with us), but you must be careful not to take advantage of your ex's vulnerabilities just to feed your ego.

But, hey, if you're 100 percent certain your friendship is on the up and up, it's time to reopen the conversation with your girlfriend. Let her know that, while you understand her concerns, you're not willing to ditch a friend over unfounded jealousy. Kindly remind her that a good relationship is built on trust, and you expect her to extend you some.

Exed out,
MM

Perplexed By Ex

Dear Mistress Maeve,

I've been dating a guy for about a month. I'm a total commitment-phobe, so I'm shocked to feel giddy and optimistic over this guy. We just "click," as they say.

I'm liking everything he's bringing to the table, except for one thing. I can't quite wrap my mind around his relationship with his ex. From what I gather, they were together about a year before she dumped him (not his choice to leave). Since then, he has continued to help her with household projects and errands when her car is in the shop. I initially thought this was just him being nice, but I recently found out that he paid a utility bill for her when she was unable to make a payment. Uh, really? If we're going to be in a relationship, that's just too much.

All these things put together are raising some major red flags for me. Not having had many relationships, I have no idea what the rules are for how exes should interact.

Thanks for the advice,
Perplexed by Ex

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Dear Perplexed,

Unfortunately, you won't find a rule book for dealing with exes. However, you already have your best reference guide: your gut. If your psychic receptors are telling you that he's not finished with his ex, you're probably right.

It sounds like his ex no longer wanted the responsibility of being in a relationship but still wants to reap the benefits of having a boyfriend. Hey, as long as he's willing to be her whipping boy, why should she stop using him?

Before you commit further to this guy, have a conversation with him about his ex. As uncomfortable as it may be, you must be honest about your feelings. While some people have no problem with partners who remain close to exes, he has clearly crossed a line for you by paying one of her bills, and it's important that you let him know that. Tell him that, while you appreciate his kindness toward his ex, if he wants to be in a relationship with you, he'll need to work with you to find an agreeable level of interaction with her.

Hear what he has to say for himself. If you're still seeing red flags, it may be time to back off a bit. Perhaps if he sees what he's missing, he'll stop being his ex’s doormat.

Committed,
MM