Tag Archives: significant other

Work is fun because I meet boys there!

“Bob” and I dated for a while, and now “Tom” and I are dating. The breakup with Bob was mutual; Tom and I are having a great time getting to know each other. The problem is that we all work together, and I think Bob is starting to have some bad feelings about me dating Tom. I don’t know if he’s jealous, or territorial, or what, but I do like him and want him to be happy. Should I have said something to Bob before Tom and I made our relationship public? Did I breach some protocol here?

You’re allowed to date any man you please, but that’s not the problem here.

Stop dating people from work. I’m all for office romances; they’ve produced some of the most delightful couples I know. But your office isn’t your own personal dating service; the break room isn’t a pickup joint. I know it’s not fair, and it’s not right, and it shouldn’t be this way, but a woman taking the part of the company Casanova is not going to do the same things for your career that it might for a guy. It’s easy to get another boyfriend, but not so much another job.

Your private life is your business, but the minute you start skipping through the office halls holding hands with the second guy as many weeks, you might want to reconsider. If you think Tom is the love of your life, then fine, go for it. Don’t worry, Bob will get over it. But if it doesn’t work out, no more fishing in the company pond. No more.

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I don’t have enough problems, so I’m just going to make them up.

I’m in my 30s and have been dating a guy who’s in his mid-twenties. We’re having a great time, we get along very well, and he’s a nice refreshing change from my past relationships. The problem is that I can’t just enjoy it for what it is, and I can’t stop thinking about the fact that it seems inappropriate to be dating him. I don’t know what’s going to happen in the future, and I don’t know how serious I am about this long-term. But I don’t want to ask him because I don’t want to either hurt his feelings if I’m not serious enough, or scare him away if it seems like I want to get married. Should I just break up with him and move on?

Yes. Dating a fun, young, attractive man is a really bad idea. I think you should break up with him and go find a guy in his fifties who has three teenagers who hate you and an ex-wife who wishes you were dead.

Having fun when you’re dating is just wrong, so I’m glad you’re spending your time worrying about whether you like him too much or not enough, and that you’re going to sit him down for a conversation about where your relationship is headed even though you don’t really care. I’m sure that while you’re spending your free time fretting over what it all means, he’s at home doing the same thing. I’m sure he’s not watching TV with his hand down the front of his pants, or golfing with his friends and talking about the Celtics, or doing whatever else it is that normal, functional people do.


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Outgoing people, married people, and people on Prozac are all like this.

I’m shy and my boyfriend isn’t. He’s isn’t mean about it but he’s always encouraging (pushing) me to come out of my shell etc. and I’m just tired of having this conversation. I am never going to strike up a conversation with strangers, be 100% comfortable talking to people I just met, or walk into a party and announce my arrival. So I’m a little quiet. I like my shell. Is there anything wrong with that?

The next time you go out, wear a boobalicious top and hot pants. When you walk into the room, jump up and down and yell, “Yoo-hoo, Judy’s here, and I’m wearing my party panties!”

Then drink too much, and talk to anyone who comes within a 10-foot radius. Loudly repeat limericks that involve the word “Nantucket” and tell jokes that involve Playboy bunnies, a cucumber, and a desert island.

By the end of the night I’m sure he’ll be desperately wishing you were back in your shell.

(Or, next time he tries to tell you to come out of your shell, just holler, “HOW’S THIS? SHUT THE HELL UP!”)

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My sister’s boyfriend is a douchebag.

My sister is dating someone I absolutely cannot stand.  They live in another state so it’s hard to judge how happy she is in the day-to-day relationship.  When I ask how serious she is about this guy – she admits she is not sure.  How much leeway do I have to say, “You’re dating a douchebag”? I don’t want them to get married and have that come back to haunt me or drive a wedge between me and my sister.  Do I have to just shut up and deal with this chump?  He is rude to our parents, bossy, controlling and generally unpleasant.  I am not the only one in my family with this opinion.  I know I should be thinking about HER happiness… but what about meeeeeeeeeee (and honestly how can she be happy with this guy)?

Hire a prostitute to seduce him, have a handsome and sensitive private investigator videotape it, and then have the P.I. show it to your sister so she won’t have to know you’re the one who hired him. She’ll see the tape, be angry at the boyfriend, and the P.I. will comfort her. They’ll fall passionately in love and during their wedding toast you can reveal that you hired the prostitute, and since she’s so happy, she’ll forgive you and you can dance the last dance of the night with the hot P.I.’s hot brother.

This will totally happen. Or else this is the plot of a movie I saw last weekend on Lifetime.

Anyway, here, in short, are your answers:

1. You have no leeway. She’s your sister, not your alter-ego. You know the old saying…one girl’s douche is another girl’s treasure.

2. Yes, you have to deal with this chump, but no, you don’t have to shut up. I recommend the sneaky route. Fan the flames of your parents’ hatred of him. If they complain about the boyfriend, use every opportunity to say, “You know, you should really say something to him next time he’s rude to you.”

3. What about you? YOU are going to be a nice, supportive, sweet sister. You’re going to do what you can to make her realize her full dating potential without her knowing. Talk her up, make her feel good, listen quietly when she complains about her boyfriend, and have faith that in good time a girl as awesome as she is will realize there are too many great guys out there to be dating a crappy one.


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Babies? Eh.

I’ve always assumed that I would have kids. As I get closer to that reality I realize I am secretly worried I’m going to wreck them or, worse, hate them and be stuck with them forever. That doesn’t seem maternal, does it? I haven’t told my fiance this because it would make him freak out. Is this normal or something I should investigate further (possibly with the help of a trained professional)?

Think of the biggest asshole you lived with in college. The one who peed the bed, had loud friends over, threw her dirty clothes all over the place, had severe boundary issues, and thought the floor was an acceptable place to keep unwrapped food. Imagine this every day for the next 18 years. There. That’s what it’s like to have a kid. They can be assholes.

It’s possible you’ll hate them on occasion, but unless you’ve been diagnosed with attachment disorder, I’m sure you’ll love them, too. I’m also sure you’re going to wreck them, but whatever. Everybody does that. No one is ever “ready” to have kids; until they’re here and there’s no turning back, you’re going to be scared shitless. And then you’ll continue to be so for the rest of your life.

If you really don’t want babies, though, you need to tell your fiancé. It’s profoundly unfair to marry someone who definitely wants children when you’re not sure you want them yourself. Being unsure means you could go either way; he seems like he’s already decided.

Therapy can’t make you want to have kids, but it could help you figure out why you’re so scared of wrecking yours. It could also help you figure out why you think you’re ready to spend the rest of your life with someone when you can’t even tell him something REALLY SIGNIFICANT like that fact that you might not want kids. Not having children isn’t a big deal–tons of people don’t have them and are deliriously happy. Pretending you want them in order to please someone, though, is a big deal.

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Ms. Jackson if you’re nasty. Or, Ms. Jackson-Smith. Oh, okay, fine. Mrs. Smith.

I’ve been dating my boyfriend for around six months and things are going really well. This last weekend we were at brunch with some of his friends when the topic of women changing their last names came up — and my sweet, understanding boyfriend suddenly announced that not changing a last name was a “deal-breaker” in his his eyes. Yikes! I’m not 100% certain I want to change or not change mine, but I’m alarmed by his hard-line approach here. Should I be scared?

I married one of those self-important blowhards. (Sorry, honey. Love you!) He also announced that not changing my name would be a “deal-breaker,” but lucky for him, he did so after we’d already gotten married and I’d already changed my name. Had he made this freaking ridiculous announcement before our wedding, I’m fairly sure I would have not changed my name. (I’m also fairly sure he still would have married me, but who knows, really…)

Only be scared if he’s also this bossy and unattractively un-feminist in the rest of your relationship. Beware if he expects you to: cook dinner for him every night, wear a skirt every day, always be skinny, not yell, call him “Sir,” comb your hair on a daily basis, do all the housework, or always let him have the remote.

For now, just tell him, “I haven’t decided if I’m going to change my name when I get married, but my future husband’s opinion sure as hell won’t be the deciding factor. So if it really is a deal-breaker–and only you really know the answer to that–we might as well save the trouble and split up now.”

Don’t make a promise you’re not totally comfortable keeping. Setting that precedent so early in a relationship is only going to make it harder to assert yourself later, when it’s something you actually care about.

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My fiancée’s friends hate me. For good reason.

I recently cheated on my fiancée on a business trip. It was one time, I was drinking, and I feel terrible about it. She has forgiven me and the wedding is back on track, but my problem is her friends. They hate me now. How can I convince them that I’m sorry and it won’t happen again? It’s causing my fiancée a lot of unhappiness because of the tension with her friends.

I’m not happy with you, and it’s not for the reason you think.

If your fiancée wants to forgive you getting jacked up and hooking up with some boozy hussy from Topeka, that’s her decision. But I have a problem with you just coming back, ‘fessing up, and then fretting about the fact that her friends don’t like you. It’s not fair to the poor girl to claim you’re ready for a wedding.

People who are mature, happy, in love, and ready to commit know that they should keep their body parts to themselves. In fact, they WANT to keep their body parts to themselves. Or at least to themselves and one other person. That person being their betrothed.

I don’t think you should be engaged at all, but if you’re too much of a wuss to put things on hold, you better figure out what’s wrong with you ASAP. Go to therapy, read some self-help books, take up yoga and meditation, stop drinking on business trips, and stop having sex with other people. Concentrate on making yourself a good, honest man who knows how to be in a committed relationship. Once you prove this to your fiancée, you can worry about her friends.

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I think my boyfriend secretly wants to make out with my mom.

I think my boyfriend is flirting with my mom and it’s freaking me out. Sometimes they even email each other, and it makes me jealous. He’s naturally flirty, though, and my mom loves attention, so maybe I’m just reading into it. On the other hand, it’s not like we’re kids. My boyfriend and I are in our 30s and my mom is on the young side. They should both know better. Should I say something?

Let’s start with your boyfriend, since he’s easier to deal with. (I’m going to assume that you’re not normally the jealous type who flips out and wants to tear a girl’s hair out for accidentally looking at your boyfriend.)

Something he’s doing is skeeving you out, and he should stop. So it’s perfectly reasonable to say, “It makes me uncomfortable when you tell my mom her ass looks good in those pants.” Or, “I don’t like it when you lick your ice cream cone that way and then wiggle your eyebrows at my mother.” Or whatever specific thing he’s doing that suggests he’s flirting.

If he’s nice and understanding about it, and reassures you that he’s only saying those things and emailing her because he loves YOU and just wants to get on her good side for YOUR sake, then great. If he flips out and accuses you of being ridiculous or paranoid or controlling or jealous, you might want to think for a second about this: he’s a douche bag, he doesn’t care about your feelings, he’s being wildly inappropriate, and you should break up with him.

As far as your mom is concerned, you can’t really get rid of her. So do one of the following: 1.) Be passive-aggressive and make a joke about it, then glare at her and hope she gets the point and knocks it off. 2.) Don’t say anything, swallow your anger and resentment, and eventually when your head explodes and you have to go into therapy, talk about it there. 3.) Be firm but gentle. Tell her you don’t like it when she makes kitty claws and meows at him, or asks him if he’ll rub suntan lotion on her back and says, “I wish my boobs were on my back.” And whatever her response to you is, just be pleasant and ignore any insistence that it’s all in your head.


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