Dating Your Boss, Money, and Finding Guys Like Dave Bry

So, I've just stepped into the big, bad corporate world. It's been about three months and guess what, I'm already craaaazy about my boss. It started out as a little crush, and now it's this full blown romance-but-not-romance thing. Ahem! After one night of staying back a little too late, we ended up making out. A LOT. And, it was so good. I mean, the kind of mad kisses you see in movies. We talked about it and how I felt horrible (and not to mention, incredibly YAY, but I couldn't tell him that) about doing this with my boss. He said he felt really guilty, and that we'd have to stop. Which … ummm, how do I say this, did not happen. At all. The making out hasn't stopped. We've been going out to these cute little dinners and sharing our life stories. Also, we've been stealing kisses at work (which is SO wrong, but feels SO good!).

We've had a few of these it's-wrong-to-do-it-we-need-to-stop conversations, but nothing seems to come out of it. Work-wise, he's not been treating me any different than he does the others, which is something I appreciate. I don't want any special favors because of the being-busy-with-each-other on the side bit. But, god, he is SO great. And intelligent and funny and all of those things. I have no idea where to go with this. Also, one tiny thing I left out, he's 30 and I'm 21 … that seems to be an issue with him. Because apparently, I have a lot to see/learn/do/blah, and he doesn't want to be the one coming in the way. I want to be with him, and in spite of confessing that we're falling for each other, nothing seems to be coming out of it. What am I supposed to do?!

Fuck him in his office. I mean, congratulations, you’re in a hot office romance, and not a lot of people get that opportunity. Plus, it’s not just a co-worker, it’s your boss. These are the things that porn movie plots are made of! Boring couples role-play this shit, you get to do it for real. So either wait until nobody's around, or the two of you come by after hours to smoke a joint on the roof, and then play some cheesy sex music on his office computer and let him bend you over the desk. It will be a night you play over in your head the rest of your life.

Also, you’re going to have to quit your job. Maybe not immediately, but eventually. There are so many bad ways this can end and quitting is the most humane. The worst way it can end, for him, is that you sue him and his company. This is most certainly part of the danger calculus that’s going on in his head. You are a liability to his career. And at 30, that’s when most guys start taking that sort of thing seriously. Welcome to the corporate world.

The worst way it can end, for you, is that he finally gets freaked out to the point that he shuts the whole thing down and you still have feelings for him. Because then your workplace life will be miserable. Distance is one of the essential ingredients for moving through a breakup, and obviously if you have to go to work every day and answer phones or file paperwork or take orders from the guy who broke your heart, it’s just not going to be healthy for you. You’re going to want to quit.

“But, Ask a Dude Guy, didn’t you read where I said we’re falling for each other? Why are you so sure we’ll break up?” Because you’re 21. The reason that’s an issue for him is that he was 21 once, and he knows that the first couple years after college basically consist of wandering through a forest looking for your identity. You’ve got a lot of twists and turns before you’re capable of the stability and self-awareness he’s looking for in a partner. Somewhere between now and 28 (the mean seems to be 25 these days) you’ll come to a point where you suddenly Take Control of Your Life, which is kind of a molting thing, and he doesn’t want to be cast off as as part of the old life you shed just when he’s ready to start thinking about kids and houses and stuff. If he’s smart, he’s going to fight every urge to fall in love with you.

But yeah, fuck him in his office. The story you take away from that, it will be the best severance package you ever get.

Just about a year ago Dave Bry wrote that apology to his wife on The Awl. So honest and sweet! But … how can a girl tell the difference between guys who will one day have the capacity to write letters like that and the guys who will only continue to care about getting high and their fantasy baseball draft? Any thoughts on the topic/litmus tests are greatly appreciated!

OK, there’s absolutely no correlation between Fantasy Baseball and emotional availability. In fact, a passion for Fantasy Baseball should be regarded as a good thing — it shows that your guy is capable of real commitment. The amount of devotion you need to manage your team every single day during the course of the regular season, that’s not something just anyone can muster. You have to deal with ups and downs, with unexpected setbacks, and you need to know your players intimately to judge whether they’re going through a slump or if there’s a more serious problem that needs to be addressed. These are relationship skills.

The only test of whether your guy is capable of insight, self-reflection, and spontaneous emotional expression is whether he already does stuff that proves it. At six years old I would walk home from summer camp and pick flowers for my mom along the way. At thirty I do the same thing for my girlfriend. I know, I’m kind of a pussy. But my point is that certain things are innate, and if you want a guy who's comfortable with his vulnerability, then it’s pretty easy to tell when you’ve found him because he has a track record.

By the way, the other side of the emotional availability coin is just as annoying. Guys who constantly put it out there come off as needy and may drive you insane. And it’s probably easier to crack a guy open than it is to shut him up. If you want your guy to express himself more, you can certainly coax it out of him. But if you’re looking for someone who naturally has the exact right balance, like how you imagine Dave Bry to be, know that there are not many out there. Most people are either too open or not open enough. Pick your poison.

Also, tell your guy to pick James Loney. I’m betting on a career year.

I've been dating a guy for five months. He's very intelligent, driven, successful, athletic, and interesting — all qualities that I've always wanted in a guy. The problem is, he tends to snap at me when he gets upset, which is usually over money issues. He blames his sensitivity to money on past girlfriends who he felt took advantage of him. He makes at least three times my salary, and I have enough disposable income to spend traveling 1.5 hours to see him every other week and go on dates, because we split almost everything.

He also snaps on me when he feels upset about something, and doesn't let it out in the right way. Instead of talking about something calmly, it's suddenly "Fuck you," leaving me blind-sided and really hurt.

Last time it happened, it was because he paid for his own meal and my beer, and I didn't say "Thank you," so he blew up at me, calling me selfish and inconsiderate for expecting him to pay for it. The first blow-up was over an incident that occurred weeks beforehand, which he'd apparently been stewing over. He suddenly cursed me out in a situation where I had no control, and he wouldn't let me leave. It was quite scary, actually.

After both arguments, we talked and he apologized and promised it won't happen again, and he'll do whatever it takes to make me feel safe and happy. I wanted to believe he was genuine and really didn't mean to hurt me after the first time, but I have reason now to believe that he's just talking out of his ass, because he knows he shouldn't treat his girlfriend that way, and he says he "loves" me.

I don't want to be disillusioned by this guy, or glaze over his negative qualities for the sake of the good ones. We almost broke up once before after the first blow-up, and I sometimes think I should've stuck to my guns at the time.

I just can't tolerate a guy who can't stand spending a dollar on me unless I thank him profusely immediately, lest he get aggravated later and lose his temper again. I don't want the next step to be a physical smackdown instead of a verbal one.

Am I overexaggerating, or should I really be that sensitive about who pays for what? Shouldn't a boyfriend not take issue with buying his girlfriend a drink when they sit down to eat, especially if he has plenty of money? Or is it wrong of me to assume that he should pay for anything at all? I'm not a gold digger and I'm not unappreciative.

Here the kicker too — the day after the beer/money issue, he takes me out, and I of course offer to split the bill — and he says sheepishly, "You don't have to be sensitive about this stuff now." Well, yes I do, because it obviously is a problem for him.

First, the good news. Of all the baggage you can take from one relationship to the next, money issues are some of the easier ones to navigate. The best way for a poor girl to date a rich guy is to take him out once in a while, and to make it clear from the beginning that you’re taking him out and you don’t want to hear about it, and then take him someplace you can afford. Like a taco truck or the movies. Also, you can insist on paying when you guys happen to go to Starbucks together or other small little expenses like that. Because when two people have unequal incomes, it’s really the effort that’s important, not the actual splitting down the middle. If you pay what you can afford, he will notice that and appreciate it.

The way I figured this out, by the way, is I dated a girl who didn't make a lot of money but had a ton of pride, and she paid for every little thing she could. A dollar-fifty taco from her was worth more than any hundred dollar dinner I ever bought her.

Now the bad news. Money is the least of your problems. Your guy sounds pretty damaged by past girlfriends, and this thing might be just a reminder of bigger pains that haven’t quite healed yet. It happens to the best of us, even intelligent, athletic, driven potential husband types. The way he snaps at you, that’s a red flag with “I’m not ready” (and also "I'm a potentially dangerous and violent asshole") written all over it.

The way I know this, by the way — the "I'm not ready" part, not the "potentially dangerous" part — is that the girl who bought me tacos left me kind of wounded, and the next girl I dated never offered to pay for anything. And man, emotions came out all kinds of sideways.

Also, what’s up with this 90-minute commute to see him only once every two weeks? Maybe you’re both trying too hard to move forward.

OK, so I can't put too much precise information in here because I have friends who read this and they'll know. But safe to say my partner is going through some horrible stuff right now — like, seriously horrible, I'd-be-having-a-breakdown-and-sobbing-on-the-floor kind of horrible stuff. He's pulled away from me (and everyone else), is becoming quite short tempered and snide, and being far less caring and affectionate than when all this shit started.

The problem is, when I ask if he's OK or about his problems he talks as if it's fine, and doesn't seem to think there's a connection between his behaviour and what's going on in his personal life. Obviously if I didn't know what was going on I'd have kicked this guy to the curb because I'm not on to dally about with someone being inattentive, introverted, and snarky — but on the other hand, I can totally understand where it's coming from and so can forgive him for it. The problem is, it's starting to make me unhappy to be around him or be wondering what's going on and what kind of person he's going to be today.

So my question to you, O Dude, is this: How do I talk about this with him? I know it needs to be discussed, and I don't want to put it off, but I don't know what to say.

Grief sucks. It sucks for the person grieving, and it sucks for the people who care about him. Someone who’s Going Through Something generally has a window of a couple months where they can lean heavily on their close friends, but once this period is over they really need a set of recovery tools that they can use on their own. Therapy is essential. Going to the gym or jogging or learning to fight is incredibly helpful. Reducing his intake of drugs, alcohol, and cigarettes is also a good idea. He can always go back to those when he feels better!

So the first question to you, O Reader, is this: is your partner doing things to help himself? If he’s not, that’s the perfect place to begin the conversation. “Listen. You need to be proactive about your mental health. I need you to be proactive about your mental health.” If he won’t talk to a therapist, then there’s not a lot you can do. I’ve put undue strain on two relationships because I wouldn’t, for whatever reason, go talk to someone. It wasn’t fair to either girlfriend.

If he is taking steps to help himself, then you need to ask yourself whether you can ride out the rough waters with him, which can take a long time. It will require patience. It will be taxing. I can’t tell from your question how invested you are in this relationship, but if this is too much too fast or things were never really that serious, you might not have the willpower to deal with it. If that’s the case, you need to be completely honest with him. It’s a healthy thing to know your own boundaries. And yes, you will probably feel like an asshole. But you’re not. As Bono says in that old U2 song, 'I can't keep holding on to what you've got, when all you've got is hurt.'"

Now, if you're willing to be there by his side while he proactively manages his grief, then may the wind be at your back. Remind him periodically that you’re there for him. Distract him, try to make him laugh. Steel yourself against his outbursts. And just keep talking. Grief hits everybody at some point, and probably more than once. Having someone who loves you nearby makes it easier to deal with.

Previously: Workplace Drama, Idiotic Nicknames, and the Butterface.

A Dude is one of several rotating dudes who know everything. Do you have any questions for A Dude?

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