Dear Jackie,

You are a nice girl with a good heart, but I honestly couldn’t stand being your boyfriend anymore. You will probably never read this, but I think you deserve an explanation. Here are the REAL reasons I broke up with you last month:

1. I am not your therapist. You would think the hourly calls to your sisters would give you your fix. Please understand, guys just don’t do this. I really don’t need to hear about your sister’s annual physical. I have no vested interest in your mom’s apple pie recipe. Your office politics are important, yes, but I think an update once per month would be enough. And the stories about the transsexual guys your gay roommate brings back to your place kind of turn my stomach.

2. At age 27, there has to be more to you than what shoes to wear with what outfit. Sleeping in until the moment you leave for work, then getting drunk every night the moment you leave work, while it might seem to be extremely relaxing, is not really a very inspiring way to live your life.

3. Your apartment is disgusting. I hate to be blunt, but I gave up the “college dorm” scene when I left my college dorm. One bathroom for a house full of roommates and their fuck buddies is more than enough to churn anyone’s stomach. And the fact that you still live with your college buddies close to a decade later pretty much says it all. Get your own pad, or share with one cool person, but at the least, hire a house cleaner once a month Normal people beyond the age of 21 shouldn’t live like transient beings at a roach motel.

4. Smokers smell bad. It gets in your hair, on your clothes, and fouls your breath. And what are you doing smoking? Come on, you’re not driving a tractor in Indiana. And since you love to complain about how your looks are leaving you, please realize that the smoking is not doing your complexion any favors.

5. You have a body hair problem. Let’s discuss:

A) First of all, you gotta do something about that stubble on your chin. Please, you can’t claim that you haven’t noticed it. As self-absorbed as you are, you notice microscopic flaws that a trained forensic detective would never detect. There’s waxing, electrolysis, and other ways to get rid of that stuff. If you saved the money you waste on butts and parking tickets, it would pay for itself.

B) Second, the stubble on your legs is like the industrial sandpaper we used to use on the construction crew to remove cement. YES, I do notice it when you try to cuddle just as I’m falling asleep and your barbed wire calves slice open my skin. Maybe it’s not that “I don’t like to cuddle”, but possibly that “I detest pain”?

6. Your friends suck. Granted, they’re your friends and it’s wonderful that you have some, but the drunken bitch you made me sit next to who couldn’t shut up and had nothing positive to say was more than any normal person would or should be subjected to. The other one can’t stand the fact that I blew off her lame advances and hence bad mouths me behind my back all the time. Face it, she flirted with me and never told you; what kind of friend is that?

7. My friends never liked you. I know this is not in itself a justification for dumping someone, but when not ONE of your friends has anything positive to say about your girlfriend, it kind of sends a nice, big, objective, third-party signal. . . .

8. Your almost getting locked up the night I introduced you to my mother did not help your cause. Look, parking tickets aside, you simply have to register your car. And if the three of us are in your car driving to my mom’s birthday dinner, getting us pulled over because a cop notices you haven’t bothered to register your car is just bad potential mother-in-law karma. Believe me, as an only child, and at my advanced age, my mom’s desire for grandchildren has lowered her standards to the point where any breathing, non-crack-whore potential mate will do. This is the first time she has actually questioned my judgment about a girl I am dating.

9. You gotta look sexy, once in a while. Now, I’m not into high maintenance women. But wearing jeans EVERY day just gets a little boring, eventually. I still refuse to believe that every woman doesn’t own at least one skirt. Come on, guys need to see some leg to get the old juices flowing once in a while, even if it is covered in stubble. A dress, skirt, shorts – anything that shows a little skin will do!

10. Your you-know-what is disgusting. Whatever that strange birth control device was that you insisted on using — which caused chronic bleeding and I kept hitting every time we knocked boots — was just not worth it. I was happy to switch to condoms. And please, there’s a reason they refer to trim as “trim”. It really is sexy to trim it. Letting it grow wild, especially with all the congealed blood caught up in it, was too much. That’s why I stopped making house calls.

11. If you have what looks like herpes sores, then get them checked out. Even if you claim they are cold sores. Especially when I ask you to. And stop kissing you. Don’t you even care about your health, and whom you might infect?

12. Constantly denigrating the thing I care most about in life – poetry – is not the best way to kindle my feelings toward you. What is it with you unevolved women, you always think it’s about you? I love poetry, and you don’t, so please don’t take it personally. This is called insecurity. What you are doing is projecting. You project your insecurity by attacking me. This is not good. This is not what loving, mature people do.

13. (A Free, Bonus Reason) Finally, and this is the big one – believe it or not – but you were just TOO into me. You took all of the challenge out if it. Calling me every day, wanting to be with me every night, telling me too soon how great I am. This is not healthy. This is an inversion of the atavistic male/female dynamic. You left nothing left for me to do. No chasing, no winning, no challenge. Please, and take this as sincere advice, you gotta leave something for the guy to do. If the battle is won, all he can do is look for the next battle. . . .

For All the Desperate Nice Guys

After having yet another failure of a relationship before it even begins, I have decided to write a little guide for all you hopeful nice guys who just have no idea how to approach a “cute, funny, and smart” girl. Look, it’s not that we don’t like the initial attention, but please realise that after a week what might seem ‘interested’ to you, comes off as ‘desperate’ to everyone else. It’s creepy, it’s unattractive, and it’s not going to get you laid.

Let’s go from the beginning.

1. The Meet

You meet her at a party, a social gathering, a bar, a park etc and start talking. You find there’s a mutual attraction and you have a fair amount in common, so you get talking about books, movies, jokes or whatever it is you both like, and think you’d like to meet up again. You swap details, maybe a kiss on the cheek, and then return to your currently separate lives. We doing okay here? Good.

2. The Follow-Up

Next off, following up with a text or an email. Leave it till the next night, or the two days after ‘The Meet’, before you follow-up. You want to leave something short that lets her know that someone is thinking about her, that someone is interested in her. This is a warm and fuzzy feeling that most girls like, which is why you want it to be short and sweet and not overdo it. Did she mention she was doing anything the next day? Ask her how it went, or how so-and-so is, something along those lines that isn’t invasive but simply reminds her that you’re interested. You got that? Excellent.

3. The Text Conversation

Now we come to the text conversation. This is her reply to ‘The Follow-Up’, and where you get a chance of playful flirting. Don’t reply the instant you get her text, wait half an hour to an hour (this will also allow you time to think of how to properly reply). Casually drop in that you’d like to maybe see a movie (or the equivalent to whatever your shared interest is) and let her suggest a time. Remember, she has a life of her own which you are only on the fringes of at the moment, so don’t rush it. Let her soak in some well-placed flattery (and for god’s sake it’s called subtlety, don’t just go with ‘I think you’re hot’ or something similarly lame), but just enough so that she’s left wanting more.

4. The Second Follow-Up

This is important. This is the part where you enter either the ‘Casually Confirming’ or ‘Beginning to Seem Desperate’ stage. If you’ve got a possible date on the weekend and she hasn’t replied that week, casually send a text on the Thursday or mid-Friday to confirm. Something like “So how about that…”, something that shows you’re confident and mildly charming. Don’t be insecure with something like “Are we still on for…?” but if you are going that route, change it to “Are you still up for…?” rather than going the ‘we’ angle. You are not part of a ‘we’ yet, that is for you to secretly hope for and her to decide.

5. The Waiting

Look, it is possible that you did have the unfortunate luck to meet her during a very busy time, so if she tells you she’s busy but does still want to meet up, by god you let her tell you when. You do not, under ANY circumstances, begin texting every second day to find out when, when, when? If she’s busy, your texts are not going to help anything, and chances are she’s likely to be more frustrated than usual with a guy chasing her affections. Even if she’s not busy, the ball is in her court so let her have a chance to breathe and go from there.

6. Bonus: Drunken Text Messages

Don’t send them. You are not in any relationship (apart from ‘Possibility’) that is secure enough to allow your hopeless desperation. A few months into steady dating is acceptable for drunken, silly words, two weeks is not.

7. The ‘I don’t think this is what I want’ Rejection

If you have annoyed her enough for her to either call you, text you or email you (chances are she doesn’t really want to see you anymore), saying “I don’t think this is what I want”, then back the hell away. It probably was what she wanted BEFORE you went all creepy and clingy and tried to include her into every aspect of your life. You’ve screwed up, now leave her alone. Don’t suggest still being friends. You’ve creeped her out, now get away, learn from your mistakes and try your luck elsewhere.

Now this isn’t to say you aren’t a nice, funny and caring guy. You probably are, and the girl is probably wishing you weren’t such a near-stalker considering how well you both got along. But really, your desperation is so obvious and so off-putting that unless you find someone equally desperate you’re going to have a hard time finding that “cute, funny and smart” girl you were looking for. Be interested, but not overtly so. Be confident, but understanding. And for the love of god, be just slightly more challenging so the girl can feel like she’s in a relationship with an equal, not with some slobbering (albeit nice) guy who can’t live without her.

This one’s for you. The first and only letter I’ll ever write to you even though you are so not gonna read it.

First of all thanks for making me feel like I was special, now I know I’m not at all. Thanks for smiling every time you saw me across the hallway and came over just to say hi. That was cute.

Thanks also for that time you gave me a little candy you bought with your cigarette. That rocked! Also thanks for that one time I went to your place and we did it all afternoon. That was something else, specially when you didn’t call back the next day. Or the day after that.

That was awesome, you made me feel like a whore. But then again you texted me… man, I felt blessed… you did remember me… Delilah, your friend, the one you couldn’t fuck for an entire year cuz she was playing the hard to catch to you but who really was trying not to fall completely in love with you. Then you ignored me, again. Then you called, to get laid, of course.

Cool, we are fuck buddies, I got it, there’s nothing else besides that. But couldn’t you figure it out?? Couldn’t you?? You do know I’m in love. You do know I’m only pretending to be chill and let things “flow” as you said to me that time, laying in bed, where everything was better just cuz’ of you standing by myside.

You do know It’s fake when I say “let’s just have fun”. Cuz I know that as long as you don’t feel compromise you’ll stay with me. Thanks, voldemort. Really. This makes me feel loved and appreciated.

Oh, and by the way… I hope the other girl, the one I know you don’t talk about cuz you love so much to have the pretty girl I am in your bed like a trophy; I hope she, the other skank, has the chance to infect you with some STD. Cuz God knows I won’t do you again.

The party of the first part (herein referred to as “she”), being of sound mind and pretty good body, agrees to the following with the party of the second part (herein referred to as “him”):

1. FULL DISCLOSURE: At the commencement of said relationship
(colloquially referred to as the “first date”), each party agrees to fully disclose any current girl/boyfriends, dependent children, bizarre religious beliefs, phobias, fears, social diseases, strange political affiliations, or currently active relationships with anyone else that have not yet been terminated.

Further, each party agrees to make known any deep-seated complexes and/or fanatical obsessions with pets, careers, and/or organized sports. Failure to make these disclosures will result in the immediate termination of said relationship before it has a chance to get anywhere.

2. INDEMNIFICATION OF FRIENDS: Both parties agree to hold the person who arranged the liaison (colloquially referred to as the “matchmaker”) blameless in the event that the “fix-up” turns out to be a “real loser” or “psycho bitch”. (For definition of “real loser”, see “John DeLorean My Story”, available at most bookstores, or any picture of Bob Guccione in “Penthouse”. For definition of “psycho bitch,” see Sharon Stone in “Basic Instinct” or Glenn Close in “Fatal Attraction.”)

3. DEFINITION OF RELATIONSHIP: Should said relationship proceed past the first date, both parties mutually agree to use the following terminology in describing their said “dating”: For the first thirty (30) days, both parties consent to say they are “going out”. (This neither implies nor states any guarantee of exclusivity.) Following the first thirty 30) days, both parties may say they are “seeing somebody” and may be referred to by third parties as “an item”. Sixty (60) days following the commencement of the first date, either member may elect to use the terms “girl/boyfriend” or “lover” and their mutual acquaintances may refer to them as “a couple”. Under no circumstances are the phrases “my better half,” “the little woman,” “the old ball and chain,” or “my old man/lady” acceptable. Furthermore, if both members consent, this timetable may be sped up; however, if either party “gets too serious” and disregards this schedule, the other party may dissolve the relationship on the grounds of “moving too fast” and may once again be said to be “on the market.”

4. TERMS OF EXCLUSIVITY: For the first thirty (30) days, both parties agree not to ask questions about the other’s whereabouts on weekends, weeknights, or over long holiday periods. No unreasonable demands or expectations will be made; “rights” or “holds” on the other’s time. Following the first six weeks or forty-five (45) days, if one party continues to be “missing in action” the “wounded party” agrees to “give up”.

5. DATING ETIQUETTE: For the first thirty (30) days, both members of the couple agree to be overly considerate of the other’s work pressures, schedules, and business ambitions. All dates will be made at least twenty-four(24) hours in advance; there will be no “running off in the middle of the night to console an old girl/boyfriend”, and both parties agree to strike the phrase “but he/she needs me” from their vocabularies. Further, during the first six (6) weeks each member of said relationship agrees to attempt one spontaneous home-cooked meal or to arrange the delivery of at least one unexpected bouquet of flowers.
Following the first forty-five (45) days, both parties will return to their normal personalities.

6. TERMS OF PAYMENT: It is agreed that — respective gross income aside “he” will pick up the tab at all dinners, clubs, theaters, and breakfasts until: He considers her suitably impressed, He is broke, or He says, “this is ridiculous, you pay!” Not included in this agreement are meals ordered from the bedroom, which are subject to the availability of discretionary funds on hand at the time.

7. LIVING ARRANGEMENTS (occasionally known as the “Why do I bother to keep my own apartment?” codicil): Should said relationship progress to the point where the couple spends more than four nights a week together, every effort shall be made to split the time between their respective apartments. Further, it is agreed that both sides will attempt to silence the lewd remarks of landlords, or roommates. Both will avoid having their mothers call at 7:30 in the morning. He agrees to “pick up after himself” while in residence at her apartment, including washing his whiskers out of the sink, and assisting with household duties. By the same token, she agrees to respect his right to keep his apartment “a mess”.

8. THE 90-DAY GRACE PERIOD: For the first three months, each member of the phrases couple agrees to hold the other blameless in the euphoric use of like “Let’s move in together,” “Why don’t we start a family?” and – using archaic terminology — “Let’s get married.”

9. THE “L” WORD: For the first sixty (60) days, both parties agree not to use the phrase “I love you.” They may love plants, dogs, cats, cars, concerts, or the way a particular pair of jeans fits, but not each other. Failure by one party to abide by this rule will result in the other party using the “G” word … “Gone.”

10. GROUNDS FOR TERMINATION: Any of the following will be grounds for immediate termination and final dissolution of said relationship:
Infidelity, Running off at any time to console an ex-girl/boyfriend, ending any argument with the sentence “My ex used to do that same ….”