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Faking, Other Women, and the Top 50 Proposal Jokes

I’ve known a guy for about eight years now, and during that time I’ve pretty much always had feelings for him. We’re now good friends, but it’s hard because he has a girlfriend. However, he recently told me that he liked me and drunkenly tried to have sex with me. I would have gone for it, except I don’t want to be the other woman.

So, I have a couple choices. I could not go for it and maybe never be with him, or I could tell him to break up with his girlfriend to be with me (I’m sure the actual situation wouldn’t be this simple, but that would be the goal). The problem is, I don’t know if we would work well together. I know that we get along really well, and the one time we did have an intense makeout session, it was the best I’ve had, but I don’t know if we’d be good in a relationship. I don’t have that much relationship experience and tend to shy away from commitment, but I really like this guy. But I don’t want to be the cause of his breakup and then our relationship be a disappointment to both of us. It’s hard to weigh the pros and cons, because a lot of it would depend on how great it would be to be together — something I’ve been avoiding, since it hasn’t really been possible.

It always seems hard to weigh the pros and cons when the cons clearly, overwhelmingly outweigh the pros, yet the pros are related to complete fantasy and an intense makeout session. But take a step back from what you’ve written and read it as if a friend had sent it to you. What advice would you give her? What evidence would you have to endorse this as a good move for her?

My guess is that you wouldn’t have much evidence at all, and you’d tell her to forget about him and move on. I mean, what are we talking about, here? An eight-year, pretty good friendship that culminated in him telling you how much he liked you right before trying to make sweet, drunken, semi-erect love to you? You kids and your romance! Do you live in a town with one boy? If so, maybe he has a cousin one town over?

You’re better than this. Here’s what I want you to do. Wake up tomorrow and tell yourself it is the first day of the rest of your life. Put on some athletic shoes. Go for a brisk walk. Breathe in the morning air. Listen to nature. Come home and read the news of the world. Think about it. Make a nice, healthy breakfast. Take a hot bath. Go to the mirror. Look at yourself for five minutes as if you were someone else. Write down the fake conversation you have with your mirror other. Call your grandmother. If you don’t have a grandmother, replace with any older, wiser woman. Tell her about the fake conversation as if it were real. Listen to what she says. Get dressed. Go about your day. Eat lunch and dinner with someone interesting. Come home. Go to bed early. Get a good night’s sleep. Wake up. Repeat, except this time, skip the fake conversation, tell your grandmother about the real conversations during lunch and dinner. Listen to what she says.

Do this until it becomes second nature. Then, wake up. Tell yourself it’s the first day of the rest of your life. Walk. Breathe. Listen. Read. Think. Eat. Bath. Mirror. Back to fake conversation. Write it down. Compare it to the first one.

After that, I don’t know, I’m just trying to give you something else to do for the next eight years other than worry about this turkey.

So, I’m in a long distance relationship with this lovely guy for just over a year. He is in the UK, I’m in the US, I’m planning on moving over there soon, and I’ve been going back and forth a lot. (I’m not just moving because of him, I want to attend grad school over there and hopefully permanently relocate.) Anyway, we’re planning on living together this coming year, which I’m excited for! The thing is, recently he’s been joking around about proposing and marrying me.

He visited me in the US and would say things like “I was thinking about asking your dad for permission” and “Should I propose at dinner tonight or after?” and my response would be joking back like “Shouldn’t you ask me for permission first?” So I thought I was being non-threatening. This behavior confused me, because he always said he wanted to live with someone before getting married, and I’m not sure where he’s coming from, so naturally I asked him. When I asked him he got defensive, said he didn’t want to talk about it, said it was far from his mind, which is why he could joke about it and also repeated that he would need to live with someone first, which is completely understandable. But, I’m not wanting to get married yet, it’s not like I’m asking him to propose! And his reaction was quite strange to me (he’s usually really easy to talk to about serious things), and I didn’t quite believe him. I think I brought it up bluntly (because I’m direct!) and it scared him. So, finally, my questions are 1) Why do you think he joked (and continues to joke) about proposing? 2) Why did he react so defensively? 3) How can I talk about it with him without the defensive reaction?

1) He’s anxious about the reality of you every day. Not in a bad way, necessarily. He’s making a joke about marriage to see if you’ll say “OOH YES FINALLY MY DAD AND I HAVE BEEN WAITING FOR YOU TO ASK THANK YOU,” so he can validate his fears that his bachelor life is officially over.

2) He really isn’t opposed to his bachelor life being officially over but is still anxious. It’s a big deal. He feels vulnerable. What if it doesn’t work out? What if you don’t like him every day in real life? Oh haha he didn’t care anyway haha. You thought he was serious? Oh man haha. He was definitely not serious. Phew. Well, dodged that bullet. Anyway! Back to ye good olde bachelor life days of glory! *sobs*

3) Make jokes about the above. Tell him you’re anxious, too, and that it’s okay. That no matter what happens, you’re making the move for yourself, not him. It’ll be fun! [Sidebar: watch Beginners with him. So sad, so great!]

Greetings, A Dude. Here’s the situation: I have decided to jump into the world of internet dating! Whee! The problem is that I’m what you’d probably call a late bloomer.  I’m thirty-three, I’ve had exactly two “relationships,” the longest of which lasted three months, so will it totally shock you to discover that I’ve never actually had sex?  What can I say, it just wasn’t a big priority in college (when it’s supposed to be?), and I’m (obviously) not a big dater, and for a while I had a problem that made trying to have sex painful, and blah, blah, here I am, an adult woman who has never experienced something that’s a pretty significant part of life.  And I’d like to.  Y’know, with someone nice.

So … my question is when, exactly, does a girl drop this bomb on someone?  I mean, I’m not planning on leading with this information. (“Hi, great to meet you! You look almost just like your picture! I’ve never had sex! You want to order drinks now?”) But — maybe because I watch way too many Sex and the City reruns — I feel like maybe sex is on the table as an option before sharing deep dark secrets is? And I don’t want to get to that awkward point — it’s happened before — when we’re making out, and it’s great, and then it becomes obvious it’s going to go further, and then I have to decide between faking my way through something or initiating an honest but awkward (and ill-timed) conversation. (I have been in this situation, albeit only a couple times, and I chose to go the faking-it route — I know, I know — and it culminated in a) lots of physical discomfort and me finally saying, “Okay, stop,” and b) me still having to have the awkward-but-honest conversation.)

Also, is this totally going to freak a dude out?  I mean, it’s one thing if I held off having sex because of religious beliefs, or I had some other really serious reason, but basically, for me, it just comes down to, “Eh, I just haven’t done it yet.”

Greetings! I am shocked by nothing! Whee! Stop faking it! I think you should always err on the side of honesty, especially when dating online, where it’s much easier to fudge the truth in order to improve your search results. If you make it a policy to be as truthful as possible in building your profile and reading your suitors’ profiles, then you’ll end up with a better pool of candidates, ones who are already attracted to the real you and appreciate your honesty. And when you do inevitably get to the brink again, and that honesty policy is in place, then it’s less likely that what you say will freak that dude out. Your relative inexperience is not actually that freak out-worthy, anyway, but it’s still a delicate balance if you’re trying to keep the chemicals flowing for both of you. It may end up in a few more awkward conversations, but it will also likely end up that, when it isn’t awkward, you’ll recognize it pretty quickly, and maybe that’s when you’ll know it’s the right time. Or you could just hire a man hooker aaaaaaaaaand I’m joking. Good luck!

Dude. Is there a good (i.e. less awful) way to ask someone whether you made out with them when you were drunk?

Are there any not-good ways?

Previously: Treating and Sitting and Smoking and Talking.

A Dude is one of several rotating dudes who know everything. Do you have any questions for A Dude? (300 word max, please.)

Photo by Felix Mizioznikov, via Shutterstock

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