How Do You Know If You’re Ready to Propose?

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Q: My senior prom is in a couple of weeks and I found out that prom date does not want to get with me. How should I act towards her that night?.. I was originally going to try to get with her. Now that I know this, Should I still try?

A: What you do is act normal; you act is if you never received that shitty tip-off in the first place my friend. You have no idea how solid or valid the information you received is, and even if it were initially true, who’s to say you won’t change her mind by showing her a bitching fucking evening?

That said, a prom date– or any date for that matter– should never be considered as a Get Laid Free card.

That’s not a fair thing to assume or expect from another person based solely on a single-night commitment, regardless of the circumstance– so keep that in mind.

Maybe she doesn’t have any interest in having sex with you, maybe she’s nervous, or maybe she just has no fucking clue either way.

But don’t let that affect the mindset. You keep walking into what should be a night memorable enough to regale to your children.

Of course using your discretion to skip over certain details.

Be a gentleman, tailor your pant hems, and bring a condom just in case.

Nobody wants to be related to, “the chick who got knocked up at prom”, amirite??

Q: There is this woman who a friend of mine is kind of seeing. They aren’t exclusive or anything. He still talks to other women. The woman wants me though. How can I handle this situation without losing the friend if something did come about from this?

A: “The woman” in question may want you, but the fact of the matter is that until she stops wanting your friend at the same time, you have to hold off. Period.

Unless you’re secretly hoping for some strange threesome action or a friendship-terminating blowout, waiting it out is your only option. Maybe you’re into crossing swords; I don’t know. Nor do I care.

But what I do know is that sneaking around with a friend’s partner, no matter how “not exclusive” they are, is the best way to land yourself with a puffy black eye and painful set of blue balls.

The woman has got to be the one to select you or your friend as the guy she wants to bone, because in the long run she is most definitely not worth the loss of a friendship.

Q: My ex-girlfriend and I broke up about a year ago. Since then we went through a stage where we didn’t speak at all and now we are pretty good friends. We still flirt on occasion and help each other out with everything. She has a boyfriend now, but I still have strong feelings for her. I leave for deployment in a few days and I will be gone for seven months. I told her how I felt about her and I asked her if there was ever a chance that we would get back together. She sort of dodged the question and since then hasn’t returned my texts or phone calls. Do I take this as her version of a “no” or do I assume she is afraid of her feelings for me too because of the fact that she is in a relationship now?

Should I just move on all together and forget about her or should I wait the seven months and try again in person? I once thought I was going to marry this girl, and a part of me still believes that I will.

A: Soldierbreau, it genuinely disheartens me to have to strike you with such painful honesty before you jet off to serve our country, but I suggest stocking up on some pinups for the trip. Because your ex is no longer interested, and certainly is not waiting around considering a change of heart.

She has moved on, and if she had any questions about that whatsoever, she would have given a more indicative response when asked rather than dodging the question.

On the bright side, having the ability to maintain a friendship is huge, even if its not everything that you want. Take that at face value and try to avoid writing any nostalgic love notes while deployed.

Q: So I’ve had this problem so many times in my life. I start seeing a girl for a month or 2 of casual dating. When she starts to meet my friends or we run into an acquaintance they always feel compelled to ask, “So is this your girlfriend?” or “Are you two dating?”

It’s backfired on me before where I thought I was dating a girl but maybe we were just “talking” or “seeing each other” and I jump the gun and may have ruined a great potential relationship.

So what is the best answer to give to someone who asks a premature “is this your girlfriend” question to someone you are casually dating and would like to be your girlfriend in the future?

A: First of all – why are you friends such douchebags?

They’re clearly out to sabotage you and I think you should get a new batch.

If you disagree or are unable to do so, I at least think you should train them in the art of discretion. ALWAYS give them a heads up prior to questionable encounters when possible and tell them to PLAY IT COOL, MAN.

As far as random run-ins go, I find it odd that so many people show such vested interests in your personal life.

They kind of seem like douchebags too, but since they’re less predictable lets strategize how best to approach it.

When asked up front about the status of you and another woman, you need to respond with confidence– never seem uncertain as that will make said girl question it herself.

Keep it short, keep it sweet, keep it vague; “Yeah, she’s tolerating me for the time being”, or, “Depends how long I can keep her interested”.

Something funny, indirect, and hopefully substantial enough for that person to shut the fuck up.

She’ll be impressed with your poise as well, and will have a boosted sense of confidence as a result of it.

Be ready for the next encounter. Don’t let some asshole on the street ruin a good thing for you.

Good luck.

Q: I’ve been dating my girlfriend for a little over four years. I’m at the age where friends are getting engaged, people are looking for more serious relationships if they’re not in them, etc…

I guess I’m not sure if I’m ready to take the plunge and seems like a lot of people do it just because it seems like the right time.

Not to be super lame here but how do you know if you should pop the question? I love my girlfriend but I have no clue if now is the time/person.

A: In asking said question about popping the question, you have, in fact, answered your own question. Does that answer your question?

If you aren’t sure, you aren’t sure. So play it out. Don’t let developing social norms dictate any of your major life decisions– particularly ones that are becoming increasingly antiquated choices. Like marriage.

Not everyone does it anymore, nor should they feel weird about the decision to forego it. So take that into consideration when putting arbitrary pressure on yourself.

You don’t owe Facebook, or your girlfriends BFF’s, or even your grandma, anything at all. This is your life.

Our generation is slated to make it to the age of 105– do you REALLY want to look back at your 75 years on earth with the same person as a choice you made based on…what was expected of you at the time?

I didn’t fucking think so. Take a step back for a bigger picture perspective here. If it’s right, its right.

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