Finally, at long last…we’ve got our first Ask Jesscolumn up! Keep sending in your questions to , with “Ask Jess” in the subject line, and I’ll get to as many of them as possible.

Enjoy!

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Dear Jess,

I’ve been hanging out with this guy – a mutual friend introduced us because we work in the same industry and I was looking to switch jobs, so she thought that he might be able to help me out. We immediately hit it off, and after a few coffees and happy hours, we started making out on a regular basis. He’s really great and has never seemed like a game player. I have high hopes for where this could go.

BUT, something weird is happening. We hung out four times last week, which is way more often than before. And then for three days, he didn’t respond to any of my emails or texts! Nothing! He finally replied to one of my emails a few minutes ago with a short, cute joke, but he didn’t ask me to hang out…

How should I respond? Can I be the one to suggest that we hang out? You know, female empowerment and all that? He’s being strange, but I have trouble believing that he’s suddenly blowing me off or isn’t into me anymore. We were having so much fun!

Love,
Trying Really Hard Not To Be That Stalker Girl

Dear TRHNTBTSG,

You can definitely write him back, but *do not* ask him to hang out right now. Instead, say something casual and fun – something that he can respond back to without having to say YES, let’s hang out, or NO, I’m blowing you off.

Here is why it’s smarter to be laid-back and undemanding, for the time being. I see this shift happen often with guys, and it always happens right after you start hanging out with him on a more regular basis. Right when you begin to feel like your relationship is reaching the next level of regularity and intimacy and involvement. At this point, if there’s any tiny piece of him that’s not 100% sure that he’s looking for something serious, then THIS is when he’ll have a little freakout and pull away.

The freakout is probably not about whether he’s into you. It’s more about him realizing that he’s getting closer to relationship territory, and needing to take some time to make sure he wants that and is going to head in that direction willingly. He may not even be completely conscious of his fears and the dumb decisions that he’s making because of them – more likely, he just begins feeling like the walls are closing in on him whenever your name pops up in his inbox.

His issue, not yours. Except that when you like a guy, then it suddenly becomes your issue, doesn’t it?

The worst way that I see girls – and myself, of course! – handle this phase is to push guys into making decisions or getting over their freakouts earlier than they’re ready to. We’re more likely to want to “talk through” the rough patch, as opposed to avoiding each other completely while we figure out our feelings. But have you ever experienced claustrophobia? Having someone constantly ask you to measure the floors and walls around you and explain how you’re feeling is NOT helpful. Given an exit door, YOU WILL RUN.

If he’s feeling cornered (and again, that’s his own problem – I’m not saying that it’s because YOU’VE been cornering him!), then pushing him to hang out or give you answers or explain himself, even if you think that you sound light and casual about it, will inevitably lead him to call the whole thing off. That’s exactly what guys expect us girls to do, and then we panic and go ahead and do it, and then they justify to themselves why they got nervous in the first place (“Dude, I told you that girl would turn out to be craaaaaazy! Glad I dodged that bullet.”).

The best way to get through this freakout stage, in my humble opinion, is to remain in contact with him without pushing the hanging out or hooking up aspect of your relationship. This will give him a chance to relax and work through his issues without forgetting how awesome you are, and will make you look a lot more sane and chill than the high maintenance girls who he may have dealt with in the past. The fact is, and never forget this – he knows where to reach you, once he feels ready and excited to hang out again. Which could be tomorrow! Who knows?

So in the meantime, do other stuff! Focus on work and friends and other guys who you may be talking to (you don’t owe him anything!), and respond to correspondence from him in a casual, fun, no-pressure, “You mean something’s wrong? I’ve been so busy the past few days, I didn’t even notice that you hadn’t written me back!” way. It will be easier for him to communicate with you when he doesn’t feel immense pressure and expectation attached to every Facebook wall post. And more importantly, you’ll start to actually BE and FEEL like that calm, collected and easygoing girl – sane thoughts will follow sane actions.

But just as you don’t need to push the hangout right now, you also don’t need to totally ignore him and write him off ala He’s Just Not That Into You. You can’t know what he’s thinking until he tells you, so stop trying to figure it out. Just treat him in the same wonderful, confident, great way that you treat everyone else, and if he’s eventually able to wrap his head around his freakout, then he’ll be back and in action and it’ll seem like nothing happened. Don’t automatically blow three contact-less days way out of proportion.

(For the record, I don’t see this as you having to play games. It’s just you, living your life, reigning in the intensity a bit and letting him come to the realization that his life is more fun with you in it. And if that doesn’t happen, then at least you’ve started to emotionally detach and will have an easier time moving on.)

WTF?! BOTTOM LINE: Stay in touch, but don’t push him for answers or explanations right now. Guys will usually err on the side of blowing you off, if they start to feel pressured. And anyway, you’re way too awesome to act needy and desperate with some guy who may not even deserve you, right?

P.S. Do not, under any circumstances, refer to him as “Stranger” in any interaction. Believe it or not, boys see right through that stuff! I know you may think it sounds cute and light and funny, but nope. It sounds passive aggressive. “Hey stranger!” = “Don’t think I haven’t noticed that you’ve been blowing off my texts and emails, even though I’m going to pretend to be cool and casual about it. But seriously, where the hell have you been?! Explain yourself! Grovel for my forgiveness! Tell me that your phone and computer both got run over by cars!” Just don’t do it.