One of my friends went through a rough break-up last year (they were in different places in their lives, she didn’t pay attention to him, etc) and he’s been pessimistic about dating since. It’s been about a year and a half I’ve been trying to set him up occasionally, encourage him to get out there and all since he says he wants a relationship. But he’s dead-set against online dating, and he says he doesn’t know how to ask a girl out. I have zero casual dating experience (all my SOs were friends first.) So here are some questions he asked me that I don’t think there is a ‘right’ answer to but he seems to think there’s some average answer:

1) How long does a guy typically wait before asking out a girl (assuming they just met)?

2) How long does it take for a girl to decide that a guy she meets is ‘friend-zoned’?

3) Any other personal advice about dating you could give.

My boyfriend and I got into a really heated fight last night, and I’m wondering if most people have guidelines for when a fight becomes more than a fight and becomes grounds for dismissal? Have you ever broken up with someone over one fight, or how much does it take before you’re ready to end it over something like that?

Does anyone have any horror stories from online dating? I’ve had online dates be pretty boring, but thankfully nothing was ever too bad. There must be some interesting stories out there from bad online dates, let’s hear them! Did the guy look totally different from his photo? Did the girl have an incredibly annoying voice that you just couldn’t stand?

In the constantly expanding digital age, people communicate via technology far more these days. One things I’ve noticed is that if I’m talking to a girl, regardless of whether there’s anything actually going on, they sometimes become annoyed or even down right angry if I don’t end my messages with an X.

When I have been talking to a girl whom I’m interested in, I’ve been told that not ending my messages with X, is akin to saying I don’t like them, which obviously isn’t true. I just grew up with a phone without a 9 key, and as a result, never got into the habit of putting kisses on the end of a message, now that I’m grown up, it just feels awkward to do.

But it did make me wonder, does putting kisses on the end of a message really change how people view it and is it a habit I should get into?

With your significant other? Do you expect that they’ll clear all plans with you before making them? My fiance’s generally pretty good about making sure that I come first, but I was pretty frustrated this week that he made a bunch of plans that didn’t involve me without running it by me first. We both have pretty odd schedules with work and school, so I like to prioritize our time together. Do you expect to see your boyfriend or girlfriend every night of the week? Every other night? Once a week? How do you communicate your schedules and what are your expectations?

How long should you date someone before having a conversation with them about where the relationship is going?

If you’re a guy, how do you view those conversations?  Have you ever brought it up yourself?  Because it seems like it is always the girl who ends up initiating the topic.

What are the pitfalls one should watch out for?  I’m asking generally, but also, for some context, I am thinking about having this conversation with someone I’ve been seeing for a few months now.  It’s been casual, but I think I’d like to clarify, at some point in the near future, what we’re both looking for, i.e. do we continue with the casual dating? should we agree not to sleep with other people? if things keep going well, do we each see ourselves in a more serious relationship at some point? 

For about two years, I worked in an office with this guy “Josh.” We ended up getting assigned to a few projects together, and whenever we were working together, we always got along fabulously. So I admit, I started developing pretty strong feelings for him. I never did anything about it, since we worked together, but when I decided to take a new job, I figured maybe something could happen. I never actually knew if he felt the same way about me, but any time we were together, we were always flirting.

About a week before my last day, a bunch of my coworkers and I went to happy hour. Josh was there, too. Pretty much the whole time that we were there, he and I had our own conversation going. I’m pretty sure everyone noticed the rapport we had, too. And I’m sure it didn’t help when Josh turned to another coworker near the end of the night and said, “Oh I god, I’m gonna miss [my name] so much. Seriously, I just love her. Isn’t she just the most amazing girl?”

Of course, I was totally excited to hear that, and throughout my last week of work, I was expecting him to ask me out. Well, he never did. And now, it’s been about three weeks since I left the job, and I haven’t heard a thing from him. I’ve texted and emailed him a few times just to say hi, and he always responds, and it’s always our usual flirty banter. But, that’s it. He’s never initiated the text or email himself.

So am I over-thinking things? Was he just being flattering to me? Did he really “love” me? I think about that night and what he said all the time, and I just don’t understand what he could have meant by his words. What should I do? I feel like maybe I should call or at least text him and ask him about what he said. But then I’m not sure if I’d be too forward and aggressive. If he really liked me, he would have asked me out, right? Maybe I just need closure, because I keep hoping that he actually has feelings for me, but maybe he doesn’t after all.

Do you have any particular criteria for what constitutes a great first date for you? For example, do you look for hours of great conversation? A feeling of butterflies in your stomach? A great kiss? What helps tip the scales towards a second date?

I’ve got to say that being dumped via text message was pretty bad, but the worst was when this guy posted a very passive-agressive blog spelling out things he didn’t like about me. He didn’t mention me by name, but it was pretty obvious by the content that he was dissing me. And it wasn’t even anything major; it was all really stupid, petty stuff. For instance, I was excited about getting a new iPod for Christmas, and he went on about how inferior iPods are to old-school record players and how lame it was to be excited over something that would lead to the downfall of the music listening experience as we know it. (Then again, this is the same guy that said he thought the downfall of humanity came with the invention of the toothbrush, so take anything he says with a shaker of salt.)

How about you guys? Any heartbreak horror stories you’d like to share?