How do you start to a conversation with someone you are trying to pursue over text? 

Sally:

Well first you start off with a simple, “Hey, how’s it going?” to get the ball rolling. Now that we have that covered, the next step is to just start asking some basic questions like how their day went, or about something they are interested in. Start slowly, and then maybe slowly begin to throw in some of the cute emoticons or the classic “hehe.”

Something I have a problem with is responding in a timely manor or just forgetting to respond. You may seem desperate if you respond too quickly, but if you take too long you could come off as uninterested. See how long the guy you are texting takes, and then maybe try to match that.

Beginning of relationships can be awkward and uncomfortable, but you should try to just act normal. Respond in a way you would to your friends at first, and progressively flirt more. Just keep the conversation going by showing interest in what they like, and by asking questions. Show that you have things in common and could even do some of those things together to get in face-to-face time. Conversations will become pretty natural, and won’t be forced or overly thought-out.

But if you’ve been talking for a few weeks and they don’t ask you to hang out, or you don’t talk in person I would suggest moving on. At the end of the day texting is nice when you can’t see you significant other, but it definitely shouldn’t be your only mode of contact. So try to hang out in person, and if it doesn’t work, it just doesn’t work out. There are other people in the world. Good luck!

Xoxo,
Sally

Steve:

The way I see it, a guy can be in three situations with a potential girlfriend: (a) he has never talked to her, (b) he occasionally has a conversation with her around the quad or passing through classes, or (c) he frequently talks with her, shares many classes with her, etc. Each of these stages, (a) through (c) requires different approaches via text or Facebook message when trying to hit on a girl with some social media.

In stage (a), the best way to initiate conversation is with a casual “Hey, what’s up?” without being too creepy about it, trying in a way to introduce yourself. If you can, try and strike up a conversation about the girl’s sports team, classes, performance, or really anything. Just be sure to get talking and turn it so the conversation revolves around HER interests and not yours. Don’t try and be too sleek because you will most likely sound like an over-entitled prick. Once you get past the first contact, the message is your oyster. After a couple days of some meaningless texts, feel free to ask to hangout, see a movie, or whatever else floats your boat.

In stage (b), it makes sense to start off by talking about something you both know about or have maybe briefly talked about at some point. Don’t over-do it in being too personal since you aren’t really very close yet. After a day or two of messaging, supplemented with some face-to-face chats, you can move on at your own pace to fulfill any agenda you may have with the girl. Again, don’t rush it as you will seem like a scumbag looking for something superficial and quick.

Finally, in stage (c) you can essentially talk as if you’re talking to your best bud; just leave out any profanity or slurs you might otherwise use with your boys. Given you essentially have an already healthy relationship, you can take some more risks and be funny. If you think you’re in a friend zone, you might want to move a little faster to the punch line, but otherwise you can move at your own pace. The good thing about being in this position is that even if you fuck up bad, you’re still friends with the girl and can essentially try again in a little while. You definitely have a margin of error to work with.

In general, always supplement empty texts or messages with face-to-face talks on the quad or after school. Don’t be afraid to take some risks, but remember that anything you say over text can be taken many different ways. I would aim to be somewhere in the middle between a George Costanza (Seinfeld) and a Drake Parker (Drake & Josh) on the scale of overly-conservative and overly-flirty. Best of luck in whatever you are trying to do with that girl from across the quad.

Sincerely,
Steve