Ask Him Out Already!! [Ask Tuffy Luv]

Dear Tuffy Luv,

There’s a guy at school with whom I’m smitten, but I’m having a lot of trouble figuring out if the feeling is mutual, or if he just thinks we’re friends. We met at the beginning of the semester through a mutual pal, and really hit it off from the start.

Though our schedules are vastly different, we’ve managed to keep in touch and hang out one-on-one a couple of times: once for a midnight run for milkshakes which turned into a hour long chat in my car, and a second time for lunch (for which he paid) and a movie. We’ve also spent time together on campus a few times, though admittedly not very often–mostly because we’re just never at the same place at the same time. He’s really great to be around: fun, bright, interesting and he’s definitely got a lot of the qualities that I’d look for in a significant other. But, like I said, I’m not sure what’s going on in his head.

At first my girlfriends were pretty convinced that he liked me, but after our movie date (if it even was a date), they aren’t sure. When we parted ways, we both said we had a great time and that we hoped to see each other soon, but I didn’t get a text afterwards. Now, hold the phone–I’m pretty clueless when it comes to dating and guys in general, so I wasn’t sure if that was a big deal. But one of my girlfriends said that if he doesn’t text me within three days, then I should just forget about him.

I didn’t hear from him within her time frame, so I finally broke and sent him a text saying that I hadn’t heard from him, but had an awesome time and wanted him to know. He replied almost immediately and apologized for not texting back, saying he had been super busy (which I knew he was; he’s a full time student with practically a full time job), but he too enjoyed spending that Saturday with me. But now, I haven’t heard from him since.

I know I’m really over-complicating things, but I think it just stems from my insecurities with dating. I’m also a year older than he is, but I can’t really imagine that having anything to do with it, since we had hit it off so well from the start.

Is it worth pining after this boy, or should I take my “three day rule” girlfriend’s advice and just get over it?

Warm wishes,
Friends, Lovers, or Nothing

Dear Friends, Lovers, or Nothing,

I don’t think you should go by your friend’s stupid rule, but I do think you’ve got some thinking to do. I mean, he didn’t ask you out again. And he didn’t let you know he had a good time until after you said something (and then he didn’t make a move). So I kind of think maybe he just wants to be casual friends. But if you’re really pining after him like you say you are, I think you owe to yourself to at least give it one little last shot.

Call the guy and ask him out on a specific date. Invite him to go to dinner or something that you actually would like to do with him. It MUST be specific: an actual flooping time and an actual flooping place.

He will say one of three things:

(1) I’m busy that day, but let’s do it another time! How about Friday?

(2) I’m busy that day. Bye.


(3) Yes!

If it’s (1) or (3), then, YAY!!! You got yourself a date!

If it’s (2), he’s not interested and you can put him out of your mind.

Look, no one’s obligated to like anyone else, and if he just wasn’t feeling it, that’s totally legit. But why not stop fretting and find out for sure? Either you get to go out with him and see if it works, or you find out it’s not going to happen and you can move on with your life and meet someone new. Win-win.

Hearts & Skulls,

Tuffy Luv

Question?!?!?!?!?!? Ask Tuffy Luv. TuffyLuvCC [at] gmail [dot] com



  1. svenerlandson says:

    I gotta agree with you.

    Women are forever saying, "Why doesn't he just grow a pair and ask me out?!!" Yeah, funny. Consider this, most guys have been asking girls out since they were, say, 13. And even the above average guy gets 5-10 no's for every yes. (Don't believe me, just ask any guy to be honest and tell you his no-to-yes ratio, since he was a kid.) And even the most handsome or most successful guys get no's aplenty. Why? Because everyone has different tastes, everyone has a different vibe, and even if a guy/woman is attractive you just may not feel it for that person.

    SOOOO, my point is that most guys have been getting plenty of rejection since they were young. Hence, it really gets old after a while, particularly asking out the really pretty girls (which explains why a lot of pretty gals complain that no one asks em out,, except that overactive guy who has to prove something…the same guy most guys don't even want to hang out with). Rejection sucks for all of us.

    So, ladies, if you're terrified of the possible rejection from asking a guy out, just for a moment consider that guys hate it too, probably even more than you do, because we've been getting rejected for YEARS, because our culture still largely conditions all of us to think that men must be asker-outers! So, if you're interested, cut us some slack and make the first move. Or, AT THE VERY LEAST, smile at us to let us know you're interested. Do you have any idea how many women will completely ignore a guy they're interested in, as if that will somehow make him come after her more? Seriously! Seriously? Just a smile at least lets a guy know that the door is open to approach, which, again, considering the many rejections most guys get preceding every yes, a smile can go a long way.

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