Am I misinterpreting my friend?

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Dear Guys,

I’ve been interested in a friend of mine, James, off and on over the past couple years. We met in university, and despite what our friends think (and suggest), we don’t have any sort of history. Nothing has ever happened between us, and I’ve never told him that I’ve been interested, namely because when he’s been single I’ve been in a relationship of sorts, and vice versa. As of now, we’re both single, and I’ve been trying to figure out whether or not he’s interested back.

There have been a number of little things that have recently made me wonder about James, such as inviting himself to study with me (within a 9-day period, he visited or studied with me 6 times); recently starting to call me “sweety” and “cutie”, which he’d never done in the previous five years; as well as giving me an overload of compliments on everything from my outfits, to my hair (smell, look, softness), to my photos.

One evening over coffee, we were discussing chivalry and I had said that I appreciate it (or at least aspects of it). He was already a gentleman about opening doors, but since that conversation, he’s opened every door that he possibly could for me, even going as far as to jokingly fight me to get to the door first.

James and I have had an on-going plan to spend a day together in the city, and we’ve always referred it as our “adventure” —adding in anything from lunch or dinner plans, to checking out a museum, to going for drinks and dancing. While we were making plans to attend a festival next month, James suggested we “make our date out of it.” I agreed to it, assuming he was referring to our ‘adventure’ plans, and he responded to say that in spite of the fact that we’ve kept postponing it he was really looking forward to our “overdue city date.” I was a bit taken aback by the fact that he was referring to it as a date, considering we’d never called our plans a date. It was always our adventure.

Am I wrong for having questions about these little things? Does it sound like I’m misinterpreting simple actions of a good friend? Any advice on how I can casually ask him where he stands?


Dear Kate,

Thanks for your question.

We interpret all his actions the same way you do. We definitely think he’s into you, and he’s doing his best to be clear about his intentions, but at the same time trying to be subtle, considering your long past as “just friends.”

Changing the word “adventure” to “date” is a significant and intentional shift in his wording. He’s not sure where you stand on the matter so it’s a very innocuous way of testing the waters. He’s throwing these hints out and seeing if they stick. If you had commented on the fact that he used the word “date” he might have backed off. But the fact that you agreed to it tells us he’ll push this as far as he can.

Our best advice to you is, keep encouraging him by agreeing to whatever he suggests—as long as you’re comfortable with his proposals. After you’ve gone on a few “dates” then it could be time to talk about what’s going on and where the two of you stand. Our gut tells us it will be clear long before you actually have to bring it up. It’s likely you’ll both be sitting in some romantic spot, maybe on a riverbank watching the boats go by, or walking in a park as kids laugh on a nearby playground, and he’ll look you in the eye and the two of you will share a moment. (You may already have, since you wrote to us two weeks ago.)

So enjoy it Kate. The great thing about your situation is that the two of you have been such good friends for so long. It’s not everyday that friends are able to make the leap to romantic partners. If you do manage to make the transition then you already have a comfort level between the two of you that often takes a long time for new partners to reach. That gives you a lot of time to enjoy some of the other “benefits” that come with being in love.  🙂

Good luck, and leave us a follow up comment, or follow up comments. We’d love to hear how things are going.



2 Comments on Am I misinterpreting my friend?

  1. Hey Guys,

    You hit the nail right on the head. Things have been going slowly (the summer was a bit difficult to schedule around), but the ‘friend’ dates have finally evolved into ‘date’ dates, and our share of those little moments have occured more and more frequently. All in all, things are going well.

    Thank you again for your advice! 🙂


  2. We always love to hear great news. Have fun and keep us in the loop.

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