How do I know he’s interested?

Hello Guys,

First of all, I apologize because I have a LOT of questions! The reason being, I have never dated anyone before, never been remotely interested in anyone before, and I am in my late 20s. I thought for a while I was asexual and I was perfectly fine with that.

But now, I met a friend of a friend, and I am basically shocked to realize I’ve fallen really hard for him. Several problems with this:

1. I’m currently attending school a two hour flight away. I still visit my hometown (where he lives) during my breaks, but that’s becoming less frequent as I’m getting busier with my schoolwork.

2. Like I mentioned before, I have ZERO experience, in ANYTHING. This includes the dating game, flirting/trying to convey interest, and sex. He is the complete opposite, and is very experienced.

3. I heard from my mutual friend that he recently went through some rough times with a Friends with Benefits, who he may have had actual feelings for. (Obviously things didn’t work out.)

My questions:

1. So I don’t even know how to properly flirt with a guy in person, let alone long distance. On top of that, I have no idea how to read whether he’s interested or not. We’ve always chatted online, but over the past few weeks we now chat every night. Am I reading too much into this change, getting hopeful that this might mean something? We have a LOT in common, a lot of similar interests, etc so we never run out of things to talk about.

2. How can I express to him that I’m interested in a relationship, even if it is long distance? How do I even bring that up without making it awkward? Would it be too weird for me to ask about it since most of our interaction so far has been online? (Though whenever I’m home, we go hiking or play board games with our mutual friends so I have spent face-to-face time with him) Is it not even the right time, since he went through that whole drama with his FWB? That happened at least two months ago, is that usually long enough for most guys to get over a bad breakup/relationship or should I back off?

3. Would it be really off-putting to him to go out with someone like me, who is so inexperienced in everything? Is that something most guys might shy away from?

Again, sorry for this ginormous essay. Thanks for all you guys do, this website is really great and I’ll probably be referencing it quite a lot from here on out!



Dear Anon,

Thanks for your kind words.

We can reassure you that your inexperience will have nothing to do with whether or not he’s interested. It will simply come down to whether or not he’s attracted to you and sees you as someone he might date or not. And we’ll let you in on a little secret: Guys feel good when they are a bit more experienced. When the roles are reversed—the woman being more experienced—it can sometimes be tough on the guy, especially when it comes to sex. (It’s that ego thing.)

It sounds as if you have a nice rapport, and you’re becoming closer friends. Has he ever hinted that he might want more with you? In person? On the phone? Has he ever joked about the two of you as a couple? Or made sexually suggestive remarks, all in the guise of fun? Has he flirted? (Usually involves sex, or something like that.) Or said something like, “Oh, your boyfriend probably would….” Does he ever tease you? Or tried to tease information out of you? Basically, has he ever tried to fish around and find out more about your personal life? These would all be signs that he might want more with you.

On the flip side. You could also try doing the same with him. 

Ideally Anon, you’ll let him take the lead here. If you tell him how you feel without knowing how he feels, and he doesn’t reciprocate, it will definitely get awkward and it could change your friendship. (Is that a risk you’re willing to take at this juncture?) However, there’s another option. Would it be possible to invite him to visit without making it too heavy? Maybe the city your school is in is a lot of fun and you could focus on that aspect of a visit? Say something like, “If you ever need a break, you should come visit, there’s lots of fun stuff to do here.” This is just a thought. Obviously, you know the situation better than us, and whether or not he’d be open to an invitation.

This is one of those situations where this isn’t a right way to do things. If he’s into you, it will work itself out. If he’s not, it won’t.

Keep us posted. And let us know if you have any follow-up questions. Please leave in the comments’ section below.



ps. We hope you’ll share our site with your friends. Thanks!

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