How long should I wait before I move on?

Dear Guys,

I have a dating question for you. I had been messaging this guy on a dating website for a couple of weeks and it was great because we had a lot to talk about. He kept his last message to me short, asking me to meet up with him for some coffee/tea. The first date went extremely well. He was confident and funny, he was traditional gentleman and we had similar interests. After tea, he invited me to grab some ice cream.

While standing in line (it took over an hour), we began talking about books. I told him about a series of books that I loved (this comes into play later). At the end of the date, we parted ways and the next day I received a text from him saying that he had a really fun time and that we should go get food sometime. I was over the moon, completely smitten, and head-over-heels for this guy. I don’t fall easily for other men, but he really did it for me.

After waiting two days and knowing I wanted to see him on the weekend, I emailed him asking if he wanted to get dinner. He readily agreed and we emailed back and forth on the time/place. He mentioned that he had a small surprise for me. I joked about what it could be, and he joked back.

Sunday came and we met at the restaurant. I was a little nervous because it was much more formal than the previous date. When we sat down, he gave me a wrapped gift. Inside was a book, the newly released one in that series I mentioned earlier. So not only did he think of me and buy me a book, but he also remembered the name of it. The rest of the date went well (or so I hope?). We laughed a lot, I made jokes, we walked around briefly after the dinner and I tried to make an impression on him. Two hours into the date and he offered to drive me home. After dropping me off, I was hoping for some sort of romantic gesture to show me if he was interested or not. Instead, I reached for his car door, awkwardly looked back at him, and he gave me a hug. I exited the car maybe too fast, and ran into my house feeling like an idiot.

I texted him an hour later thanking him for the book, for the laughs, for dinner. He texted back and said he was glad I enjoyed it, and thanked me for hanging out with him. The next morning, I took a photo of the book next to my collection. He replied in a very friendly, non-committal way.

It has now been five days and I haven’t heard a thing from him. I would love, love, love a third date and can’t see any reason why he wouldn’t ask me. (Other than he mentioned that he was going to be busy with a friend’s birthday). I’ve been going crazy trying to decide if I should contact him, or if I should wait for him to do the pursuing. Should I ask him if he’s interested? I don’t want to because I feel like that’s acting a bit desperate. How long is a good amount of time before I just give it up and move on?


Dear Ali,

We can see why you’re a bit confused.

First of all, you’ve got yourself a guy who listens. As you probably know, that fact puts him well ahead of many guys who like to talk about themselves. It also seems like the two of you have a lot in common and enjoy each other’s company.

So what’s the problem? Is there a problem?

It’s unclear to us how he feels about you. He definitely wants you to think he’s a great guy—he gave you the book—but the fact that you were the one who initiated the second date, and the fact that he hasn’t contacted you about a third date, makes us think that he’s not completely sure. There could be several reasons for this.

1. He’s really busy and is waiting until his schedule is free. (To us, this is a lame reason and probably just an excuse. He could at least send you a text or email saying hello. No one’s too busy to do that.)

2. He has another girl he’s dating. (If he’s on a dating website it’s likely he’s got other women interested. Or he’s interested in other women. But that still wouldn’t necessarily deter him from asking you out again.)

3. He’s getting over a serious relationship, and he’s not totally ready. (Not necessarily a bad thing. You’d just have to be patient.)

4. He loves being with you but is not attracted to you physically the way he wants to be. (Every guy is different, so it’s hard for us to say.)

Whatever the reason, one thing’s for sure. He has to be the one to initiate. If you reach out to him, you’ll never know where he really stands, or if he’s into you. You might say, “Well, wouldn’t he say no if he wasn’t interested?”

Remember this: Guys love an easy road. But they don’t necessarily love what’s at the end of that easy road.

One simple way to determine if he’s into you is observe how hard he’s working. We’re not saying you should make things hard for him. Sometimes women play that game and eventually it turns off the guy. We’re just saying that the ball is in his court and he has to be the one to pursue you. He has to be the one working and planning.

How long should you wait before you move on? Up to you. If it was us, we’d say there’s no rush. Wait for as long as you want. But while you’re waiting, date other people, put yourself out there. He seems like a nice guy, but if he’s not going to step up to the plate, then there are other nice guys that might.

Good luck,


ps. Do not ask him how he feels right now. It’s way too soon for that. 

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