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. 

11 Comments on How long should I wait before I move on?

  1. Charlie Tango // May 30, 2017 at 3:19 pm //

    A man I’m talking to and we have a lot of the same beliefs and great conversation is talking to another girl who doesn’t have him same beliefs. But, he says I can still message. Do I patiently keep that door open while I date other men? He’s a one woman at a time man and won’t entertain any ideas of us while he’s talking to her.

  2. @Charlie……So why wouldn’t you keep the door open? Are you worried that you’ll be kind of emotionally stuck and not available to other men while you’re waiting for him? If you think you can date other men and actually be open to them AND still keep the door open for this other guy, then by all means stay the course. What do you think? Note: Remember, he has to feel the same way you do. And if he thought you were “the one for him” he’d likely stop talking to this other girl. (Just some info for you to percolate on.)

  3. Charlie Tango // May 31, 2017 at 12:08 pm //

    I’m afraid of keeping the door open and being let down. I can’t tell what his attraction of me is because he want entertain any ideas while talking to her. He said he’s not rushing into a relationship and taking it slow. I want to keep the door open.

  4. @Charlie……Like we said, keep the door open if you need to. But we’ll repeat…….If he was way into you, he’d stop talking to this other woman and start talking to you. But instead, he’s keeping his options open. He’s seeing if it will work out with her and if not, then maybe you. Do you get the sense that you’re his 2nd option? What do you think?

  5. Charlie // May 31, 2017 at 4:39 pm //

    I don’t know, I can’t get any deeper reactions out of him other than him saying I’m a lovely woman. Any suggestions?

  6. @Charlie….How did you meet? How are you communicating with him?

  7. Charlie // May 31, 2017 at 8:33 pm //

    We connected by way of a dating site and we’re communicating through messaging.

  8. Went on a date with this guy who was amazing, we had a lot of fun, great conversation laughs, we have a lot of similar interests. When he dropped me off he just hugged me and I had asked if he would be interested in going out again, all he said was “I’ll call”.
    Does that mean he’s interested in going out again and should I be concerned he didn’t kiss me?

  9. @Julia…..There could be a number of reasons he didn’t kiss you. 1. He was nervous. 2. He didn’t want you to think he was like that. 3. He didn’t see the need to rush things. etc. That said, let him initiate from now on. The fact that it was you, not him, who asked about a second date is slightly concerning, but it’s too soon to jump to any conclusions. See what happens this next week and then check in with us later in the week. Sound like a plan? Take care.

  10. Hello,

    Me and my friend are from different cultures and living in different countries. We both liked each other a lot and I had the idea that we could live together in another different country and be in a relationship. Anyway because of his and religion (Islam) I thought he should ask his mum (his dad has passed away) what she thought about this and he said he would. Well it’s been a month since I asked him to ask her and he still hasn’t asked. He said he needs more time. Do you think he was ever going to ask? There is also the slight problem that he is a muslim and I wouldn’t become one. (Not allowed in Islam). Thanks for the help

  11. @Sophie…..Before we respond we had a few questions for you. 1. How did you meet this guy? 2. What countries do you live in? 3. How long have you known him? 4. What country do you plan on moving to? 5. How old are you both?

Leave a comment

Your email address will not be published.

Maximum comment length is 1500 characters.