Online Dating Blog

Online dating can introduce some interesting situations and one that I’ve discussed with some women is the issue of becoming interested in a man after you’ve rejected him.

I suppose that this sounds odd to some people, but there are factors with online dating that create this situation. There can be many reasons, but here are a few reasons why a woman may at one point turn a man down but then later find her interest in him growing:

• When women first sign up to an online dating service, they can be bombarded by emails. The number of emails they receive can prevent them from pursuing every guy that contacts them…even if there is some interest. Later, as the number of contacts slow down, they may wish they had responded to him.
• If on the cusp of a serious relationship, a woman could turn a man down to pursue that potentially serious relationship. At some point later, sometimes even months later, she may find herself alone and wishing he would contact her again.
• Sometimes a guy really improves his dating profile and reveals that some of her assumptions/fears may have not been valid.

There are plenty of other reasons a woman might turn a man down at one point and then later find herself interested in him. Here’s another example from a reader:

Here’s a question I want to ask that you have not covered: Do men hold grudges against women they’ve previously asked out online (with which they did not get a yes)? Will they be open to asking that person out again if that person expresses interest again? If yes or no, why is that the case?

I am asking because over a year ago I was asked out by a reasonably cute guy online (we seem to have a lot in common), with which for some reason I did not say yes to. Just recently I came across his profile again, and am now interested but feel that I misled him by not saying yes to a date with him months earlier.

I also hate initiating messages. How do I go about getting him to ask me out again online? And should I even bother?

How Should a Woman Approach Regaining a Man’s Interest?

I don’t think many men hold “grudges” but I do think plenty of men are careful to avoid wasting their time and also avoid being needlessly rejected. When I think about those two areas, I think it changes how a woman would approach talking with that man.

First, she can’t just wait for him to contact her because he’s already tried and most men won’t subject themselves to being repeatedly rejected online by the same woman. Second, I think if the conversation does start again, the woman should be encouraged to suggest a first date. Communicating with him again is not a guarantee that he’s going to think she is interested and therefore ask her out.

Also, as I told the reader in the above example, I think this situation also depends on how the message of rejection was delivered.

The Man was Rejected Through Silence
Once I had a woman contact me several months after I had emailed her (she had never replied). She said she had been very busy at the time that I emailed her but was interested in talking if I still was. I wasn’t bothered by this at all and we did talk, although it didn’t go anywhere. Because of my experience here, I think recovering from silence is pretty easy: write him an email and be honest about what was going on then and why you’d like to start talking now.

Before writing this article I’d never thought about it, but this might be another argument for staying silent in the should-I-openly-reject-him-or-say-nothing debate (which I talked about a few years ago here).

The Man was Rejected More Directly
If you specifically told him at some point that you weren’t interested in dating or talking to him, that does complicate things.

We can’t assume that the man will recognize that you want to date him now (yes, even if you reached out to him). He might just be confused and never ask you out. He might think, “Why does this woman keep emailing me when she said she’s not interested? I don’t want a pen pal!” Because of this, a woman in this situation is going to want to take more initiative than she normally might.

So if you rejected a man directly but are now interested, the following is the approach I would recommend:

1. Send him a short email just to see if he responds. Something like, “Hi XYZ, how have you been doing? I just saw such-and-such and started thinking about you.” You can say whatever you want but I’d suggest making it casual, short and positive. Basically the same advice I give for writing a first email but even shorter.
2. Wait and see if he responds. If he doesn’t, I’d move on.
3. If he does respond, write him again and at this point explain where you were coming from before and ask if he’d be interested in grabbing a coffee. No beating around the bush or emailing for weeks on end: get the show on the road because there’s no guarantee he will. Plus, any delay may just confuse him on why the two of you are communicating.

But I HATE Initiating Communication
The reader above basically wanted the man to gain interest in her again but she didn’t want to do the contacting. That’s a pretty tall order! This is what I told her:

I know you’d like him to ask you out again but I think you need to do the asking. The reason why is because he’s already put you in a category in his mind of “Women Not Interested in Me”. While often guys can be persistent, we also learn to avoid needless rejection. Even if the two of you started getting friendly, he might resist asking you out.

You may hate the idea of starting the conversation or asking him out, but I’d encourage you to give it a try when in this situation. To me, this is the cost of changing your mind. Plus, I’d personally rather know one way or another as quickly as I can. Yeah, you might find yourself being the one rejected this time but that’s better than spending two months emailing each other just to get the same answer!