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Advice for a reader: Is he that into me?

Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I recently received an email from a reader asking for advice. She doesn't want me to share her entire email with everyone so I am just going to give you the gist.

She recently met a guy from an online dating site and they have been spending time together. However she is a bit confused due to the fact that he's openly admitted that he is divorced, meets other chicks from the dating site, and is really hung up on woman he met a few months ago who currently has a boyfriend. So she wants to know if he is interested in her or just wants to be friends.

Let me start off by saying that this sounds a lot like how the situation started with me and a guy I like to call Mr. BST. And we all know what happened there. But I don't believe in generalizations because I truly believe that people are who they are. In other words, not everyone is like Mr. BST.

With that said, I don't feel I can give you a clear cut "he's just not that into you" kind of answer here. I don't think anyone can do that. Ultimately he is the only person who knows if he is truly interested in you or not and ultimately you have to decide if you feel he is worth pursuing. The only thing I can really give you are some things to think about based on how I see the whole situation.

If a guy is being open, I mean overly open, about other women he is pursuing that is a huge red flag to. To me, if a guy is interested in you and he knows you are interested in him then what is the point in talking about all of the other women he is going out with? Generally, when you first meet someone I think it's a given that both of you are probably going on dates with other people. So that's pretty much like stating the obvious.

Sure, it's great to be honest (and I am a big fan of being honest) about the fact that you are seeing other people so there is no miscommunication but at the same time you don't need all the details about his interactions with other women. You surely don't need to know how much he really wants to date some other woman.

When you're dating a guy it should be special and you should feel special. And I don't mean in the princess-y special kind of way. I just mean you should feel he genuinely likes you. You should feel important and like he is thinking about you. I don't know about you, but I don't feel very special when a guy is telling me about how much he likes another woman.

And that brings me to a very important point - why do you really want to pursue this guy? Clearly he is hung up on another woman. So hung up that he actually tells you, to your face, that he's still hung up on her. Not to mention the fact that he has also flat out told you that he can't give you what you are looking for. I mean really, does it really matter if he likes you here?

I get the feeling that he probably is too far hung up on this other woman. I also think he could be wishy washy about what he wants. It's probably true that he enjoys your company, but there are too many variables to clearly know why that is. In other words, he could like you or he could just like that you kill the loneliness he feels from wanting this other woman and from being newly divorced (sorry to be harsh there). And, of course, he might not have the balls to tell you that he really doesn't want to date you.

My best advice is to not worry so much about if he is interested in you but really take a step back and figure out how interested you are in him. I think all too often we get too tied up in the whole does he like me sort of thing that we don't look at anything else. You should never determine your interest in a guy by his interest in you.

It's easy to get hung up on a guy you like. Then what happens is you hang on to every little ounce of good that he gives you. And you often discount the bad. You have to look at the whole picture. If he can't give you what you want then why does it even matter if he likes you? Ultimately that is the question you have to ask yourself.

I guess for me it doesn't really matter if he is interested in this kind of situation because through his own admission he can't give you what you want. It's great that you enjoy each other's company but that is not the only important thing in a relationship. And just because he likes spending time with you doesn't mean that he is interested in actually dating you. I like spending lots of time with my guy friends but there is nothing more to it than that.

After all my years of dating, I have learned so many things. Frankly, I don't want to date a guy who is hung up on any woman (other than me of course). I also don't want to be with a guy who clearly isn't ready (or willing to try) to give me what I want. And, I definitely don't want a guy who makes sure that I know that he feels all of this.

Standards are necessary in dating and you have to decide what those standards are.



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Margaret said:

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Well, your reader picked a good gal to go to for dating advice. :-)

I saw plenty of "red flags" given the details that your reader shared with you. The first was that he mentioned he was divorced. There is nothing wrong with this, per se. I've known plenty of normal people who are divorced and move on to new relationships. At least, he was up front about being divorced, but he seems confused anyway.

Not to mention, he was also open about dating other women, which isn't bad either. I assume that's how people use online dating websites, right? You date around, until you meet someone with whom you "click." However, the problem is that he's still hung up on another woman who has since moved on to a new man.

If I met a guy in this particular situation, then I'd head in the other direction. I wouldn't even bother with a friendship. On one hand, I admire his honesty. On the other hand, he sounds like a bit of a douche. I start to see possible reasons he's now divorced (not that all divorce(e)s are douches, but you get the gist).

If a person has to ask too many questions about another person's motives, then it's time to cut ties. Life is too short to waste on trying to figure out someone else. I went through something similar in the recent past, so I'm not saying this as though I'm better than the next person. It's just that we've all had to deal with a similar situation and learn from our mistakes.


Very true. Although I suspect that he's having his cake and eating it in this particular case.

There is so much more that can be said about this particular case, but Jess stated everything so beautifully. :-)

Jessica Downey said:


Thank you so much for the awesome compliments. You are right, there are plenty of red flags. It's perfectly fine to date more than one person from the internet, as long as you aren't seriously dating one of them of course. But it's not necessary to talk about it with every person you meet and definitely a red flag to still be hung up on one. Thanks for all of your added insight!

Margaret said:

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That first "he" should be a "she." Sorry!

Brandi W. said:


Lots of red flag and no green ones except to leave. I think she needs to wake up and realize this guy is a total a-hole and that she deserves better. :-( I think you set it straight to her Jess, nothing more that can be done with this situation other then to walk away and start fresh :-)

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