Well, as a nice change of pace from all the Emails from disenchanted women telling me that I’m an asshole, an email came in the other day from a young man in a sensitive situation. Let’s call him…Fred!

Here are the key points from Fred’s email:

• Fred is no stranger to the art of getting girls.
• Fred just broke up with his girlfriend of six years.
• One of Fred’s new ex’s friends has entered his life and offered her support.
• Fred is balling, she’s not, but when they hang out she won’t let Fred pay for anything.
• Fred finds this girl unreadable, and can’t figure out for the life of him if she’s interested.

Well Fred, one huge thing you need to take into account is the fact that you were tied up with the same girl for six years. It doesn’t matter if you were pulling 12 girls a week prior to that relationship, six years will definitely put some rust on your gears. After being with one person for that long, things become awfully familiar. The things your girlfriend of 4, 5, or 6 years does to show her interest is a world apart from a girl that you’ve been seeing for just a couple weeks. I think you know that, but you might need someone to remind you.

The fact that she won’t let you pay for anything could be construed as a sign of disinterest, if it weren’t for the fact that you mentioned she constantly shows an interest in hanging out with you (more than you reciprocate). In this case, I’d call it GOLDEN. If for no other reason than it’s so difficult to find a girl in this day and age that has a little bit of integrity and won’t easily allow a guy to pay for her shit. It could very well be that she is aware of your income bracket (if she couldn’t tell by your car, she heard from your ex), and she is simply too humble to let you pay, or she is intimidated and afraid to look broke. You have to remember that a lot of girls have no problem letting guys pay for stuff who they have absolutely no intention of having any sort of relationship with.

Above all else, the biggest indication of the fact that this girl is into you is the fact that she had the nerve to waltz into your life so soon after you ended things with her friend. Generally, this is frowned upon in the female community. Even if her friend (your ex) gave her expressed consent for her to hang out with you, she wouldn’t mean it. She would just be holding onto her pride and attempting to “get over you”. This new girl would not make such a bold move unless she thought it would be worth it, and it doesn’t make a lot of sense to jeopardize one friendship simply for the sake of another (much newer) one.

You asked for my opinion, so this is what you get! If I was to wager on this situation, I would most definitely put my money on “she’s into you”.  I have a feeling that the fact that you just got out of that longterm relationship has rendered you sort of stuck in that awkward place, where you feel like you have to relearn how to be with someone new. Honestly, she’s probably wondering why you haven’t made a move yet. And I bet the old Fred most definitely already would have! From the sound of things, the ball is still in your court and she isn’t losing interest. In fact, you may have inadvertently dug the hook in even deeper by making her doubt that you’re interested in her.

You mentioned that you’re not even sure you want to get into another relationship, which is totally understandable. It sounds to me like you definitely have the option, so the question isn’t so much “is she into me?” but rather “do I want another girlfriend?” There’s always the possibility that you’re only interested in this girl because you’re on the rebound. Not that there’s anything wrong with that, but it’s something worth taking into account. And if you do end up with this girl for the long haul…at least you know she won’t drive you into the poor house!