Name: Perplexed Man |  Location: Chicsgo , IL |Question: I have been out if the dating loop for a while, and I’m having trouble deciphering whether a woman is generally interested in me, it she’s being nice. First date seemed to go well, and throughout the next week we exchanged fun and somewhat flirty (more on my end) texts. When I asked her out for a second time she said she should be available. The day of the date, she asked for a raincheck, that she couldn’t make it out because she was tired and she was going on vacation. Since she didn’t follow that up with any indication that she wanted to get together when she got back, I just wrote her off as not that interested in me, and moved on. But she continued to text me (unsolicited) everyday she was on vacation. I would think if she definitely wasn’t interested, she wouldn’t text me while she was on vacation. So I’m wondering: should I bother asking her out again? Are women still in that ‘the man must make EVERY move mode’ or am I overthinking? |Age: 41

You’re not over thinking. She’s waiting for you to ask her out. I’ve mentioned this before, but I think there are a lot of people out there – men and women – who do something similar. They go out with someone once or twice, then cancel the second or third date. Then they sit back and wait for the other person to follow up with them  and ask them out. Often times, but not always, it’s a test. They want to see how interested the other person really is. They cancel plans, truly believing their ill or sleepy or busy but actually could go meet the person. They’re waiting for the other person to chase them to some degree.

One of two things is going on here:

1. She’s genuinely interested, but stuff came up and she couldn’t go out with you. She’s texting you to show you she’s still interested. In her mind, she’s served you the ball and showing you she’s in to you. Now she’s waiting for you to volley back and ask her out. After a certain point, she’s going to do the whole “Sheesh! Why isn’t he asking me out??” thing. So ask her out. It’s not worth engaging in a pissing match. Life is just too short for that.

2. She’s not terribly interested in having a relationship with anyone, but thinks she is. She’s keeping you around for the attention you provide.

The problem is that you won’t know which it is unless you ask her out again.She’s either going to jump at the chance or stall. If she stalls, you have your answer.

Are women still in that ‘the man must make EVERY move mode’ or am I overthinking?

Yes, they are. They’re still in that mode. At least some of them are. This woman truly believes – and to some extent she’s correct – that’s she’s making effort and putting herself out there. I think it’s ridiculous to engage in some sort of back and forth thing. At this point, she should just suggest you meet up when she gets home from vacation. I’m truly hoping she’s not one of those people who gets exasperated every time the text alert bell rings and wonders why you just don’t call her. In those cases, ladies, if it’s REALLY important that you talk on the phone, call them. It’s just so silly to be sitting there responding with the exact same behavior that has you annoyed. I think these women are waiting for permission to take the lead or assert control.

You shouldn’t and don’t need permission to express yourself. As we’ve said so many times, men will choose the path of least resistance. We know that. So rather than act surprised when they do what we know they’re going to do, take action.

In the OP’s scenario above, both people are wondering who should take action and falling back on outdated gender rules. There are no more gender rules anymore, folks.  You have to stop playing by them as if they exist. They don’t. There’s just no time for that anymore. Everything about how we connect and communicate now revolves around brevity and speed.