How Long is Too Long for Me to Be the One Pursuing a Guy?

by Gena Kaufman

Our awesome reader is going after the guy she wants, but she's not sure if it's time to throw in the towel. Let's discuss.

She writes:

This fall I had been trying to get together with this guy I know through some past coworkers. We had hung out a couple times in a group setting and seemed to hit it off, but we didn't end up getting together again until November. I wasn't sure if it was a date, and as soon as I met him he said, "I asked other people if they wanted to come, but they are busy. They may meet us for drinks later." OK, not a date. We went rock climbing together, which was fun, and then out to a bar, where we found out the people who were maybe going to come couldn't. We ended up staying at the bar for four hours talking! I was having a good time, and toward the end of the night, he leaned in and kissed me. We kissed a couple of times before we left the bar and he kept saying stuff like "I'll have to find another adventure for us." I paid half the bill, and he kind of protested but said he'd get next time. We kissed again and parted ways. So, it was a date?...

He texted me a couple of days later, but we didn't plan a second date. About a week after our first date (if it counts as one), I invited him out for casual drinks with a group of people, but he said he was busy at work. A little while later I asked if maybe he had time to get together before Thanksgiving. I didn't hear from him, but then early Monday morning he said sorry for the horrible delay, he didn't see the text, but he wasn't sure if he could go out because he needed to get a lot of work done before the holiday. I let it go and we talked in December. A mutual friend texted both of us asking if we wanted to go out to drinks after work, which I replied yes to, but he never answered.

It's been over a month since we went to drinks. He's always friendly when we talk, replies to my texts usually right away, and he's the one who initiated the kissing and texting me after our first kind-of date. But since then it's been me going after him, which I don't mind, but I'm losing confidence. I like this guy a lot, which is why I haven't given up, but should I now take his silence as a hint that he's not interested anymore? Is there a way to just straight-up ask him without scaring him away?

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Let's start by saying we all salute you for being unafraid to be the one pursuing a man. It's confident, it's cool, and you should definitely keep doing it in the future.

Just not with this guy.

I hate to say it, because I know you like him, but I just don't think this guy is that into you. He obviously has at least a little interest since he kissed you and continues to stay in touch at least somewhat, but I think he was either just trying it on for size and decided you guys weren't a good fit, or he's keeping you as his option on the back burner in case he gets lonely later. Either way, that's not your fault, and it's not what you deserve. It's awesome for a woman to be the pursuer, but at some point, a guy has to return the efforts, and he's just not. I think it's time to write him off.

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If you absolutely must make one last attempt (which I don't recommend since you've already given him plenty of tries to take the bait), I'd at least make it very straightforward. By which I mean, don't ask him to a casual hang-out with friends, and don't let him give a vague answer about doing it some time "later." Ask him to hang out one-on-one, and if he can't commit to a specific date, forget him.

There will be plenty of guys who really do want to go on adventures with you. I hope your experience with this one guy won't stop you from going after other men. You're just way too fun to waste any more time on a guy who isn't giving you anything back.

Do you agree that it's time to give up on this guy? Or do you interpret the situation differently? Sound off!

Have your own dilemma to discuss? Email me at smittenbloggers@gmail.com. I'd love to hear from you!

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