Should dating her feel like a rollercoaster?

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kybo0 asks:

It’s been a month since we’ve been dating. I’m 24, she’s 37. I have been doing my best to be a challenge and be honest. This week, I’ve felt up and down. Her texts have periods where she seems less loving, less sexual, or that she can’t be bothered. I send about 7-8 texts a day. I stick to the rule of sending equal or one less text than her. 

Today, she said she would come and meet up for a bit on her break. She did a no-show, then continued to speak as if she was going to meet up. Now, she has mentioned that she is going to dinner “with a friend tonight” but has been a tad bit ambiguous. I trust her, but after the general feeling I’ve got from her texts, a part of me is unsettled. I’ve just ignored it and buried myself in the gym and hobbies.

I also feel like I’ve fucked up. We got drunk last week and she told me that she loves me. I said I didn’t want to say that right now. When I do, I want it to be right. But, I told her that I do think about her in the morning and before bed. 

How do I handle this? I care about this woman a lot, but I feel like I’m strapped on a rollercoaster. I forgot how much work dating is.

Should I feel this way?


Demetrius says:

My first question has to be whether or not within the 4 weeks of dating that you’ve noticed a pattern of behavior you didn’t like before, or after she told you that she loves you. Because, I get that you’re younger and all, but you have to see how tough it is to tell someone you love them, not have that love reciprocated, and then try to carry on like normal.

First, let’s talk about your texting. The amount you text, and I’m using you generally to refer to all people, not you specifically, doesn’t have to stick to any rules per se, but your texts should be one of three things:

  1. Good morning and good night texts
  2. Substantive
  3. Just saying hello/Thinking of you texts

The quantity with which you text and whether or not it’s okay isn’t something that can be easily made into rule, but if you’re texting someone it should be one of those three things. If you’re texting just to stave away the boredom of your day, you’re doing it wrong. Maybe the commitment to texting 7-8 times a day with someone you’ve known for less than a financial quarter is a bit much, especially if you aren’t saying anything in your texts. It isn’t the volume alone that bothers people about texting, it’s what’s being said. If you lead with “hey, how’s your day” for 30 days in a row, you’re probably the person who texts too much. If each time you text it has substance, whether it’s date planning, or discussing a topic you both actually are interested in, you’re the person whose texts people look forward to.

With the texting out of the way, let’s get down to it. Based on the way you laid things out, it seems to me that her being hot and cold is a direct reaction to her telling you she loves you and you saying you didn’t love her.  If that truly is the case, she will probably be ending things with you very soon. She’s a 37-year-old woman dating a 24-year-old man, who she loves, who doesn’t love her, but texts her 56 times a week. I’m sorry but nothing about this scenario is saying to me that she’ll suddenly warm up to you. Unrequited love is not something you just get over and move on from. She’s planning her exit from this situation shortly, and while you may trust her, I can almost guarantee that the “friend” she’s having dinner with is more than just a friend. He might be an old flame, or a new guy she’s meeting for a casual date, but trust me when I say your days are numbered. As they should be, if I’m being honest.

Even if I’m wrong about her being hot and cold with you because of the whole unrequited love thing, she is still not a good fit for you. No, it’s not just because she’s older, it’s because you aren’t a good fit. Your communication styles are different and her communication style makes you insecure. Also, more importantly, YOU DO NOT LOVE HER. You’re not strapped to a roller-coaster, you’re dating someone who seems like a good match for you, but isn’t, but she’s not a bad enough match where you immediately know you should end things. Even if you’re the type who thinks that you should continue dating someone until you maybe, might develop love for them, the way she texts makes you insecure and you feel like you can’t be yourself when communicating with her. That alone seems like a good indication that maybe you aren’t a good fit for each other.

You’re feeling unsettled, stressed, anxious, and just plain uncomfortable with dating her. You didn’t mention, not even once, why you like her, or what draws you to her, or anything that remotely sounds like a “good” part of dating her whichI think that says a lot about your compatibility. Maybe she’s very attractive, very dynamic, and very much not a good fit for you. Dating requires a lot of work, but if that work doesn’t feel rewarding, why do it?

Good Luck Out There.

Demetrius Figueroa

Demetrius is a sex, dating, and relationship writer based in Brooklyn.

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