Dater XY: The Post-Sex Guilt Date

A woman I’ll call The Chewer (it’ll make sense soon) and I first messaged each other shortly after things ended with The Teacher over a two months ago. We hit it off as she was about to relocate to my town, and had attended the same university. We decided to meet for drinks after she finally moved up and got settled in. Before we got to that point though, I started going out with a few other women and wanted to see where these potential relationships went. I messaged The Chewer and she thanked me for my honesty and I went about my way.

As it turned out, most of these dates were ho-hum and never amounted to much of anything. I did briefly hit it off with The Marathoner but that ended as quickly as it started. So, my schedule suddenly freed up, I decided to message The Chewer to see if she was still interested in getting a drink. She was so we planned to meet after work two weeks ago (shortly before I went out with The Lawyer).

Had I messaged her because I had burned through my other “options”? I suppose that’s a cynical way to look at things but not entirely untrue either. While The Chewer and I did have a few things in common, I wasn’t particularly drawn to her and didn’t find her to be all that attractive (not ugly by any means though). Still, as a recent transplant myself, I was excited to meet someone from my alma mater.

Things changed when she arrived to our first date, though. Unlike MissRepresentation, she came dressed to impress and had a smile to match. Things were going well and as the pub was starting to get loud, I suggested we relocate to a nearby restaurant where we could actually hear each other talk.

After dinner, I waited with her for a cab before a kiss goodnight and a promise of a date in a couple weeks when our schedules realigned.

That came about this past Friday. We met at a local BBQ joint. While the service and food left a lot to be desired, we managed to have a good time getting to know each other. This being our second date, we were at ease with each other, but I wouldn’t say the conversation was especially exciting:

Her: So are you a Republican? I know a lot of guys down south are Republican.
Me: Well, no but it’s complicated. I consider myself a progressive libertarian.
Me: So did you ever go to that $5 all you can bowl alley near campus?

After we paid, I suggested we go back to my place for some wine.

Once back at my place, we continued talking with increased flirting leading quickly to putting down/spilling our wine glasses. Before we knew it, we had made it to my bedroom and were having sex. The sex was okay — not great but not horrible. Mostly, I chalked it up to not knowing what we both liked as opposed to absolutely no sexual chemistry. First time sex can be a little awkward, right? Before she left for the night, I invited her over the following night and offered to cook dinner. She agreed and we kissed goodnight.

Saturday flew by as I went shopping for dinner (pan-seared crab cakes and asparagus!) and we were, sadly, eating in no time. I say sadly because The Chewer is, yep, an open mouth chewer/smacker. $@%$@#^@#@$%@#!!!!! Easily my biggest pet peeve. When I encounter people like this, it takes every ounce of strength to not yell at them.

Luckily, though, she thoroughly enjoyed the meal and ate it quickly. Not wanting to end things quite yet just because of her eating habits (Maybe it was an off day? Maybe she has a jaw-hinging issue? I hoped), I introduced her to “The Following,” which we watched for a little while before falling asleep on the couch together.

As with the night before, she needed to leave to get sleep before work the next day so we tentatively planned to see each other this weekend.

And here is the quandary. I’m not sure I really want to see her again. Why? Well, it might seem like a small thing, but I really can’t stand people that chew loudly/with their mouths open. That’s not all, though. Having gone on three dates now, I realize most of our connection ties to our shared alma mater and love for Southern foods and not much else. Talking about professors and the best collards we’d ever ate became the awkward silence savior and was increasingly being used. And then, there’s also the lack of undeniable sexual chemistry.

When to progress sexually in a relationship is a common debate, including in one’s own head. “I want to have sex with him/her but if I have it so soon, will they just leave?” This is why I feel obligated to see her again, because I don’t want to be THAT guy, the guy that left after he “got laid.” Granted, she deserves better than a one last “I feel bad that we had sex and now I want to bail” date but I nonetheless feel guilty and unsure of what to do.

As of now, I’m undecided, but I feel like the best option is to let her know I think it’s best to go our separate ways and chalk this up to potentially moving too fast or just an overall lack of sustainable chemistry. Are there any other options, besides the aforementioned guilt date?