Sunday, February 11, 2018

When Money Meets Dating

When my ex and I broke up, I gave myself a six-month hiatus from dating.  I wanted to relearn how to be happy as a single person before I started dating again, in the hope that I wouldn't make bad relationship decisions to avoid being alone.

It ended up being easier than I had expected.  I had been unhappy in my old relationship for a long time, so the absence of the relationship's negativity in itself felt like happiness.  And there are big positives to being alone.  I like planning trips to France without considering what someone else wants to do, and I like always getting to pick the movie. 

Then my ex started dating again, and I got jealous.  I was doing so well with being single that I decided I didn't need to wait a full six months, so I signed up for an online dating site about a week ago.  It has been about as much fun as I expected it to be, with my previously healthy self esteem now as volatile as the stock market.  I check my profile more frequently than Twitter, and I devote way too much of my precious mental energy to the eternal question of "Why didn't she respond to my message?"

A friend of mine who is in a happily committed relationship keeps telling me that I should enjoy the process, which makes me kind of hate her.  Meeting new people is anathema to an introvert, and it is only made worse by the inherent vulnerability of trying to find someone who will like you enough to want to share your bacteria.  The best I can do so far is view this as a means to an end, and if I survive the process without hating it*, I will consider myself to have handled it well.

When I first subjected myself to this hell five years ago, I didn't really think about money.  I was a solid five figures in debt, so I didn't worry that someone was going to pursue me for my wealth.  But now, things are...different.  I'm on pretty solid financial ground for a forty-year-old, and assuming the stock market stops imploding, my finances are going to keep getting better very quickly.  My financial situation removes a lot of ordinary worries from my life, and it also lets me do a lot of things that most people can't.

One of the first things I've noticed with online dating is how different my travel history is from most people's.  "Where have you traveled?" is a common conversation starter online, and I feel uncomfortable listing off all the places I've been lucky enough to visit.  I abhor bragging, and it feels like that's what I'm doing when I say "Oh, I've traveled to all the places you have, but also 20 other places, because I am a rich doctor."  (I'm not actually that awkward online.  Hopefully.)  I know that this is a really nice problem to have, and this is not a complaint but rather a reflection, but it is still weird to me.

The bigger issue that arises with online dating is financial compatibility.  My city has a pretty shallow lesbian dating pool, so picking a partner isn't like customizing a sandwich at Subway.  What if I find someone who is cute and funny and nerdy but is terrible with money?  Or who wants to stay at home and play with the cats while I pay all the bills?  (Note to the internet:  If you are a queer woman who would like to pay all the bills while I stay home and play with the cats, my email address is on the sidebar.)

Dating is so frustratingly difficult. 

*I was going to make a joke about being murdered, but have you heard about the horrible murders in Toronto's LGBTQ* community


  1. You are thinking about all these potential issues when I think you should start with the basics: do I like this person. All that other bullshit you describe... it is important, but only after you’ve been dating a while. Do not sabotage yourself before you even start. You are likable. You have interesting things to talk about. It will be fine. (I have the doctor paranoia too — I.e Do they think I’m an asshole because I’m a doctor? Do they think I’m rich (and thus an asshole)? Do they want to steal from me? It goes on, so I definitely get it.)

  2. I find it helpful to remember that a first date can be forty-five minutes. Short enough that if it is mediocre, you have only "lost" 45 minutes. If it is terrible, you have a funny story. If it is wonderful, there is always ice cream. First interactions don't need to have the weight of an entire relationship.

    All of this spoken like a big ass extrovert. But I agree with OMDG. You are likable and you have the opportunity to find someone else who is likable and with whom you may or may not have some adventures.

    And you don't have to answer with every country. If you feel awkward, why not mention your favorite place you've been to or just the most recent one? Shorter answers means that the other person can ask more if they like the avenue of the conversation. One bite or kiss at a time.

  3. OMDG and ZJ are right about what to do. Small steps are good at first. Let any potential date learn about you a little bit at a time. I think you are an interesting person. If only I weren't married and old and far away and a man I would respond favorably to your profile.

  4. As a fellow introvert, I can only offer support for this part, and a listening ear. <3

  5. I agree with what's already been said.

    Speaking for myself, I can't even think that far ahead to focus on money. At this point, I'd just be happy to meet someone, anyone full stop. As long as the person doesn't any addictions, the money part can be taught/shared.

    Online dating can be rough if you don't have thick skin. I wrote about my own brief foray into those waters. It didn't go well for me but I hope you have more luck. Maybe I'll try a different site at some point in the future...

  6. I can only offer a suggestion for the specific travel thing - you can just say "my favorite place was X because...."

    But your real worries, i assume, are much broader than the specific. I have nothing helpful to say on the general concept of dating as an introvert, but I fully believe you'll be able to navigate this! Good luck!