Thursday, September 13, 2018

Musings on online dating

A friend recently posted on Facebook asking for "words of wisdom, musings, or general thoughts to share regarding online dating," and, probably suspecting that I might have some of the above, he tagged me in particular; that served as good motivation to dust off one of my mostly-written-but-hadn't-quite-finished-it blog posts from a couple years ago and finally git 'er dun.

Before embarking on a treatise about dating, I think it's important to acknowledge that waiting, not knowing when or if you will meet the person who may become your future spouse, sucks. It just plain sucks. Unless you've made peace with it, in which case, kudos to you. For a much better-than-mine essay about the realities of singleness (particularly as they're ignored by most married people on Valentine's Day), I encourage you to check out this article: (the original article was no longer available, but thankfully had a copy!)

Now on to my essay.

One of my friends and mentors went on 63 first dates before meeting (and later marrying) his wife. While I only reached one third that number of first dates, I figure that I still learned a few lessons worth sharing during my journey toward meeting my "forever woman".1

In typical Jeremy conversational fashion I suppose I'll begin with a disclaimer: these are my opinions, and I'm always right. Wait, wait, wait, what I meant to say is that these are my opinions, and I'm not always right. Dating looks different for everyone, so this is only a list of lessons I think I've learned, and attitudes that I found to be healthful along the way.

The most important lessons

I've made so many mistakes2 in my dating and relationship career3 (as well as heard plenty of stories from friends!) that I'm finding it difficult to pick one nugget of wisdom as the "most important" lesson-learned. If hard pressed, though, I'd say it's this: asking someone out for a date is exactly that. It's *not* a marriage proposal, or even a commitment to a second date. It's a single [pun not intended] date, with the goal of getting to know each other better to see if either person even is interested enough to consider planning a second date. Going into a date with this mindset relieves an unbelievable amount of stress. (For more on why I believe that, cf my previous blog post: Why I Kissed Dating "Hello", in which I highlight the awesomeness of this article: Why Courtship is Fundamentally Flawed by Thomas Umstattd. Also check out the book How to Get a Date Worth Keeping by Dr. Henry Cloud4, and a great essay I found called "How Christians Ruin Dating.")

For me, following the advice from Cloud's book (to ask out as many people as possible, so I could get to know as many different kinds of people as possible, so that I could better discover which traits actually were important to me and which weren't) primarily took the form of online dating on eHarmony. But in addition I also asked women out at church (which in my opinion is a better place to meet people than a bar, but again that's just my opinion), gave my phone number to at least one waitress, and petitioned countless friends if they knew anyone they thought might be a good match (special shout-outs to my neighbors Megan and Michael, and my friends Maggie and Christine, who each took me up on that invitation and set me up on dates with some of their coworkers and friends!).

Living into my philosophy of "it's just a date" took away almost all of the sting when facing rejection. Many of the women I asked out said "no," and though I wasn't very skilled at receiving that early on, after a while it became much easier. Especially with online dating, when someone I messaged didn't respond or blocked me, I learned pretty quickly just to move along and not take it personally. Remembering all the women I myself blocked because I didn't like something on their profile made this moving-on much easier. Eventually I figured out that I should never have to convince anyone into going out with me. If they're not in the same mindset (for example, maybe they were in Camp Courtship), then the time isn't now. If she said "no," I [eventually] learned to be gracious and say "thanks" anyway. While certainly not everyone appreciates being asked out, I *think* most people (both genders) at least find it flattering (as long as you're not creepy or a douche about it). As one woman said to me, "it's always nice to be taken out and treated like a lady."

First dates

For the ones who said "yes," where we did get to go out on that first date: I learned that I should avoid going into the first date with our grandchildren's names already picked out. Instead I found it beneficial to set my expectations only on things within my control. For example, if I was meeting my date for dinner, then my expectations going in would be, "I expect to eat dinner." Notice what's not on my expectation list: having a great conversation, setting up a second date, falling in love, etc., because all of those are beyond my individual control. This comes with the added bonus that, if we did have a great conversation, and set up a second date, then I exceeded my expectations! Who doesn't like saying "that went much better than I thought it would!"? To be clear, this doesn't mean I would go into a date with no hope - certainly I hoped to meet someone I could enjoy spending time with! My point is that I set my sights on what was within my own power to control, and not dependent on anyone else.5

Contrary to what popular culture says, I thought it absolutely was important to talk about religion on the first date, at least in a broad sense. Diving into deeply sensitive and highly charged theological issues wasn't on the menu, but asking what church she went to, how involved she was or wasn't, and what she valued/disliked about that church, I considered to be fair game. There aren't any right answers to those questions, I just think it's important to make sure both people are at least playing in the same ballpark6, even though it's unlikely we'd agree on every minor theological issue that would come up in later conversations.

Some first dates went terribly. Sometimes conversation was awkward, we couldn't find any common ground, or I saw some other red flag.7 My solution was simple: I didn't ask her out again, and prayed to God she didn't mention "getting together again" while we were still talking in-person, before I could safely ignore her messages from the comfort of online. Was that the most mature solution? Nope. I'm not proud of it. I should have learned better from one girl I went out with, who, after I asked for a second date, politely said, "no thanks, I don't think we're a good match," and there were no hard feelings. Eventually I got better at this, but to be honest my preferred method was avoidance.

Other first dates went swimmingly. Or at least, "fine." My general rule on a first date was that if I saw no red flags, I'd 'make the ask' for a second date. Like I said earlier, sometimes my date would decline, but usually she'd accept. My reason for this very conscious decision, is that on date #1 most people (men and women) are overthinking and overanalyzing and as a result not really being themselves. On a second date, that awkwardness is out of the way, making more room for real conversations that matter. So if I thought she was at all interesting and again, no red flags, I'd try to set up that second date right away at the end of the first date, before we parted company.

Second dates

Surprisingly, at least to me, more than a couple times I'd ask for the second date, she'd agree, and then hours or days later, she'd cancel on me. I never figured out if it was something I said, or if it had nothing to do with me at all. For example maybe she, like me, was going on dates with multiple people at once, and maybe another one of those dates took off into an exclusive dating arrangement. I'm also not unwilling to consider that perhaps she prayed, God answered, "not him," and she moved on.8 Who knows. Point being, cancelations happen, and you move on.

A related word on interpreting cancelations. I learned that when someone (I believe this applies to both genders) cancels or declines your plans, and doesn't offer an alternative time - for example, "I'm not available Sunday" - that should be interpreted as "I'm not interested." Alternatively, if s/he offers an alternative - for example, "I'm not available Sunday, but Monday could work" - that should be interpreted as a positive sign, because they are trying to make something else work. This applies when asking someone out for a date (initially or for subsequent dates), as well as acquaintanceships where there is no intention of romance.

I also want to call out something I mentioned in passing two paragraphs ago: in my opinion, it's perfectly acceptable to schedule dates with multiple people, up until one of those dates turns into an exclusive dating arrangement (by whatever label you want to call it: dating, relationship, courtship, exclusive, etc). My friends and I call that moment the "DTR": "define the relationship." I'll again commend the article I mentioned earlier, Why Courtship is Fundamentally Flawed by Thomas Umstattd, which delves further into that issue, but I'll summarize it with this quote from the article:

When my grandmother dated in middle school (yes, middle school) her parents had one primary rule for her.

The Primary Dating Rule: Don’t go out with the same guy twice in a row.

So if she went out for soda with Bob on Tuesday, she had to go to a movie with Bill on Thursday before she could go to the school dance with Bob on Saturday.

That sounded crazy to me. So, I asked her the rationale behind it. She explained that the lack of exclusivity helped them guard their hearts and kept things from getting too serious too quickly. The lack of exclusivity kept the interactions fun and casual. "The guys wouldn’t even want to kiss you!" She said.

Lastly, regarding second dates, third dates, fourth, etc: I think it was my friend Pam who taught me, "always compliment her on something on each date," whether that be her hair or smile, and also non-physical traits, like, "you seem cheery today!" or "that's a fun outfit." I admit, I never really got good at this, I'm just passing it along because it seems like sound wisdom.

The "right" person

I've long held to the belief that there is not one and only one specific "right" person for me; rather there are a bunch of different right persons, and life together with any one of them could look beautiful. Vastly different, because each individual is unique and therefore each possible relationship equally unique, but nevertheless each carrying potential for a lifelong partnership. For me, I replaced the question, "are you the right person?" with, "are you a right person for me?" And equally important, "am I a right person for you?"


Years ago, I told my friend Joe that I wouldn't consider my life complete or successful if I never had a family. He challenged me that I was putting God into a box by dictating to God my conditions for the only possible way I would be happy, rather than having faith that God could bring happiness into my life even if I remained single forever, or never had kids. This provoked a many-years-long prayer, "God, please prove Joe right and prove me wrong."

Eventually, I more or less got to that point, where I could see the joy in my life's future, regardless of marital status. It helped knowing I could also adopt kids as a single parent, if that was the direction life brought me.9 As part of this journey, I spent considerable time examining my own emotional health and ensuring that I was ready to date / seek a relationship. This included making sure I was "over" previous relationships, or at least, as "over" it as I could be.

Not everyone I dated seemed to hold this same philosophy. Twice it happened that a woman I went out with decided she wasn't over her ex. The first time this came up, fortunately we'd only had one date, and so while I was disappointed (we'd had a pretty great first date), it wasn't emotionally crushing. As for the second woman who did this, we'd had several dates and many lengthy emails, and I had fallen for her. Coming to terms with her rejection was a very painful and emotionally expensive experience.

This led me to a very important lesson: before asking anyone out on a second date, double check that they're emotionally available.

To quote from one of my absolute favorite books, Boundaries by Dr. Henry Cloud and Dr. John Townsend:

Dating is a means to find out what kind of person we complement, and with whom we are spiritually and emotionally compatible. It's a training ground for marriage. This fact causes a built-in conflict. When we date, we have the freedom to say, at any time, "this isn't working out" and to end the relationship. The other person has the same freedom. What does this mean for the person who's boundaries have been injured? Often, she brings immature, undeveloped aspects of her character to an adult romantic situation. In an arena of low commitment and high risk, she seeks the safety, bonding, and consistency that her wounds need. She entrusts herself too quickly to someone whom she is dating, because her needs are so intense. And she will be devastated when things don't work out. This is a little like sending a three-year-old to the front lines of battle. Dating is a way for adults to find out about each other's suitability for marriage, it's *not* a place for young, injured souls to find healing. This healing can best be found in non-romantic arenas, such as support groups, church groups, therapy, and same-sex friendships. We need to keep separate the purposes of romantic and non-romantic friendships.

There's also the issue of physical availability. I chose to pursue long-distance dates with women in southern Minnesota, Iowa, India, and Australia (Skype and Facebook Messenger calling and FaceTime are all wonderful inventions), and even though long-distance relationships have their own set of challenges (time zone differences and unreliable Internet connections being among them), I found these to be some of my most rewarding and exciting relationships. You might ask, "why on earth would you want to date someone from halfway around the world???" That's a fair question, with a very simple answer: the accents. Also because my friend Ann started dating her now-husband while they lived in different states, I figured why limit myself to only my city? But mostly: the accents. As for the question, "how would that work out?", the answer is one of us would have had to consider moving. For example, India Girl had already planned on moving to the US in the next few months/years; and as for Australia Girl, well, I confess spending a few minutes on Australia's immigration website looking at what their requirements were.10

Beyond ensuring my own emotional health, part of my "making sure I'm ready to date" posture was making sure I actually had room in my calendar to go out on dates (time availability), and that, overall, I was happy with my life. This is because, as my friends Hannah and Richard pointed out to me, being in a relationship brings out all the stuff you need to work through, and if I'm not happy with my own life to begin with, how should I expect to bring someone else into that? (I bolded that because on reflection I think that tidbit might compete with the "most important" lesson I highlighted at the beginning).

Rejection, and Prayer

During my dating adventures I faced a lot of rejection from nearly all stages (the only rejection I didn't get, fortunately, was when I finally proposed to Alissa - she said yes :). Early rejection on the dating site wasn't too traumatic - like I said before there were plenty of women whose profiles I hid for one reason or another, and some who attempted to initiate communication with me and I chose not to respond. Even asking someone out in person and being declined, kinda stings but after enough practice I found out it wasn't the end of the world.

What did start to hurt was going out on a really awesome date with someone I was really excited to get to know, and then being declined for a second (or third, or fourth) date. What stung even more, was [at least twice] not being chosen in a competition I didn't even know I was competing in: between me and her previous boyfriend. And what stung the most, was falling in like over three weeks of dating then ultimately being rejected because I refused to agree that homosexuality was sinful, which she decided was a deal-breaker because "how would we raise the children?" (this is a true story).

I think it's true for me to say that, in the aftermath of every rejection, I prayed. Earnestly, passionately, tearfully. "God, when? When will I finally meet Her? If not <most recent heartbreak's name>, then whom?" I also prayed for miracles of emotional healing, for God to dull the pain or take it away. This did happen a couple times, where, having emotionally exhausted myself the previous night, I woke in the morning with the ability to say (and mean it), "if that relationship isn't going to be, then I'm excited to meet the woman with whom it will work out." This hope for the future came from recognizing my own pattern: every time I fell for someone, I found her to be in some way even more amazing than the last relationship. Therefore I supposed that whomever God might have me meet next, I would likely find her to be yet more amazing still.

Keeping a focus on prayer while dating is something I wish I'd done better at. I mean, I didn't completely suck, but I could have done better. It's weird to think about online dating in such terms, but I tried (when I remembered) to ask God into that experience, helping me connect with the women who could help me grow as a person (or eventually, connect with the woman I'd marry), and to avoid (or be avoided by) the women who maybe weren't as great a match for me.

Two months before I met Alissa, I had a dream in which my future wife (unknown to me at the time) challenged me with this question: "how will you help me grow closer to God?" It was a fascinating question, one I actually had considered before, but had back-burnered. I think it's an important question to ponder in any human relationship.

Why I chose eHarmony

Before eHarmony, I tried a few other online dating sites without much success.

OKCupid is free, but my experience was that users weren't serious about pursuing romantic relationships, they were on the site more to find friendships or email buddies, neither of which were what I sought.

ChristianMingle gave me my two worst dates of my life. (feel free to ask me about it, I think they're funny to talk about now) I never used myself, but having heard negative reviews from friends and a coworker about the quantity of fake profiles, I wasn't interested.

I ultimately chose eHarmony because, despite it being expensive, I'd heard one first-hand success story (a former teacher of mine met her now-husband on eH), and a few second/third-hand success stories. It was the right decision for me.

As I got into using eHarmony, I discovered other perks I liked about eH over the other sites. The biggest perk, for me, was that instead of writing "cold call" messages (in other words, having to create something witty and engaging to write to the other person, based on nothing besides what can be read on their profile), eH provided what they called "guided communication." This process started by sending one's potential match five multiple-choice "get to know you" questions, like, "on a Friday night would you rather... Go bowling, Go to the movies, Hang out with friends, Sit home and relax", or "what's your idea of a romantic date... A walk on the beach, a candlelit dinner, making dinner together, a movie", etc. eHarmony provide 20-30 questions from which to pick, and then the other person will either respond to those by answering them and sending five questions back, or they'll never be heard from, in which case I didn't waste HOURS agonizing over writing a cold call email (seriously, it literally took perfectionist me hours to compose even the shortest of messages on OKC).

After volleying the 5-Qs back and forth, the second guided communication is "makes & breaks" - a multiple choice list of attributes each person sees as deal-makers and deal-breakers. Generally my experience was this stage was a formality, because everyone's lists more or less looked the same. Every now and then I saw something interesting, but typically this stage was more importantly a step to say "yes I'm still interested in getting to know this person."

The third stage is short/long-answer questions, like, "describe your faith," or "what's your relationship like with your parents," or "what's an important lesson you learned from a previous relationship." Again each person chooses which questions to send, or there is a place to write custom questions.

Finally, after both users answer the short-answer questions, eHarmony allows the initiator (whomever sent the first set of five questions) to write an actual "eHarmony Mail" to the other person, and by this point I found there was almost always at least SOMETHING interesting from the question & answers to make message writing easier and feel more natural. Also I valued that, by this point the other person was at least somewhat interested in hearing from me, because otherwise she wouldn't have spent her time answering and sending questions back and forth.

In addition to providing this guided communication, eHarmony's other major selling point (for me) was that they only gave 5-10 matches a day; after those 10 people, you're 'done' for the day. This was huge. A drawback I think of Match and others is that there's never a finish line, it's always, "but what if my perfect person is on the *next* page of search results?" eH took that worry away by giving me an ending point for each day.

Lastly, I'll simply state that I had great conversations with almost every woman I went out with from eH (if memory serves, I think I only had 1 "bad" date from eH). Even if we didn't have a relationship in our future, we still had good talks and I learned much along the way. In at least one case, after deciding we weren't interested romantically, we maintained a friendship for a year or two, sharing new dating stories with each other and asking advice. As well, two of my now-favorite musical groups (Two Steps From Hell, and similar solo projects from Thomas Bergersen) were suggestions from "girl #3" many years ago. What I'm trying to say is that the matching algorithm eH used seemed to be pretty good at pairing me with women with whom I'd at least have *something* in common; might not be the case for everyone who uses their service, but it was true for my experience.

Advice about online dating in general

Perhaps the most "real" advice I received about online dating came from my friend Ann, who told me I'd need to devote at least an hour every day if I was going to be serious about it. This seemed excessive to me when she first said it, but Ann was absolutely right; while reading new profiles took only a few minutes, responding to communications (whether the 5 questions or short answer essays or especially the full-length eH mails) could easily consume an hour or more each evening. Possibly some might call that time wasted, though I'd contend it was more of an investment (in addition to the financial investment I was already making in eHarmony). Any case, I mention this because the time requirement was, to me, one of the most surprising aspects of online dating.

A couple years ago, in reflecting on my own journey, I made a list of other practical advice I'd like to offer to my friend and anyone else embarking on the online-dating road (though admittedly most of this is just reiterating the standard stuff you'll find in other opinion pieces around the web).

  • plan to spend 2-5 hours in order to set up a quality dating profile; also, the more pictures you upload, the better; choose also a variety of angles & environments - headshot, torso, full-body, group shots with friends, etc
  • once you start communicating with your matches, plan to spend at least an hour a day or more on answering questions/mails, and looking at new matches. I never believed my friend when she told me how much work online dating takes, but it does take a serious time commitment. That's not to scare you away, just letting you know it's not something that will only be like 5 minutes a day.
  • dating can become expensive if you let it; when suggesting a date, you don't always have to do dinner/lunch (and even then, it's up to you if you pay for both of you or go Dutch, as long as that's communicated in advance). You can also do activities that are free and still fun, like walks in the park, window shopping around the mall, outdoor street/music festivals/shows, etc.
  • have standards, but be open to going on a first date with someone who may be on the periphery of what you thought you were interested in. I'll once again commend the book How to Get a Date Worth Keeping by Dr. Henry Cloud.
  • try not to take it personally if someone you were interested in doesn't respond, or blocks you. I'd guesstimate that less than 5% of the women to whom I sent 5 questions ever responded, and of those only a handful resulted in an actual in-person date. It's a numbers game. One of my guy-friends joined eH and then was SUPER picky about who he'd send 5Qs to (like, on the order of one woman a week). I wasn't surprised when he complained to me that he wasn't having any success. On my end, I would send 5Qs to anyone I thought looked even remotely interesting, probably a few dozen each week. Like I said, most didn't respond, but of the ones who did and with whom I messaged and eventually went out, we had a really great time.
  • following on to the above two points, if you do see a [figurative] red flag on someone's profile, it's okay to block them and move on; this is also why I didn't take it personally when the same happened to me, because who knows what red flags she might have seen on my profile - you should never have to try to convince someone to go out with you.
  • if, during a first date, you decide you're interested in a second date, say so; and try to pick a time before ending the first date. While there is the risk that a lot of people aren't good at saying "no" (so they might cancel later, or might cancel for reasons not at all related to you, like another date they went on has developed into something more), I still found it very effective to "make the ask" for the second date before ending the first one.
  • try to avoid putting all your hopes and dreams for the future on one person; it's unfair to both you and them.
  • find a reasonable-to-you balance between going on dates, and investing time in your existing friendships and family. They're the ones who'll still be there to reassure you when a date/relationship goes south.
  • lastly, something I didn't do and in retrospect wish I'd done more of: trusting God in the process. I wish my prayers were less like "when will I meet my 'one'?" and more like, "please introduce me to the right people at the right time to develop healthy connections, and help me to learn and better myself along the way." In other words, I wish I could have looked at dating more as a journey of self-discovery / self-improvement, rather than a destination to which I needed to run.

Those are *my* thoughts ; some may work great for you, others may not, and that's okay. Do what makes sense for you.

That's probably a high enough word count for this post. I've oft been accused of being too wordy, so, my apologies for not taking time to write a shorter essay.

1 My friend Anne introduced me to a turn of phrase I find just beautiful: "forever man" and "forever woman." It's inspired by a Dixie Chicks song called "Lullaby."

2 When I use the word "mistake," I'm using this definition:

"It is a decision in which one or more of the factors is known to be dangerous, or poisonous, or compromising, but which we calculate will not keep us from achieving our goals. But when there is no foreknowledge of such factor in evidence, can it be called a mistake? If you walk out on an empty field, and the ground suddenly gives out beneath you, and there was no way to predict it, was any part of your decision making a mistake? No."
- Admiral Cha Niathal, from the book Star Wars: Fate of the Jedi: Backlash by Aaron Allston

Under this definition, a lesson-learned need not ubiquitously be predicated by a "mistake" (though many certainly are). In other words, when I say "mistake," I mean not "I should have known better," but rather, "I did know better."

3 When I say "career," I mean it simply as a realization and acknowledgement that I am the single common thread in all of my past failed relationships, and therefore it's worth exploring whether and how I grew from those experiences. Some of those lessons are helping me now, in my married life.

4 Incidentally, Dr. Cloud also wrote Boundaries, which is another favorite book (and discussion topic) of mine.

5 The same rule comes into play in many areas of life. For example, if applying for jobs, don't set a goal/expectation of "I will get a job within the next month." Rather, set a goal/expectation that "I will send out X number of resumes in order to give myself the best chance at landing an interview, and then a job." See also the "practice expectation management" paragraph on my Life Lessons Learned blog post.

6 See what I did there? That was a sports metaphor.

7 When I say "red flag," I mean "deal-breaker." Like, they smoke, or are codependent, or have no ambition for their life (not the same as still searching for a dream job - that shows that there's at least some thought given toward the future), or they're vegetarian and they would insist on you becoming vegetarian, too. A red flag isn't the same as a yellow flag, which might be something like they still live with their parents (there might be a logical, perfectly healthy reason), or they have crazy work hours (this only becomes a red flag if they aren't willing/able to find some way to prioritize time for a relationship later on, should the dating relationship head that direction).

8 Once - and only once - I prayed and got this same answer from God myself. Meaning: I'm more willing to believe someone now if/when they say, "I prayed about it and I don't think we're meant to be."

9 In fact on my 6-year plan of post-it notes on my basement wall from before I got married, I had a post-it note labeled "Adopt!" under the 2021 label. Whether or not I was married by then, I wanted to start creating a family.

10 Back in the day you could get into Australia just by committing a crime somewhere else in the world; turns out they're a little more picky nowadays, and generally frown on criminal records. I found that funny.