In The Mathematics of Love author Hannah Fry shares a lot of practical dating advice designed to optimize dating outcomes for those who are looking for an ideal partner. One of the biggest bits of advice she gives is founded on Optimal Stopping Theory, and Hannah Fry gives a neat formula for calculating the best time to stop dating and choose a partner (Fry, 2015). You’ll have to read the book if you’re interested in the formula and all of the other good bits of advice on dating, but the over-simplified gist of Optimal Stopping Theory is that your best option for a life-partner will likely come after the first third of your dating years (Christian & Griffiths, 2016; Fry, 2015).
So, if one has been dating since the age of 18 years and expects to give up on dating by the age of 42 years, that’s a 24 year dating life. According to our over-generalized Optimal Stopping Theory, that means that 8 years into that dating life, the individual should be choosing a partner if that person wants to select the best possible partner. According to this individual’s dating life-span, the person should be choosing a partner at the age of 26 years old.
Of course, this estimation excludes a lot of information and context. In an age when Millennials are marrying later and have different expectations for relationships, we can expect that romantic relationships will take on different characteristics than former generations (Manning, Smock, & Fettro, 2019; Martin, Astone, Marie, Peters, & Elizabeth, 2014; US Census Bureau, 2018). Many other factors need to be accounted for when choosing a partner, but Optimal Stopping Theory does support some conventional wisdom. As a friend recently told me, “Don’t wait too long.”
In 2018, my attempts to optimally stop my search for a significant other were unsuccessful. I attributed this to a small sample size and decided to give online dating a chance. I signed up for a year of online dating on one website, and I was immediately met with a variety of conundrums.
Online dating sites have a variety of ways in which one can start a conversation. Instead of sending a message to everyone who captures one’s attention, there are often more ambiguous options that can imply a variety of things (e.g. pleasant disposition, a desire to start a conversation, a passive pleasantry, etc.). Think of sending a “smile” emoji or a “like” to someone or someone’s published content on social media sites. One big difference between a “like” on social media and a “smile” on an online dating website is that in the case of the former it is easier to assume things.
One can often give into gut feelings. ‘She likes me!’ may be a easy thought to have. ‘He’s open to dating me…’ may be another. ‘That’s nice…’ or ‘No thanks…’ or ‘Nope…’ may be other thoughts. In my experience, “likes” and “smiles” mean one is open to starting a conversation, but ultimately, it’s hard to define or attach definitive emotions to these social media tools.
It’s nice to think people can easily survey a field of potential relationships and take or leave options as they choose without consequence, but is that a realistic thought? As I initiated conversations there were typically 3 defining points – the initial messaging, movement to another media of communication, and meeting up or ending the conversation.
- Initial messaging or ending the conversation
- This is the stage when the conversation starts. It can be characterized by a lot of questions with long, explanatory messages or by short, flirty messages. It depends on a lot of factors, but in my experience a lot of these initial conversations fizzled out through one of the conversationalists growing silent or politely moving on.
- Movement to another media of communication
- This stage involved a variety of different media, and it was not always solely dependent on attraction or interest. Many times it was simply more practical to move on to another form of communication, and this was often the primary reason for changing media forms. Communication through email is both laborious for long-term communication and impractical for getting to know someone in a personal way. Unless you can easily arrange via email to meet up in a safe public place, you will need to move to another form of communication in order to gain useful information about the person you are interested in.
- Meeting up or ending the conversation
- This last stage is the most nerve-racking and the most burdensome, but this is where you want to be if you really want to be in a personal and possibly romantic relationship. Although you can be hurt at any point, this is the stage where you are more likely to be hurt and more likely to actually learn more about yourself and the person you are interested in. If you are on an online dating site and are not reaching this stage, you may want to reconsider your motives and goals.
- A Note About Cat-fishing (Online Scammers)
I routinely encountered online scammers (probably about one per month), and I have a list of embarrassing messages from one individual who “cat-fished” me for about a week. As the story became more and more outrageous and the person finally asked for money, I realized that my online profile pictures and email correspondence could be used to craft another story designed to manipulate someone else. So, don’t correspond with people outside of the online dating platform, don’t send people pictures or information about you that you don’t want to share with the world, and don’t ever send anyone money. I made the first two mistakes (I corresponded via email and sent pictures that included people other than me), and I regret it. All of this is a good reminder to re-think one’s privacy, social media presence, and online footprint in general.
I poured a lot of effort into online dating over a period of 7-8 months. I filled out every section of my online profile, often using the maximum allowed word count and photos. I had template messages set up to save time when introducing myself or not introducing myself to people who I was interested in or who were interested in me. I always endeavored to be polite when ending conversations, but I ultimately offended a few people. I filtered through over 1000 profiles and sent or received over 250 messages. I met up in person with few individuals, and I encountered very few online profiles (probably less than 10 in total) of people who lived within a 2 hour drive from me. Ultimately, the people who I did meet up with required me to travel to different states to meet them, and those conversations were eventually ended due to the impractical nature of distance between us.
- The Mental and Emotional Struggle
To explain the complicated, emotional roller-coaster that online dating can be, a reflection that I penned during the experience follows:
“Online dating, thus far, has stressed me out a bit because I find myself willing to chat with people and get to know them, but I also find myself realizing that I need to be a little selfish and certainly realistic with my expectations and the expectations of those women I interact with. I can control and be responsible for my feelings, thoughts, and actions but I can’t do the same for others. I have to keep in mind that many women may not want to just chat it up online. Also, I have to say yes to one person eventually and no to all of the rest. I don’t want to reject a lot of people on my way to finding one person – that’s a lot of pain for a selfish reason, but I don’t want to give my future self a bad situation because I wasn’t intentional about choosing to be with someone who can increase my future well-being.
It’s nice to think we can always be friends. It’s nice to think we can find time to hang out, near or far. It’s nice to think that as long as we really care about each other’s well-being and needs that we can be happy with one another regardless of romance or physical intimacy. But, this is a very generous thought. Someone is likely to have expectations unmet. Someone is likely to be the one giving up more to maintain a friendship.
I suspect a lot of people on online dating sites are looking for commitment to an intimate, romantic relationship. That’s something that I want too, but if I could choose one thing to have in a long-term relationship or a short-term relationship, it would be friendship. In other words, I find it very difficult to commit to a long-term intimate, romantic relationship (because I take that type of relationship very seriously), but I find it natural to commit to friendships because I believe friendships are self-sustaining (the interests and past experiences of friends continually revitalize the relationship). Different factors (e.g. geographical distance) often place barriers in friendships, but the best friendships in my life are the ones that I can pick right back up with the commonplace sense of humor, interests, or activities that fuel the friendship. So, my expectation is friendship first, and commitment to an exclusive relationship is something that, for me, must come after long, careful consideration.
People are naturally selfish, and it’s difficult to feel and think that we have found a good match. There will always be something right about someone and something wrong about someone. Every person is beautiful in one way and ugly in another way. To not see both the beautiful and the ugly in a person, is to ignore their humanity through elevating them to a god or demoting them to an inanimate object. When I think about the practicality of a long-term intimate friendship, I think it makes sense to look for someone easy to love well and someone who finds it easy to love me well over a long period of time. The problem is that love is a choice more than a feeling and that love is, at its essence, characterized by self-sacrifice. Also, the multiplicity of factors and variables that contribute to long-term compatibility is staggering and seems impossible to accurately predict. So, the two intractable problems related to love seem to be compatibility (i.e. love as a natural feeling) and plain choice (i.e. love as a sacrificial action). Humanity seems to lack the intelligence to predict or create the former and the strength of character to produce the latter.”
- Things To Learn From Online Dating
- If you cannot or are not meeting up with people, it’s not personal and it’s not worth it…
- If your goal is a romantic relationship outside of the virtual world, do yourself a favor and safely meet up with people in public places or don’t waste your time.
- Be kind, and don’t be offended…
- You will stop talking to someone and you find people who will stop talking to you. Be as polite as you can be, and don’t get upset when people stop talking to you. It doesn’t necessarily mean they think you are a terrible person. If people are trying to make the best decisions for themselves, we cannot reasonably expect those decisions to be found easily. Try not to imagine that people are rejecting everything about you. It’s more likely that they didn’t like a few things, and those things were their “deal-breakers”. If you can figure out what those things are and if you want to change them, please do. Otherwise, be aware that the person who you are will be rejected by many, especially when it comes to romance, and unless you are apathetic toward a pattern of problems in you life that need to be addressed, that’s okay.
- There are a lot of amazing people out there…
- I met some amazing people living in other nations and cultures. I had great conversations about culture, work, and life. I tasted foods I had never tried before, and I was introduced to ideas I had never thought before. I considered what it may be like to be a responsible single parent – reflecting that it’s both difficult and that it’s a privilege that needs to be protected. I empathized with fears, desires, and experiences that I had not previously considered. I thought about what it may be like to live in other nations and/or on other continents as foreigners or nationals. I considered what it would be like to live life absent from some of the voluntary constrictions that I currently place on my life. I was introduced to some really intelligent people, adventurous people, and some really grounded people. And, If I got nothing else out of the experience, I can recall the individuals who introduced me to the ideas of circus and R-stats. I had conversations that helped me to understand that elevating cultural, biopsychosocial, and socioeconomic needs above the manufactured idea of race may help to soften the dangerous rhetoric and divides arising from people’s innate and developed prejudices. Of course, I took and left a lot of ideas I was exposed to. The point is that I was exposed to new people whose personalities, experiences, and ideas enriched my life.
- Go on some dates…
- When I was online dating I went on a few dates. While those dates were with some pretty cool people and while I experienced some new places along the way, it’s way easier for me to date people who live where I live.
- If you live in a rural area, you may want to try multiple online dating sites, be open to long-distance relationships, or not try online dating at all.
- While I thought the online dating would help my chances of finding a partner, I only signed up for one dating site and I went on a few dates as a result of my search. I drove or even flew to meet up with those people. If, like me, the small town and rural area that you live in decrease the sample size of your dating pool, and you have discovered that you are not good at nor have a desire for starting relationships over a long-distance, do yourself a favor and move or date locally.
- Study yourself (i.e. learn your strengths and weaknesses)…
- As my online dating experience progressed I began to realize that I have issues with trust and commitment, among other things. I already knew about my fear of failure and my analytical nature, but after my online dating experience, I better understand that my perception of the lack of commitment trending in my generation is something I am not immune to. I wanted a romantic relationship to be easier, and my embrace of online dating was likely fueled in-part by my own fears and lack of commitment. If you, like me, have a desire for a long-term, monogamous, and romantic relationship, you should gird yourself with practicality, patience, and courage as the journey is fraught with as much if not more risk and rebuke as reward. If you want love to be as easy as possible, focus on compatibility. If you want your love to involve devotion, self-sacrifice, and conscious choice, focus on practicing that love and finding someone who shares that conception. If you want a joyful long-term love that embraces compatibility and sacrificial love, focus on both compatibility and conscious choice (i.e. friendship, values, intentional practice, reconciliation, etc.).
- Note: One piece of advice that I have always found beneficial is to write out a “Top 10 List” for your “Top 10 List”. In other words, you should be able to find 10 characteristics that support or complement the 10 characteristics that you desire in a significant other, then you should practice those behaviors. I have also find it helpful to make the “Top 5” of that list most important and the “Top 3” of that list non-negotiable (for both you and your future partner).
There’s plenty of online dating advice freely available on the internet. Here and here are a few of my favorite Technology, Education and Design (i.e. TED) Talks addressing online dating. Also, Hannah Fry’s book, The Mathematics of Love, is an intelligent resource for dating in general.
If you don’t know how to create an algorithm to find your best potential mate or if you grow fatigued with the online dating journey, join the club. My intuition was that online dating was not for me. In 2018, I abandoned that intuition due to my feelings of loneliness and desperation to find a partner. Now, I’m embracing that old intuition once again. After 7-8 months of what often felt like online shopping for a romantic relationship, I quit the online dating scene. I have heard that it works out well for some, and I certainly learned a lot from the experience. So, if you are considering online dating, I encourage you to be careful with your expectations and vulnerability, heeding some of the above advice, as you give it a try.
Christian, B., & Griffiths, T. (2016). Algorithms to live by: What computers can teach us about
solving human problems. New York: Henry Holt and Company. Audiobook.
Fry, H. (2015). The mathematics of love: Patterns, proofs and the search for the ultimate
equation. New York: TED Books / Simon & Schuster.
Kang, A., & Kang, D. (2015, July 27). The Beautiful Truth About Online Dating. Retrieved July 4,
2019, from http://www.tedxucdavissf.com/talks/the-beautiful-truth-about-online-dating/
Manning, W., Smock, D., & Fettro, P. (2019). Cohabitation and Marital Expectations
Among Single Millennials in the U.S. Population Research and Policy Review, 38(3),
Martin, P., Astone, S., Marie, Peters, N., & Elizabeth, H. (2014, March 31). Fewer Marriages,
More Divergence: Marriage Projections for Millennials to Age 40. Retrieved July 1, 2019,
US Census Bureau. (2018, November 14). Historical Marital Status Tables. Retrieved July 1,
2019, from https://www.census.gov/data/tables/time-series/demo/families/marital.html
Webb, A. (2013, October 2). How I hacked online dating. Retrieved July 4, 2019, from