Dating Tips for the Online World

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By UB’s Michael Maloney, LCPC

I once had a client who stated that “Ok I’m okay with being single, but you know dating is the worst!”  Many of us feel that way and people often will go on online dating apps for a while and then feel burdened by the process that they will take a break from it.  Others try to go to events to find someone but keep having issues finding someone to ask out for some one-on-one time.

The truth is dating is an awkward process and no one is truly great at it.  For many whom go on dates, they find themselves self conscious about many different things.  They might not feel great about their bodies, or how they dressed. They might feel that they are boring the other person.  One of the biggest issues when people are first starting dating is “what do we talk about?” This last question brings up a lot of anxieties for people.  

Expectations of dating is something that you should pay attention to.  Some people hype up a date before it actually happens. It is very understandable.  Could this person be the one? How should I impress them? What if they want to have sex before I’m ready?  What if they don’t want to move as fast/slow as I want to? This of course puts a lot of pressure on the date in itself.  

Dating, as most of us see it, is a getting to know you process. It is learning more about who the other person is and them learning about you.  It is also a process of learning more about yourself and what you need in an ongoing relationship. What is most important is that you are clear with what you want, and not conforming your needs to fit what the other person wants.  

What is helpful with dating, in general, is know what you want.  We have to be honest with ourselves in what we want. It is often helpful that when we do understand what we want that we need to put it out there.  So if you aren’t interested in hookups – put that out there. Many people will put on their online profiles that they are not looking to meet up just for sex or that they are waiting until marriage to have sex.  If you are in social location you can also be clear what you are interested and/or not interested in doing. Being clear on your boundaries and interests is a great skill in relationships, both in dating and in life.  Sometimes it is uncomfortable, but it is often help to put your intentions out there.

Amy Webb, a tech journalist, created something that she called her Mary Poppins list.  In the movie Mary Poppins, two children write a list of all the positive traits they would like their new nanny to have.  Using this idea, Webb created a list of traits that she would like her partner to have. For Webb she saw it as a way to optimize her dating experience but it can be helpful in other avenues as well.  The nerdy Webb included on her list: Must be 20 pounds more than me at all times, Appreciates the beauty of a well-crafted spreadsheet, Wants to have two kids with me, Jew-ish, and non-smoker.  In all Webb had 72 “data points” in what she wanted in a partner.

Webb then broke her list down into different priorities.  Some of her data points were deal breakers in what she wanted in a relationship.  She wanted someone who shared her cultural religion and having 2 kids was non-negotiable to her; Those items went to the top tier of her Mary Poppins List.  Other items might also be important and they went on a second tier (i.e., appreciate a good spreadsheet) and others would be nice but she didn’t need (non-smoker).  Sitting down and looking at what she wanted in a relationship helped her refocus her dating habits.

Often when we are going on dates we are worried on how we are presenting.  This can be good as we want to try and impress the other person and not insult someone we are just meeting.   But it is missing the other half of the process. Dating is like a job interview: it is very easy to forget that you are interviewing the other person as much as they are interviewing you.  On a job interview you want to be impressed and want to work for a company while also wanting to impress the potential employer to want to hire you. That being said, Webb’s Mary Poppin’s list is a great way to build questions to ask your date.  

A good exercise is to build your own Mary Poppins list and understand what is important to you.   

How to build your own Mary Poppin List:

The first step is the brainstorming process.  Brainstorming is coming up with as many ideas as possible.  Webb came up with 72 items, you may have less or more but allow any idea to come up and write it down.  Think about the values you have and the type of relationship you want to build. What are the qualities about yourself you want to be appreciated?  What are ways a partner can take care of you? Think back about past dates or relationships and what were things that worked and didn’t work in those relationships?  Take some time and let any idea come out.

The next step is to edit your list.  Some of the ideas might be very similar to each other and it might be good to find common themes in your list.  Common themes might include someone who family oriented, have similar ethics as you, or enjoys certain activities as you.  

The next step is to look at what is the most important.  Find the things on your list that are deal breakers for you.  These go into your top hierarchy. I recommended no more than 5-6 at maximum.  You are trying to build your priorities, and if everything is a priority, than nothing is.  Next build a second tier list of 5-6 things that are very important for you. In your third tier is everything else but it would still be helpful to rank the items in how important they are for you.  Webb gave numeric values to each of her items to show how much weight she have each of the traits.

Now that you have your list now what?  You can use it in two ways. Webb found it helpful to see if people put information on their online profiles that matched closer to her list.  If you see something on someone’s profile that is a deal breaker for you, you can chose not to date them. You might also ask someone out who appears to have similar want or values as well.  Typically most apps accentuate the physical traits and pictures or a potential partner. While we want to make sure we are attracted to our partners, we also want to make sure we can connect with them in other areas as well.  

Once you are on a date the goal should be to get the information to see if this person meets your needs.  How can you get the information to see if this person gets a box checked off on your Mary Poppins list? Try figuring out questions you might want to ask.   I usually recommend asking open-ended questions (not something than can be answered yes or no). So if you would like to have kids you can ask “Do you want to have kids?” which only gives you a little information.  This style of asking the question might actually make the other person try and guess what the right answer as they might also be self-conscious on the date as well. Instead an open-ended version of this question might be “Tell me what your views of having kids are?”  This open-ended approach creates a conversation where the two of you can share your values and hopes for the future.

Webb, in her book Data: a Love Story, points out that on dating websites we often rely on the algorithms the apps give us.  But these algorithms are not designed specifically for us. They might help direct us to the right direction, but we have to learn to build it ourselves.  

Lastly initiating conversation for many people on apps or in-person, can often be awkward.  Think about what information you would need to know about the person before going out on a date.  How should you start the conversation? A simple questions to ask is how would you want someone to start a conversation with you?  Also what conversation starters would you want someone to ask you? Conversation starters are things you can talk about that feel safe and comfortable, but still engage a conversation.  Looking at a person’s profile and asking them to share something about themselves (using open-ended questions) often helps.

Also think about what medium of communication works best for you.  We have multiple ways of communication now, talking in person, on the phone, texting, messaging apps like Whatapps, dating apps, and so on.  If you prefer one over the other, be honest about that.

Again dating is awkward and not always easy.  But the purpose of these exercises is to turn in before the date so you can get to know the other person when you are on the the date and not worry about all the other things.  Once you know more of what you want, it might help you be more present in the moment and get to know the other person.