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Dating: A Newly Single Woman’s Guide

It is the moment of truth, I am finally addressing the world of dating when you are newly single! I talked about this my previous post and I have finally dove in and attempted to put together my little nuggets of wisdom. Hopefully, I can address all your unanswered questions. I know I had an idealistic view of dating, I thought I would have a summer fling filled with lake days, bike rides, hiking trips, and drive-in movies but its been more of a hot girl summer with nights out and day drinking at the beach. Since writing this post, I actually reflected and I have a new outlook on dating, a more optimistic view on embracing this changing landscape.

How Long Should You Wait Before Dating

I read that you should have a holding period of one to three months before you start considering dating. Which I think is a good rule of thumb. There are some people that suggest that you wait one month for every year that you dated your partner as well. It really depends on how you feel. I fully believe that you just have to listen to yourself. Everything I learned about dating I either read on the internet or was coached by my single girlfriends, bless their hearts.

Where to Start

So, what does dating look like after getting out of a serious long term relationship? It’s on an app and it is basically accuracy by volume. Its an endless string of casual drinks, coffee chats and walks around the seawall; It is not straightforward at all, with all the apps it is easier than ever to meet someone new, yet challenging to form a real connection.

I know I told my single girlfriends that I was just going to meet someone organically and they laughed in my face, I guess that’s not a thing in 2019. I want to tell all the women out there not to give up. It is totally possible to meet someone in real life, you just need to create more opportunities. Go to places alone, take to strangers, feel comfortable to do things on your own.

With that being said, it that seems daunting , here is the quick and dirty on dating, dating apps and how I have been trying to overcome my dating struggles. It’s a whole new world out there. I started my online dating journey a couple of months ago, so I am no an expert, but here is my experience and what I have learned so far.

There is an App for That

My first-ever dating app date, my date asked me what apps I was on, and I thought, wait a minute, should I be multiple ‘app’ing? I was overwhelmed by having just one app. I really just enjoy the swiping, but I hate the messaging back and forth and maintaining multiple conversations. Little did I know the endless supply of men runs out…so time for a second app…

Personally, I saw the same people on both apps, so it is completely unnecessary to have more than one app. The best word of advice I can give you is just to choose the right one for you. Deciding who you decide to move from chatting online with to meeting in real life is challenging enough so why have the added the effort of trying to keep up with multiple apps. I also learned that you never do dinner on a first meeting, cause if your date is a potato you are stuck to suffer through it. First meetings are reserved for casual walks, coffee chats, happy hour, and after-dinner drinks.

The Options Available

For a long time, I have actually been marketed to as a single person. Since my ex didn’t have Facebook, I don’t have a relationship status so Facebook targeted me as single. There are a million options out there, Inner Circle, Parrot, Happn, The League, but I decided to go for the most mainstream ones. I don’t need an elitist dating app, I can only imagine the type of candidates there.

Bumble: An app developed to shift the power from the men to the women.
How it works: both parties need to match and once they match, the woman has 24 hours to reach out to the men and make contact.

Hinge: In my opinion, this one has the best interface of all the apps, very interactive with fun conversation starters.
How it works: unlike Tinder both parties do not have to mutually agree to match, one party can send the other a heart and then decide if they want to initiate conversation.

Tinder: The OG in the dating world, now affectionately known as the hookup app. I know some of my girlfriends like it because it is in the men’s hands to make the first move.
How it works: both parties must swipe yes to match.

Is meeting a guy in real life easier?

Hard to say, no stranger on the street has taken the time to chat me up and ask me out, aside from drunken homeless men. I still pine over Bryan, a random guy my girlfriends and I chatted to on the way to the liquor store. one Friday night. Aside from that, I had two wild nights out at the bar, both resulted in the exchange of numbers. I went on dates with one and not the other. Neither were age-appropriate for me. Personally, I don’t like going to the bar so meeting someone there is probably not the best avenue for me. If you can I would suggest trying to pursue a new hobby and maybe meeting someone there or allow yourself to give in to being set up by your friends.

Time to Flirt

I am literally the worst flirt-er. It took me so much time to try and do anything that resembled flirting. If you are like me, enlist your friends, I literally would screenshot conversations and put it in a group chat and we would overengineer my replies so I am flirty and fun. I am getting better at it now, but it has been a process. I now text on my own, maybe not as successfully.

As someone who is not a texter in the first place, the messaging back and forth is so mundane for me. I actually got reamed out on quite a few occasions for delayed responses or lack of enthusiasm. I have finally warmed up to texting and as long as we aren’t stuck in a “how are you” or “what are you up to” type of routine I am good with it. Random questions or fun facts help.

Chemistry is Real and Hard to Come By

My newly single girlfriends and I were chatting and we were trying to decide how many dates to go on before we pull the plug and decide it’s just not going to work. We couldn’t decide if we were just not in the headspace to date or if we forgot how.

The answer, if the chemistry is there, you will know. I was trying to do the one or two date thing and see if things “heated up”, but instead things would start to fizzle. As someone who has a super short attention span to begin with, I found if I was kind of into it the first date, then by the second date I was tired of keeping the conversation alive and I definitely was not building a stronger connection or attraction to that person. Which brings me to my second point…

Lean into Authenticity

My early dates I tried really hard to make my date feel comfortable and fill any awkward silences but it ended up being a headache in the long run. I was giving my dates a false impression that things were going really well and then I would have to tell them after that I was just being nice and I don’t feel a romantic connection. I have now been coached on this and I allow it to be uncomfortable and get my date to do some of the heavy lifting. If things are uncomfortable, we don’t need to go on that second date.

I also found that being authentic and honest, helped my dates to be more authentic and honest with me to build an actual connection, even if it just was a friendship connection. I actually decided to pull some crazy out on one of my dates just to try and get it over with and instead of scaring him away, it actually prompted us to have a very real and nice conversation. Vulnerability is good way to build a stronger bond and actually connect with people.

Dating 101

One of my dates told me that he looked up the top ten conversations starters to use on a date just in case we had nothing to talk about. As someone who loves to be prepared, I loved the idea and I can’t believe I didn’t think of it first.

My recommendations, especially after being out of the game for so long is this:

  • Try to be in control for the first date and choose a place you are comfortable at or that is close to home.
  • I was barely invested in my first few dates, so if someone is out of a recent breakup, run away! Give them some time to figure out their sh*t, unless you want something strictly physical.
  • If you are meeting someone off of the app, do not commit to a dinner or a real date. It is way too much pressure. Sandwich it between other plans so that you have an exit strategy.
  • I break this rule, but this is the first thing my girlfriends told me; even, if you are stoked on someone, keep swiping. Everyone is dating/talking to other people until it is official. I can only concentrate on one person at a time and since there is an abundance of people on the apps, I this its easier to go back to the app once my current situation has fizzled out.
  • I have heard these are the dating rules, kissing is reserved for the second date and getting intimate is reserved for the fifth date. That being said, totally do what you are comfortable with, it was just good for me to know the general metric.
  • Don’t put too much effort into getting ready. I used to obsess over my outfits and then I would arrive and be like well this was fineeeeee. Avoid the let down by just not overthinking it and putting too much time into it.
  • Post date communication is confusing. I have been told never text a guy after your first date. According to my girlfriends, the guy should text you the next day and say, ” Hey I had a great time” or ghost you and never text you again…haha jk… In my experience that has been the case, so just play it cool and let him do some of the work. I also thought there was a multi-day rule for contact, but I guess times have changed, people are always on their phone, there is less of a holding period.

Know the Red Flags

The one thing I learned is that some people are not normal. Be very aware. If a guy sends you a shirtless picture, he probably just wants to hook up. If a guy you have never met gets sassy with you? He is probably not boyfriend material. If he is waiting until 5PM on Friday or worse 3AM on Saturday to make plans with you, you are probably not his first choice. All of the above will definitely happen to you. Guys are the worst, but us ladies already know this.

Be Respectful

It was a running joke within my friend group that it is not called Plenty of Friends because I literally would say after every date I went on that I would totally hang out with them as a friend. My single girlfriends had to tough love me and say that no one wants to be my friend. If you are on a dating app you are there to be more than friends, so shooting a couple of ‘bros’ in their direction and saying I like them as a friend is not going to fly.

There were a few guys that were super nice and there really wasn’t anything wrong with them at all, but they just weren’t the guy for me. I knew I wasn’t into it because when they text me I would just be annoyed or bored. I tried to create space, which made them only work harder, trying to make plans with me way in advance or entice me with more exciting or thoughtful dates, which a normal person should be stoked on. Instead of ghosting, I just simply told them for me the chemistry is not there. It actually went over well and I felt better not leading them on or being rude by just ignoring them. Be better than the riff-raff out there and just be honest.

Know That You Are Now a Target

Did you know that Instagram is actually the new dating app? Maybe not as obvious but when people find out you’re single the DMs tend to get a little more random and interesting. You also become the automatic target for anyone in your circle that has another single friend. Being set up is literally the worst, but there is no avoiding it. Know that now that you are single, every time you attend an event there is a high likelihood someone has brought someone to meet you. I have not found a workaround for this one yet, so if you have one let me know!

It Takes Time

I remember a dating app sent me a notification that said congratulations on your 91st match! My automatic reaction was, how have I matched with almost 100 people, met up with five guys, and not had one single good connection. These odds are terrible. What a waste of time.

The accessibility to other singles, while very liberating it is also super exhausting. My only advice is to be patient and try to have fun with it. After my second week of playing on the apps, I got way more agro, I would unmatch right away if I wasn’t feeling it, I started to ask for Instagram accounts to get a better insight (I was struggling to even understand what people looked like just based on the apps) and I was more careful with my time. I would never give a date a Friday or Saturday night. It is important not to let dating take over your life. If you do feel like you have fully recovered from your break up, it may be time to bite the bullet and opt something like eharmony where there is more of a vetting process.

Have a Buddy

Relying on my tribe for help is probably the best piece of advice I could give anyone. I haven’t dated for six years and even before that I was only single for a few months. My previous dating experience is very limited, all my significant others I met through mutual friends. Going out with a complete stranger is completely out of my comfort zone.

My girlfriends were great for being my wing women, coaching me through unchartered territory and keeping me sane. I don’t know what I would of done without them.

Have Fun, Its Personal but Its Not

Dating can feel like work, especially with the apps, so I think it is important to just have fun with it. My single girlfriend and I basically talk every Sunday night and share our dating stories, all the weird crazy irrational things that go through our heads, how we got ghosted and then unghosted, then submarined…I don’t know all the terminology. People literally have their phones on them all the time so if a guy isn’t getting in contact with you, it is simple, he is not worth your time and he is just not that into you.

Know Your Worth

Depending on how your relationship ended there can be some trauma there. I know in the past I had made excuses for my significant others and spent a lot of time protecting and defending them. I realized that that is a trigger for me. I think it is important to vocalize your triggers, be very transparent in what you are looking for and make sure you are on the same page as the people you are dating. Don’t be afraid to speak up and say what you need and if you aren’t getting it, be prepared to walk away. It is simple, if he likes you, he will do what he can not to lose you.

Get Out There

It seems simple, but I have had so many people come up to me and tell me how proud they are of me for getting out there post-breakup. It is really only daunting if you make it daunting. Once you take the plunge it just gets easier. I have no idea what I am doing. I tend to break all the rules, I bring up my ex, I go hot/cold, and I overthink literally everything. The important thing is that you try.

The Best Resources for Me

Hello, I am a loser and guess what I did, I researched how to date, how to flirt, what the milestones are. Hopefully, some of these links will help guide you through the dating journey. So here you go, here are my best resources and articles:

Sexy Confidence: I hate his handle but he does have some good dating advice. His videos basically address all situations that you will go through in the modern dating world.

Jake Woodard: Not so much dating help but great to help you heal post break up and a get a clearer idea of what you want out of dating.

Matthew Hussey: coaching and dating advice for women, a little bit sales-y but useful if you want to look up troubling topics.

How Often to See Each other When Dating: I lived with my partner and we mastered the mundane, Costco trips, folding laundry, dinners together, I had no idea what seeing someone new looks like, so it was helpful to know what the “norm is”. The answer once a week for the first month. Psychology Today is basically my resource for figuring out all my feels and tough life questions.

Love Languages Quiz: I think it is important to know what you value in a relationship so you can vocalize it early on.

I literally never thought I would be dating again, but now I am very aware that nothing is forever. I bought an outfit on sale for my ex’s annual Christmas Party months ago cause I like to plan ahead and now I barely know what I plan on having for dinner. It has given me a new insight to really put time and effort into my relationships and maintain them. I try to prioritize my friendships, have real conversations, and embrace the new freedom I have. I recommend doing some self-discovery before taking the plunge back into the dating world. Knowing what you want and what you are ready for can really make the difference when weeding through the pack.

Vancouver based lifestyle blogger. Visit my blog and discover travel guides, fashion tips and recipes.


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