Sex & The Chi-City: 5 Dating Tips to Improve Your Love Life

When did caring stop being cool? I’ve been dating for over 3 years. I’ve had 1 relationship and 1 dating situation and many, many, many first dates. I’ve rewatched every Sex & the City episode, in disbelief that a lot of the story lines are true and REAL. Many of us single ladies have gone through different scenarios. But back when Sex & the City was airing, I thought the characters’ situations were exaggerated, a script, but fast forward to 2020-2021. . . most of the shit is real and it’s gotten worse! Dating apps have created monsters out of both sexes and men have gotten worse over time. Effort, time, quality vs. quantity, caring vs. games, one vs. multiples, kindness, and manners have disappeared. So how do you actually find a real quality man?

Since I get quite a few DM’s I thought I would put together some advice I’ve learned along the way and some are based on frequently asked questions by you guys. Do not think I’m an expert, or claim to know it all, but I know that I’ve had some success in dating and working on myself to attract the right men.

Here are my top 5 dating tips to improve your love life (a lot was based on what you asked of me on my Instagram stories).

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{1} I am choosing and not waiting to be chosen. 

Enter a first date or most dates remembering that you need to make sure you like the other person NOT wondering if they like you is key. The focus is on whether this person is the right fit for you and really, why does it matter if they like you or not? It only matters after you decide YOU like them and they seem to be someone you may want to see again.

Whether or not someone likes you, does not and should not affect how you love yourself. Not everyone is going to like you. Not everyone likes me and that’s ok! I don’t love everyone and it doesn’t mean that person is a bad person, just means the chemistry wasn’t right. Once you lean into this thought process you’ll stop worrying about what others think and focus on yourself. That confidence shows and attracts others.

I get my feelings hurt only after I have put my energy into someone. I guess in my work online I have thicker skin, but strangers are always going to have opinions, people don’t REALLY know you, so their opinion doesn’t matter. How many times have you made a judgment call on someone without really knowing them? It is those that we spend time with, close friends, family, relationships that make the biggest impact and that should matter. So until you really get to know someone, don’t wait to be chosen. Choose to listen, see actions, and feel the chemistry and you choose if your date is worth moving forward with. If they don’t ask you out again, that’s ok, they weren’t meant to be chosen by you.

Regarding any ex situations, I love this statement. If they chose someone to get over you and you chose yourself, you are WINNING. Know the difference.

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{2} Dating starts and ends with you. Being complete begins with you, not finding someone.

When I first started dating after my breakup I was a mess, no one could tell as I am fine on the outside, but inside I was not emotionally set to find someone to be in a relationship with. I went out on a lot of dates and many times, the guys I attracted were a mess themselves. With spending more time alone, writing a journal, looking at affirmations and what I want out of life, I’ve accomplished a sense of happiness and peace that’s wonderful.  The past year or more, I’ve attracted better quality men and find myself even friends with a few guys I was seeing. I always recommend working on being happy inside, when that happens, things unfold. My perspective about life, job, dating has changed and I’m having fun doing it.

Despite dating challenges, I’m very happy. And even through small dating relationships, I know my worth and if something doesn’t work out, I can simply walk away looking at what I learned from it and what I would do differently next time.

NO ONE SHOULD COMPLETE YOU, they should add to your life, not be your life.

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{3} Stop playing games.

If you want to text, text, if you want to call, call, if you are looking for a partner or relationship just be yourself. If someone doesn’t love you for who you are it isn’t right. Toxic behavior attracts toxic people. I know there are a gazillion books on how to play the game, how to find a partner, “why men love bitches”, etc. but the main things I have found is to evaluate your behaviors, why are the same things happening, and change that narrative. Make decisions to evaluate the process rather than playing games. The thing is, when you are living your best life, you stop waiting for calls, texts, and when men or dates happen, they feel good, not desperately needed. I can’t reiterate enough, but when you know your worth, your decision-making changes. If someone isn’t interested, you move on. You don’t call or text incessantly, you make different decisions. During breakups, you don’t say, “You’ll regret this”, you say, I am worth more than this and move on. When a guy stops messaging, that person wasn’t meant to be. Don’t give someone your energy that doesn’t see how amazing you are.

I know it isn’t that simple, but the mindset is everything. In my last two relationships, the guys texted back immediately when receiving my messages and vice versa. This whole waiting hours to communicate back rule is ridiculous. Just treat each other like people. COMMUNICATE WHAT YOU LIKE OR DISLIKE instead of playing games. This has helped me move forward or break up with people. Sometimes after open communication, both people realize they aren’t the right fit. This helps eliminate seeing someone who isn’t right for you for too long.

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{3} Breakup/dating mentality: I would rather adjust my life to your absence than adjust my boundaries to your disrespect.

I heard this on tik tok (yes, this damn app has changed my life) and it’s one of the best things I’ve ever heard. I’ve been sharing it with my friends and to me, it was a lightbulb moment. It’s so true. and I don’t even need to write much more. Knowing your worth is gold and to walk away from bad situations sooner than later is much needed.

{4} Know your intentions in dating.

This was one I learned as of late. I started dating without any intentions. When people asked me what I was looking for, I said I was dating but wasn’t sure. Because of my unclear intentions, a lot of my dates were “fun” and the men perceived me as “fun”. As I made mistakes along the way and figured myself out, I realized I did want a partner and started dating with intentions and communicating that I was looking for a relationship. It took me a while to get there but it definitely helped me attract those looking for the same things. So when people ask now, I have clear intentions and there are no mixed signals.

If you are looking for marriage, I do think it’s best to start by saying you are looking for the right person to have a relationship with. It’s safe to say, jumping the gun to “marriage” and “kid” talk scares both sexes. It has scared me before. So when I say intentions, I would say figure out if you are dating for fun or seriously.

I feel like this piece of advice was important for me but many of you know you are looking for a partner. After divorce, I was very confused on whether or not I could commit again or if I wanted to get married again. It took me years to figure out my intentions and love is hard. So take your time and enjoy the fun if you can and figure out what you are looking for.

{5} Stop “hanging out” and have some guidelines on what is acceptable for you in dating.

I personally HATE when men ask to hang out. I’m not in college and I could hang out with my friends. These are general guidelines I use and you can take it or leave it but I do believe that the level of effort in dating translates into the relationship and marriage.

  • If you are app dating, I pretty much require anyone who asks me out to do a facetime. It wastes less time and I can tell if we have chemistry or good communication after the first call.
  • Don’t waste longer than 1 week chatting on an app. A real man interested in dating will ask you out within the first few days. If they don’t, move on. You don’t need a penpal
  • If you aren’t sure about chemistry after the facetime, do coffee/lunch or drinks.
  • Dinners are for those that you are interested in and see the potential. Believe me, having dinner with someone you don’t like is PAINFUL.
  • Limit drinks on a first date to 2-3.  (I’m the worst at this, but when I have, I definitely have a clearer picture lol.) I love to go out so sometimes it ends up being more as I’m way too much fun.
  • I don’t have anyone pick me up or drop me off due to privacy. Until I know someone, I don’t want them to know where I live.
  • Notice if they hold the door open, walk beside you or in front of you, walk on the side of the street where cars are, if they are nice to wait staff, look you in the eye when speaking, ask questions about you. Manners are everything.
  • So if someone you like isn’t choosing dinner places or h0lding the doors open etc. I think it’s ok to mention it kindly to them that you like those things. I’m not so black and white that you break up with everyone that doesn’t meet expectations, I believe in communication and after you do tell them, do they make those efforts? My past mistakes were breaking up with everyone if something small got in the way. I now realize if I have chemistry I communicate my needs and if changes are made, I greatly appreciate it.
  • STOP HANGING OUT AS DATES this isn’t dating. I guess it is ok to hang out if you’ve established you are dating each other or you just don’t care about going out and you both want the same things. But beware, marriage or long term with this person will always be this way.

Don’t accept the bare minimum! If we all expected more, men would change their habits. I’ve asked men before if they would treat their mom, sister, or daughter the way I was treated and it brought forth very strong reactions. Men need to treat women, even strange women with the same respect their mom or sister deserves. PERIOD.

What I’ve heard from guys that are good at dating. Women are so grateful when they make dinner plans or offer to pick them up or do the bare minimum items like showing up. WOMEN! You can say thank you but not so over the top thankful that a man thinks they are KING. Literally doing common things like pick a place for dinner, walk you to a car or call you is not that amazing. This is literally the bare minimum and even my high school boyfriend did these things! Come on, let’s expect a little more. Appreciation yes, but thinking they are the one and special is another. These guys have said many of their first dates turned into the girl literally almost moving in as they were so happy to found someone that DID something.

You can still choose happiness even if it looks different than your expectations. Having a boyfriend, partner or husband does not mean happiness. Dating is super hard, but attracting the right people really does begin within yourself. When the wrong men appear or if one enters your life, you can make the right decisions that they aren’t for you and end it sooner than later.

I have quite a bit of dating stories from you ladies and since this post was longer I will share on another! I did another dating tips post last October and I hope all these tips help (scroll down). I do not at all think I’m an expert – I just love sharing what I’ve learned in hopes it will help any of you.

Still my favorite quote from a previous post.

Jennifer worman, red soles and red wine, chicago blogger,there will be a man that deserves you quote, dating after divorce, finding love after divorce, dating advice, top dating questions, dating during quarantine, chicago dating, dating life,  dating series, dating blog, top questions about dating, real life dating stories, real talk, dating quotes, finding the one quotes, know your worth quotes, don't chase men quote, dating quote, finding love quote, dating after divorce quotes, single mom dating quotes, real life quotes, real talk


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