Sex & The Chi-City: 10 Things Women Expect on a First Date

Jennifer worman, red soles and red wine, chicago blogger, sex and the chi-city, dating series, dating advice, what women expect on a first date, first date stories, chicago dating, dating life, dating after divorce, dating series, dating blog, what to expect on a first date, 10 things women expect on a first date

Single ladies, we all have expectations from the first date on. Let’s get real, for the 1 person that said expect no expectations, that’s just not feasible. To find the right partner, you need to have at least some core expectations of what you need in a future partner.  So here is a simple list of things you should pass onto your brother, friend, boyfriend, partner, hell anyone dating.  All those men who claim to be “trying to find a relationship”.  These aren’t difficult to do, but may land you more dates and hopefully a long term relationship. And for women, let’s stand up for ourselves and stick to these expectations before settling. Yes, the hurry to marry is there if you feel lonely, are told your eggs are dying, that you are too old to be single, or that two people means you are complete. I started a post recently (which I never finished) about how people kept saying to me, “You’ll find someone, don’t worry.” “This special someone is out there for you.” But I’m not worried? I don’t think to have someone else completes me. And I especially don’t think to fill that space means I’m now better.

Believe me, having the right boyfriend/husband is so much better than a man that isn’t right for me and I’m unhappy with.  Currently, I know so many people unhappy in their marriage which in turns makes them an unhappy person.  So remember this single ladies, getting married does not equal completion or happiness.  You must be happy with yourself in order to find the right partner for marriage.

So here goes, and stay tuned for some funny stories . . . and this series won’t be about just my stories, it will be about readers stories as well and you won’t know if it’s mine or someone else’s :).

Jennifer worman, red soles and red wine, chicago blogger, sex and the chi-city, dating series, dating advice, what women expect on a first date, first date stories, chicago dating, dating life, dating after divorce, dating series, dating blog, what to expect on a first date, 10 things women expect on a first date

{1} Respect

So this was the number one item on my poll! And this leads to both sides. As with my first topic last week (of this series: Younger Men), texts about being a sugar daddy or mama or asking for naked photos is not respectful and not needed “if” you are looking for a relationship or to date.

In person, be kind, be complimentary, and don’t put someone down. Don’t drink too much (lol sometimes I don’t take my own advice) and don’t touch or kiss when it’s obvious the person isn’t interested.  Read body language and “listen”.

Every date and relationship should have this and starting off the first date without this leads to a disaster.

{2} Men should pay for the first date, old school charms welcome

There was an overwhelming response that men should pay for the first date. I’m a believer of this but I also know it is now complicated. I’m sure there are women out there that want to split it, but to me, the first date is a simple gesture of “dating”. I’m traditional, I want the man to ask me out (although I have done bumble and have made the effort to have conversations first) and I want the man to pay for the first date. If a man, can’t or won’t do this then down the line it will just get worse.

Simply, if dinner is too big of a commitment, a few drinks or coffee is easy to do. After the first date, either can pay or you’ll figure it out.  It isn’t the money but the effort and men, ladies talk about effort all the time. From dating to marriage, effort and feeling like your man makes the effort, makes us feel good. Call us crazy, but we are emotional beings that want to “feel” things.

A friend told me that one time she met a guy at a bar and they had drinks together. At the end of the night, she said goodbye although he was trying to get her home with him. Both exchanged numbers and the next day he texted her that she owed him “$20” as he felt like the drinks weren’t worth it as she didn’t go back home with him and asked her to venmo him. WHAT? THAT’S NOT OK.

Another friend was asked out for a lunch date. She went near his office (as he picked the place) to make it convenient from him. During the lunch, the conversation was filled talks about his ex and judgments he made about her. When the bill came, he just stared at the check, she offered to pay and he took her up on it. She called her uber and jetted out. A few days he texted to her to ask her to hang out again.

Guys – don’t be cheap and also don’t play games of texting a few days later.

Other tips that women love:

If you like a girl, call her an uber home and make sure she got home ok. If she doesn’t feel comfortable giving out her address, make the step to text her to check that she got home safe.

Hold the door open (cars, restaurants)

The list could be longer, but the above are really easy to do for a first date and to show interest.

{3} On time

For ladies and men, be on time. Over 50% of my dates are late. Under 10 minutes, all ok. Over 30 minutes, not OK. Be respectful of the time and first impressions. If you aren’t going to show up at all, send a note/text/call and don’t be an ass and not show up at all.

{4} Ask Questions! Engaging conversation

How many of us have been on that date where they only talked about themselves? All of us have raised our hands. The best part of dating is getting to know each other so actually get to know the other person. Walk away knowing at least 5 facts about the other person or make it a goal. Be aware of self-talk and listening skills.

True story: I love learning about people and am pretty inquisitive. On a first date, I ONLY wanted to do drinks. He had other plans and we ended up dining together. In the 3-hour time span, I learned that he was divorced, loved strip clubs, and cheated on his wife with a stripper. At the end of the date, I was running home. He never checked that I got home ok, but did text me three days later to ask me out again. I told him the truth (as I hate ghosting), that I wasn’t comfortable with what he told me and I wasn’t interested. I’m not sure if he wasn’t reading signals, but I didn’t share too much about myself and learned a whole lot about him lol.

{5} Dress appropriately

First impressions are everything. I’m not going to lie that I like my man to look nice as I like to look nice. Don’t wear flip flops and look homeless on a date with me. If you love that look, then it’s appropriate. But read the person and place and make the effort. I haven’t had any big issues with this. I think based on how I dress it is obvious I’ll be dressed up.

{6} Have suggestions for time and place (extra effort)

So I love when a man asks if you want him to pick. So then you can say yes or no. I like when they take charge or give me 3-5 choices and we work from there. It shows some effort and that they want to take me out. What I hate is them asking what you want to do and then lazily say, wherever you want. Then an hour before the date, it’s still undecided and then I have to choose. This isn’t just me, it’s most of us that want to feel like YOU actually want to date and put effort into it.

Over ten years ago, I demanded every date be chosen by a man and every man I did date, called and made sure I knew where to go and picked me up from my place. They also dropped me off like a gentleman and asked me out on a second date.

Well, the dating app age has changed all of that. Which is ok, we know it’s a numbers game, but for a first date, selecting a great drink place really isn’t that hard. Effort equals interest in dating. Lack of effort is just a waste of time.

{7} Not be judgemental

This is in here as we all make judgments of each other.  Be open, be honest, and it’s ok to not like each other on a first date. Be ok knowing that not everyone is for you and vice versa. Go into each date with an open heart.

In my experience, my job makes it difficult to date. We might have a great date, but then they find my blog and Instagram and instead of getting to know me, they watch my stories and assume and make judgments on my life. I’ve been OK with it now, I want a man that sees past it and is confident and excited about what I do. I try to enter every situation being as open as possible. What you see isn’t always what you get and sometimes, the best people are ones you have to get to know!

{8} Don’t jump to inviting someone back to your place.

I’ve experienced this and hear this from other single ladies, the push to go back to their place after a first date. Don’t get me wrong, whatever your intentions are, you do you. We all go through phases of fun vs relationship dating. I think it’s doing your homework on the date, listening, asking questions, getting to know each other, etc. I’m sure some dates end at a “place”, but if it’s a great first date, there’s no need to rush it.  I wish more asked for a second date vs going back to their home.

Personally, when I first started dating again, I was shocked that 100% of my dates did this. I’ve learned so much since then and also know what I’m looking for so I’m clear on a date.

{9} Things will be awkward.

It’s ok to be awkward! The first time meeting will always have slight awkwardness. Whether or not you’ve met in person or online, it’s always nerve-wracking and both of you are trying to figure it out. Dating is a weird mix of chemistry, communication, and lifestyle . . . feeling awkward is perfectly normal and ok to feel.

{10} Chemistry

If there are chemistry and physical touch, a kiss is ok. If there is none, do not accost her face. Most people hope to have chemistry right?

I’ve been on several dates where I felt ZERO chemistry or wasn’t interested and experienced them zeroing on my face. I didn’t like it and backed away or went home immediately after the encounter.  Feel it out and as I said listen and look for cues. But if she isn’t going in for a hug or has indicated she is even interested with forward facing conversation, don’t assume because you feel something she does too.  Best bet yet, go in for a hug and look at her.  If she looks away, she isn’t interested, if she looks straight at you then go for it!

I think dating is best if you don’t worry if the other person likes you, worry if you like him. Make sure you like what he is like, how he communicates, and the chemistry works. Less stress on whether or not they like you, as the right person will. If he doesn’t, it’s ok, move on, wasn’t meant to be. As I get older, I care less about what other’s think and more about what makes me happy. Sounds selfish, but being happy with myself, creates better relationships all around.

Anything I missed above? And men, don’t be afraid to ask someone on a second date at the end of the date! It’s cute and much loved effort.




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