Back in the Dating Saddle

In a past post, I shared the details of how my last relationship ended about a month ago…days before my 30th birthday. In the last month, I’ve had a whirlwind of emotions go through me – for the first couple weeks, it was mainly sadness, confusion, and grief. While we were only together for a few months, she had become a big part of my life and I saw that only growing. I had been invited to her family’s events a week before I had “the bomb” dropped on me so she wasn’t exactly cutting me out of her life slowly.

This grief and sadness then turned to anger. How could someone who supposedly cared about me do this? I completely understand that you need to be true to your feelings and don’t fault her for that. However, what I do have a problem with is how I was treated in the aftermath, but that’s a whole other story in itself.

Now, I’ve moved on and am back in the saddle and ready to move on. I have 2 dates on the agenda for this week. So, with that being the case, the whole first date etiquette is on my mind so I wanted to take a look at it:

Where to Meet Up? Such a simple thing, yet so important. Where are we going to meet? My go-to is a restaurant with a bar…let’s be honest, nothing to kill the first date jitters like a little booze!

Who Pays? This is not even a question in my eyes…the guy does. Why? Because that is the rule. I honestly think it’s stupid and archaic, but because society says that “gentleman” will pay on the first date, I don’t dare touch this social norm.

Goodnight Kiss? This is such a polarizing topic – it makes the topics of universal healthcare, immigration, and marijuana legalization seem innocuous. I’ve had many debates with friends about what to do at the end of a date – kiss or not? Some of my friends are adamant that you got to kiss the girl, otherwise you are entering the “friend zone.”

However, I don’t subscribe to this school of thought. It seems a bit weird to me kissing someone that you met a few hours ago. I tend to go in for the kiss on the 2nd date – I mean, those extra 2 hours really make a difference right? But in all seriousness, this gives us both time to digest everything and inevitably find out whether there is interest or not on the other end.

When to Contact Next (and who should) if you want to go out again? We’ve all heard of the 3 day rule. “You have to wait 3 days or she will feel you’re too eager – you got to play hard to get.” This is another one that I personally don’t subscribe to. Maybe it’s because I’m impatient, but I’m usually texting the girl that same night saying I had a great time. I won’t life, a girl gets major brownie points when I pull my phone out to send this, and she has beat me to the punch. In those cases, I know that she is considerate, appreciative, and of the most importance, interested. I feel that you have to go with your feelings on this one– some people will wait, some people, like me, want to reach out right away.

What to do if you don’t want to see the other person again? Inevitably, most dates will end with at least one person not feeling it – it’s the nature of the beast. However, I still ask myself every time I’m the one who is not feeling it,“what should I do?” And, every time I do the same thing, fall off the face of the earth and not contact her. I’m not proud of this but what is the better alternative? Sending a text message that says “Great meeting up with you but I’m not feeling it” would be just weird. Of course, if the girl ever contacts me and gives the impression she wants to go out again, I’ll say “thanks but no thanks”….in a much nicer fashion.

So, give me your thoughts on these items – what am I doing right? What should I change up?



15 thoughts on “Back in the Dating Saddle

  1. On the subject of who pays, I like the idea of the gentleman paying for the first date, but my general rule of thumb is whoever asks for the date or suggests a meetup pays. If it feels weird letting her pay, then offer to cover the tip, a night cap, or even ice cream!

    I think a kiss on the first date should only be determined in the moment. Hell, I kissed my fiance before we even went out on a proper date and even then, I took him to a drive-up Sonic and ordered a box of tater tots (and I paid). A first kiss shouldn’t be rushed or happen because someone else thinks it should. First kisses only happen once (per person), so make it a good memory, always.

    And lastly, screw the ‘wait three days before contacting.’ We are living in an age of impatience. If your date, even for a second, feels like she is unwanted, she can have another date lined up with the swipe of her finger. This isn’t the 50s where our only source of contact was the turn dial phone and/or snail mail. If you enjoyed your date, tell her so!

    Liked by 1 person

  2. It’s always super fantastic when the dating horse 🐴 is waiting at the gate, and you are again ready to jump back on. However, isn’t holding onto the reins too tightly unnerving for the horse? Give yourself and the horse a bit of freedom to stray from the beaten path a bit more. Allow both of your hearts to race as you experience some unpredictability. Go off-script just a tad. And definitely have a giddity-up fun time. The moment you’re in, is the only moment that matters!


  3. I don’t know if it’s a regional thing or my modern attitude, but I always offer to split the tab. If the guy insists on paying, I’ll allow it and thank him profusely. However, 90% of the time he doesn’t insist so we end up going dutch.

    Liked by 1 person

  4. Reblogged this on Belle Papillon 24/7 and commented:
    Great post!
    Really refreshing… good to know these things from a guy’s standpoint.
    I have recently started dating and Seth makes some of the guys I dated look like douche bags. LOL

    No, chivalry isn’t dead.
    There are still nice guys out there.
    Don’t lose hope.
    Have fun! Life is short…

    Carpe diem!


  5. Call me old-fashioned but I still think a guy should pay for the first date.
    I always offer to pay for my meal or at least the tip or I invite them for coffee or drinks after the lunch/dinner if they insisted on paying for it.
    Bottom line, I’ll pay if they say yes but I won’t go for a second date if they’re that cheap to begin with. It’s a big turn off. If you think about it, the first date is both your chance to impress the other so if the guy decides to blow it by letting you pay then it means he wasn’t really trying to impress you and is not that into you so why bother giving this person a chance? Don’t think that this guy will always make a woman pay, he’ll probably even spoonfeed the woman if he really liked her.

    Kissing… I don’t believe in kissing on the first date — maybe coz I’m a little germophobe. LoL But seriously, the mouth is the dirtiest part of the body. However, I guess if you really vibed, hey! XoX

    Meet up place… restaurant if you’re really interested in the person. Coffee if you like it to be short and sweet and make her think you might be cheap. Seriously! But I like activities. walking by the beach, hiking or miniature golf is really cool!

    I don’t know about the 3-day rule. Too much mind game there.
    I like what Seth says. It’s really cool if a guy or girl says “Thanks for a lovely evening!” or something to that effect. It’s a great wrap up. It shows you’re interested. SOmething to look forward to and you know the other person had enough time to think on the way home that they want a follow-up date that’s why they’re sending this message (right?). Why make the other person wait 3 days and worry if you guys vibed or not? It’s torture. Please! Life is short. Enough of that nonsense. LoL

    Honesty is best. Please don’t ghost or fade out… and definitely, don’t resort to breadcrumbing. There’s no easy way but you can always practice tact. Just think if you’re on the receiving end. You can make excuses why you can’t see each other and I’m sure the other person will get it. And if they don’t, you’ll just have to break it.


    • I like the route you take for paying on a first date….I’ve gone out with girls and offered to pay for dinner and their response was I could on the condition that they pay for ice cream after or drinks after or pay for the 2nd date. These are the responses that win me over more than anything….A) she is showing appreciation B) she is showing that she has interest and C) who doesn’t love ice cream or drinks after dinner 🙂

      Liked by 1 person

  6. “This grief and sadness then turned to anger. How could someone who supposedly cared about me do this? I completely understand that you need to be true to your feelings and don’t fault her for that.”

    I’m not sure there is a right way to break up. I’m sorry for your feelings but I am wondering how she could have done things differently.

    I ended a serious relationship recently and I did it first over email and then we hashed it out in person. I did that in a public place because I did not want to be forced or emotionally coerced into ‘breakup sex’ (I was right, and he wanted to get together for one last time!).

    By the time I had digested ending things with him I’d already been thinking about the relationship not feeling right for a while, and had been circling around the suspicion that we’d run our course. Personally, I don’t think I could have done it any other way and I was kind, compassionate and careful not to blame him or upset him too much.

    Afterwards he wrote me several long text messages and emails of sadness and regret. I did respond with a fair dose of my truth and that helped me to have said it, but I don’t know whether it helped him to grow and accept his failings.

    We parted finally with grace, after trying to coax me back into his life one last time. By that stage I felt nothing for him except mild revulsion and anger at the way he’d treated me all through the relationship, that I’d never called out and had just accepted because I was so new to dating after a long-term marriage, and he was so much younger than I, and I felt like he didn’t know any better.

    I guess the lesson I learned was that if you bite down your feelings they will surface at some point. In your case, think on how she could have done a better job of ending it and what you would have liked to hear. Sometimes there is nothing to say except ‘this is not working’. Apologies for my long rant 😉


    • Thank you for sharing these thoughts. You’re right, I don’t know what could have been done differently….inevitably, most relationships/long term dating is going to end with one person feeling hurt. I guess in this case, I felt blindsided a bit. A week earlier, we were talking about how we were both in it for the long haul (granted, it was after a disagreement so maybe that was a sign). I’ve been on the other side before and had to end things because I didn’t feel it was right and it’s incredibly difficult, so I understand that we each have to go about it in our own way.

      I also think some of the anger I felt was towards myself….Why couldn’t I make this work? What was wrong with me?…..Did I do anything wrong? No (besides normal missteps that happen day-to-day). However, when you have something good that goes away, I feel it’s only normal to look to yourself and say, “what could I have done differently?”

      Your breakup sounds awfully familiar to a past one I had – incredibly tough to put it mildly. I guess the moral of both of our posts is that that there is no cookie cutter for this – there is going to be pain and challenges any way you go.


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