Things were really going well with me and “Todd.” He wasn’t necessarily my type in the looks department. He had an odd-shaped head. And call me silly but you know how some people have thick looking teeth. You know those teeth that look like they are too big for a person’s mouth. But he was tall, had great hair, and he seemed like he had his shit together. He was 46 but looked like he was in his late 30’s. He went to an HBCU which was always a plus especially in LA. He was originally from the east coast, which was a super-duper plus. He was in Pharmaceutical Sales and we met through a mutual friend. I really wasn’t interested in him at first because something about him just didn’t do it for me. I couldn’t put my finger on it. But I wanted to do things differently and give the guy a chance. At first he suggested meeting for lunch. I nipped that shit in the bud. I don’t do first date mid-week lunches. First of all during the day I am still in work mode and can’t switch it off easily. Lunch dates are reserved for men that I have had several dates with already. So he suggested meeting at the Firefly for drinks. That is always a great first date. If you realize that you have nothing in common with a guy you don’t have to sit through a full meal or text one of your girlfriends to call you with the “fake” emergency call. When I arrived I could tell he was a little nervous. I found that attractive. There is something so cute when you can tell a guy is really attracted to you. The conversation flowed. We talked a lot about the east coast. Come to find out although he had a full-time job he was an actor. YUCK!!!! Being in LA you meet so many out of work actors. And my first thought was, really? You’re damn near fifty, if it hasn’t happened for you; it’s not going to happen. However, I gave him the exception because he was pursuing acting in addition to having a full-time 9-5. I could respect that because at least he was getting a pay check. And understood the concept “In addition to…” He had a daughter in her early 20’s AND a granddaughter. Although I didn’t want to go there, my mind immediately went to the idea if I ended up with this guy, not only was I inheriting a 20+ step daughter but my young cute self would also inherit a granddaughter; kind of a turn off but a reality if I chose to continue dating these older “wiser” men. Then we had our second date. This date will forever go in the books as one of my favorite dates. He picked me up and he looked really nice. It was Saturday early evening in August. So the weather was perfect. We went to the beach and watched the sunset and just talked about everything. I felt like I was really getting to know him. I wasn’t thinking about the future and if he was husband material but I was just in the moment with a nice guy that I seemed to have things in common with. From the Sunset beach he took me to one of my favorite restaurants. Hal’s Bar and Grill in Venice. And then we ended the night at The W Hollywood laughing at all the wannabe’s in the lobby bar. We sat down and he put his arms around me and it felt really nice. We met for coffee a few days later. It was the first time in a really long time I was out with a guy consistently. We made it a point to not get sexual. Which is a good thing because it forces both people to be level-headed. Then he had the ultimate test, introduction to my closest friends at a Labor Day BBQ. That always brings a lot of anxiety because if the guy is up underneath me the whole time its annoying and if he wasn’t social and good with my inner circle of friends it would never work. You see my California inner circle of friends and I went to Hampton University together. We are all imports in California. We are truly a family. We argue, we laugh, and we support each other. And if they do not like the guy in my life then he might as well change his number and fall off a cliff. BUT “Todd” fit right in. He was able to hold his own conversation with the fellas. He also seemed like he knew my friends for years. Just like our dates, his introduction to the inner circle was seamless. A few days later me and my friends were meeting at one of our favorite brunch locations with bottomless Mimosas (The Hudson). I invited “Todd.” He left such a lasting impression on my friends that they insisted I invite him to the brunch. It had been years, literally years since I brought a new guy around my inner circle. And I have to admit it was nice to bring a date around. As me and “Todd” were walking into The Hudson it occurred to me that there was going to be a large group of people at the brunch and I hated the confusion that brought when the bill came. So I told “Todd” as we were walking in that we should ask for a separate bill. The conversation went like this.
Me: I realized we should ask the waiter for a separate check since there are so many people I don’t want us to have to deal with the drama of splitting a very large bill.
Todd: Okay cool… Um… Do you mind if we split the bill?
Me: (applying a fresh coast of lip gloss) No we don’t need to split it because we are going to get our check separately.
Todd: No I understand that part, but do you mind if you and I split the bill?
Me: (realization sinks in, look at Todd like he has two heads, blink ) Um…. Okay…
So we proceed into The Hudson. And I have various calming meditations in my head so that I do not play him in front of a group of people. I happened to find the waiter when I was on my way to the bathroom and discreetly give him my credit card and charged the whole thing to my card. We already had plans for him to come to my house 2 days later for me to cook him dinner for the first time. I had a mind to cancel but I decided to still have him over. Now let’s state the facts. The issue is not about me paying for the bill. The issue is how he did it. Had I not asked him ahead of time, was he planning on asking me in front of my friends?! Secondly we just started dating we were still in the courting phase so for him to have done something so tacky so early on says a lot. I have never had an issue paying for a meal for a guy. However, I am a little old fashioned. When I offer to pay, he should be damn near offended. This man is close to 50 and I realized that he was broke! And I’ll be damned if I dated an old ass broke man who is tacky. Now I decided to do things differently this time. Instead of cutting him off without notice I decided to have a grown up conversation with him about just to be fair. I mean we had been out several times. I enjoyed his company and I needed to figure out what was going on in his oddly shaped head! So the next day he came over to my house and I cooked him an amazing dinner. I believe I went all out just to make a damn point! As we were having dessert I decided to broach the topic.
Me: There has been something on my mind and I have struggled with whether or not I was going to bring this up. But I figured you are a cool guy and I wanted to me honest with you. You threw me off the other day when we were going into the Hudson and you asked to split the bill. (pause for reaction, an inclination that he’s getting what I’m saying)
Todd: Yeah. What was the problem?
Me: I do not have a problem paying for the bill on a date. However, the way you did it was kind of tacky. What if I hadn’t asked you before we went in about separating the bill? What would you have done when the bill came in front of my entire group of friends?
Todd: I would have asked you how you wanted to handle it.
Me: SO… you see nothing wrong with being out with my friends and asking me to pay for half the bill in front of them and we just started dating?
Todd: (with a slight attitude) No. Are you saying you expect me to always pay for the bill when we go out?
Me: No that’s not what I am saying. And if you recall I paid for our coffee. But that’s not the point. What I am saying is you and I have just started dating and you are courting me and that would not have been a good look.
Todd: Has a man NEVER asked you to pay for half the bill?
Me: Actually, no. The times when I have paid for a date, the men I am out with are usually VERY uncomfortable with that. As a matter of fact I have had to either sneak paying the bill or begged to pay. But no, I have never had a man who I am just beginning to date ASK me to pay or half the bill especially in front of my friends.
Todd: Well you’re one lucky woman because I see nothing wrong with that.
(long awkward pause)
Me: Well let me ask you this, was you asking me to pay half because you couldn’t afford to pay for it?
Todd: (long pause) Kind of… Yes…
Me: Well why did you agree to go? You shouldn’t have come if that was the case.
Todd: Well I guess you’re right.
(even longer awkward pause)
Me: Clearly we both need some time to marinate on this.
Todd: I agree.
I decided that would be our last conversation. It wasn’t a bitter “I hate your guts” type of thing but I realized we were on two different pages. Here’s the issue at hand:
1- He saw nothing wrong with the possibility of embarrassing me in front of my friends.
2- He didn’t understand that we were still in the early stages of dating and as a man he should not have asked me to pay for half. It’s one thing if I offered to pay for half or even if we had been dating for a while and we had this discussion waaaaaaay before we left for The Hudson.
3- If a man is close to 50 and his financial situation is suspect and he can’t afford a $65 brunch for two, damn it we have a problem!
4- If you are short on cash. Be creative about the dates. Let’s do a picnic, let’s go to the beach, let’s go to a museum!
I do not consider Todd to be a bad guy. As a matter of fact we are still cool and if I see him we give each other hugs and there’s nothing but love. But at the end of the day, he and I just were not meant to date.