Letting ‘Em Down Easy

After the disastrous date last weekend with the guy who talks to dead people about Trump being re-elected, I decided not to give up and get back up on the proverbial horse. Why I don’t know. Maybe because I have a different outlook on dating. Maybe because it makes for really juicy stories. Either way, I kept on swiping. I landed on a few men that have some potential. There was Carlos from Dorchester (which I mentioned last week). Steve the widower. Lloyd the smoother talker. Roger the firefighter. All pretty attractive and over 6 feet (a real plus for me).

Normally, I take a back seat and let a man make a move, but I’ve decided that I need to take charge a little and stand out from the crowd. After all, you are one of the thousands on these dating sites and just like me, you want to feel “special”. I’m approaching dating this time with an open mind, open heart and a curiosity to meet new people. Even though initially I get really nervous on a first date, I actually love meeting new people and finding out what makes them tick.

This time around the hamster wheel of dating, I’m going to get out there and date multiple people and not get stuck on one guy that may turn out to be a disappointment. I hate to admit that I watch the Bachelor but I actually love it. My daughter and I find it fascinating watching all the dynamics of dating unfold in front of millions of people. I admit I can’t stand when women get catty competing for one guy but I love it when the roles are reversed on the Bachelorette. Our new obsession is Love is Blind on Netflix. It is a dating experiment like no other. A group of people is sequestered to a room where they can only hear each other in the “pods” as they call it. Without seeing each other, they fall in love and have to be engaged in order to move on in the experiment. It’s absolutely ridiculous and fascinating at the same time. The romantic in me loves it while the skeptic thinks it’s a stupid idea.

Anyway, back to my story. With an open mind and an open heart, I make a connection with Steve the widower and the polar opposite of him, Lloyd the smooth talker. Steve is an older gentleman with a big heart and Lloyd is younger and well, most likely a player. The jury is still out. Both are texting me throughout the day along with the other two and I’m starting to mix them up and lose track of who’s who because I have five other conversations going on two different dating sites. It’s exhausting. I decide I have to stop swiping and try to make connections with the matches I already have. I can’t keep up so I create a bio page for each one. I know it sounds awful but it’s necessary. Don’t judge me.

Steve the widower asks me out and so does Lloyd but he’s away on vacation in Jamaica this weekend. He asked me to meet him on the beach and I would have done it in a second if he were buying my ticket. Needless to say, he didn’t.

I met Steve out for dinner last night. He picks a nice little restaurant with great food. Already scored a few points for not picking the 99 Restaurant. This guy is a consummate gentleman. Insisted on opening doors, helping me with my coat and pulling out my chair. Old fashion charm gets me every time. He’s a little awkward and overly eager but cute.

We sit at the bar and order a drink. He’s excited and bubbly diving right into a conversation about all the things he did that day. I’m trying to ignore the fact that he has bad breath and focus on finding a connection. I quickly realize that although he’s the sweetest man I’ve ever met, were not a match. It’s hard to explain why…it’s just a feeling. He’s attractive and kind of smart but not very intellectual. He struggles to find words and the conversation is all over the place. I give him the benefit of the doubt because I can jump around in a conversation myself and I think maybe he’s just nervous. The twelve-year age difference is very apparent. He is definitely old-school and not very progressive.

In fact, the one big red flag for me was that he was a conservative in his profile. Those of you that know me well understand that is a deal-breaker normally but I’m trying to branch out and be more open-minded. The next red flag came when I asked him what he does for work. On his profile, it said he was a CEO for a real estate company. Turns out, he’s unemployed. In fact, his last job was for a tire company. I’m confused but I didn’t want to pry since I’m not exactly loving my career at the moment either. Why would he lie on his profile? He seemed like such an honest straightforward kind of man. It seems strange to me because it seems like he lives comfortably but he hasn’t held down a job in a while. He tells me his wife worked and he was a stay at home dad working odd jobs here and there. Which is fine but why portrait yourself as a CEO? I know what you all must be thinking—he’s a con artist who lives off his wife’s insurance policy. Well, that’s exactly what I was thinking. Here I am bored out of my mind and this guy is clearly into me. Planning our next date and telling me how much he’s enjoying our date. He seems really sincere and very sweet but he’s corny as hell. His jokes are not landing yet he cracks himself up. It’s hard to fake that I’m laughing along with him. The whole time I’m thinking when is this going to end? Meanwhile, he’s telling me he’s having the best time trying to hold my hand looking deeply into my eyes.  He even got emotional a few times talking about the kindness of friends and neighbors and how it’s important to give back to people. I don’t think he’s a con artist but something is not adding up. I think I watch too much Dateline.

I offer to split the bill (something I never do) and he insisted on paying. He says, “How about you get the next one?” I tell him he’s slick trying to ask me on a second date. Oddly enough, I agreed. I don’t know why the hell I did that. I’m definitely not interested in a relationship with him, but he was so into me and I felt that I could at least give him another chance before I let him down easy. Normally, I cut it off on the first date if I know I not attracted to them, but I’m trying to be more open-minded remember? I’m trying to give men a fair shot before I cut it off completely. The other reason is that I suck at disappointing people. I have the hardest time “Letting ‘em down easy”. Even the last weirdo was hard. I had to tell him the next day that I wasn’t interested and I hate it. You would think it would be easy for me by now but it never is. I’ll go out with him one more time, get the answers I want about why he lied on his profile and how his wife died. Yes, just like a crime scene investigator.

Wish me luck on my next adventure with Lloyd the sweet talker who’s sending me kissy faces from Jamaica. Good Lord—dating really does suck. I keep telling my self and other women that reach out to me, “You only need one.” You might have to kiss a dozen frogs to find him but you only need one. My search continues with an open mind and an open heart. I’m not going to let disappointments and the difficulty of letting ‘em down easy prevent me from finding the one. I will continue on my journey to finding love and I will find more of myself along the way.

With Faith, Hope and Love,