Need advice – Pros/cons of dating him

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This topic contains 11 replies, has 1 voice, and was last updated by  T from NY 6 months, 1 week ago.

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  • #692712 Reply


    I need some advice/opinions. I am 38 years old with 2 kids – 11 & 7 years. I have been divorced for the past 5 years. While I have dated, I have not really found that special someone. Also my life is really busy and there are periods where I take a break from dating and just spend time with myself, friends and family. While I wouldn’t say I am unhappy, I do feel lonely sometimes and yearn for that special someone. I do not plan on having any more children so really not in a rush to find that someone to procreate so to speak.

    I have been on these “dating breaks” for a few months now and recently met this guy at a bar. I had gone there as they were having a live band and I love music. We ended up spending the entire night together – dancing, talking and laughing etc. etc. with each other. This was all done in a public place. I did not go back to his place or he to mine. The connection, attraction, chemistry.. everything was instant. We ended the night or should I say morning having breakfast at one of those 24 hour coffee shops and said good bye.
    He asked me out the next day as the day after he was going on a 2 month vacation which was already pre-planned with a couple of his friends. He is self-employed and in recent years has taken a step back from his consulting business to enjoy life sometimes rather than be in the rat race all the time (his words). We spent the entire next day together from noon right up until dinner. After which I wished him good night and a safe trip. He mentioned that if this trip was not already planned and paid he would have not gone and spent time trying to get to know me.

    Every time we kissed, I just didn’t want to stop. He looked quite young so I was a bit sceptical as I did not want to be with a younger guy who had yet to start a family knowing fully well that I did not want to have any more kids. When I asked him his age, he turned out to be much older than me. He even showed me his ID as I did not believe it. He is 54 years old … So 16 years older than me.

    He has gone on his vacation but we still communicate. He has expressed his desire to continue seeing me. He has told me that he is looking for long term and not really a friends with benefits or a fling and if fwb or fling is what I am in the market for then we can just be friends or cut contact completely. His physique is that of an early fit 30 year old. We have not only texted but have spoken on the phone too. He has a daughter who is about 30 years old (so an adult) while mine are still minors.

    I need some advice/opinions … am I crazy wanting to still see him even with this age gap? Mentally I found us compatible. He totally got my sense of humour and I his. Any opinions would help – good, bad and the ugly. Pros/cons to continuing this?

    #692716 Reply


    Aww reading this felt like it was from a movie scene.

    You should definitely go for it.
    Why not. see how it goes.

    Good luck

    #692720 Reply


    I am usually against age gaps, but in this case I think it is ok to proceed.

    You don’t want any more kids, he doesn’t want any more kids, he is in great shape and hopefully healthy, you have a great chemistry, there is a chance you can fall for each other and really enjoy this relationship.

    If you are looking for cons and if you are thinking long-term, 54 is one thing, 64 is another. And 74 is even more so.However some people are in a great shape at 70 and riding a bike at 75, whereas others are walking medicine cabinets at 40.

    I’d be a little careful however, you don’t know him, burning through the first stage so fast can backfire. It is a bit too much too soon, and you are not losing much by slowing things down a little. Get to know him better! Why is he single in his age? Maybe he is charismatic and charming but you don’t know if he is going to be a good BF. LOL

    #692723 Reply


    What Emma said.

    #692724 Reply


    Well he will be gone for two months, when he returns go for it.

    In the meantime be open to seeing others as well. You don’t want to get too invested in someone you briefly met.

    #692737 Reply


    Go for it! Seriously go for it!

    An age gap your age isn’t such a problem. Its when wanting a family etc is involved.

    If he looks young, he is probably fit and has good genes too. My parents had a 10 year age gap. My mum was the youngest but had terrible genes and died at 56. All my Dad’s family live into their 90s. He’s the one that’s been left alone.

    He sounds lovely. You’d be mad to pass up this opportunity but also keep a sensible head. You don’t know him and this may not go anywhere. But at least give it a try.

    #692754 Reply


    Hi, as long as you feel you are at similar life stages, and it sounds like you are… and are looking for the same thing, the age shouldn’t be an issue.

    But try to guard your heart a bit. You never know who he might meet on a 2 month trip, it’s a long time– and you guys just barely met right before he left. He sounds like an outgoing, friendly man, since he managed to pick you up, haha. So just be aware…. you don’t have a commitment. Try not to get carried awa until he’s back and you can get to know each other, and try to stay open to various possibilities including that you might “lose steam” or momentum with him being gone that long! That’s the biggest thing I worry about here.

    #692815 Reply


    Thank you ladies. You are right. It is just that I have never felt like this with anyone including my ex-husband. And it is freaking me out. And when something freaks me out my defense mechanism kicks in to run and hide somewhere. You are right … I could meet someone equally or more amazing in the next 2 months or he could. And this could fizzle out into nothing. I am aware that he could very well be like my ex-husband and be all talk and no action. But whatever happens I will always have a fond memory of that night and the next day.

    I do wonder if we are in similar life stages though. Especially since his daughter is an adult and my kids are not even teens. He lives alone and mine live with me half the time.

    Sugar – yes it does seem like a movie scene and hence I sometimes do not even believe that I had met him till I actually see his message.

    Emma – He has told me that it seemed like he could very easily fall in love with me. I do not really put much stock into words as my ex-husband was all talk and no action. I actually told him to enjoy his vacation and no point building castles at this point. That once he comes back, we can spend time getting to know each other. Frankly speaking, it looks like as if he is in better shape than me even though he is much older. When we were on the date the next day, at one point he pulled me onto his lap and kissed me and it was just so romantic. And at another point when we were indoors (still public place), I mentioned something about me weighing a ton or some such thing. And he actually carried me to “check” how much I weighed and it made me feel light as a feather.

    Our meeting and dates and messages have just clicked and seemed so right that I am finding it difficult to actually believe that someone is not just playing an ugly joke on me. I am currently on a “dating break” as it is a really busy time of the year for me at work and with my kids. And the very thought of going online and taking time from my very busy schedule to meet new people doesn’t really sit right with me at the moment. I would rather spend the little free time that I have either catching up on my TV series or meeting up with friends. The pace should slow down in June and during the summer. And if this fizzles out, then I will look into dating then or maybe just spend a year to enjoy my friends’ and my company unless loneliness catches up to me first.

    #692831 Reply


    My bf’s first and only other gf was 16 years older. Had she not died after 6 years together, they’d still be happy together now, I’m sure of it.

    Go for it, life is short.

    #692837 Reply


    If you are late 30’s and he is a fit 54, you are probably the age range he normally dates. My city? Guys who look good in their 50’s date women in their 30’s.

    #692847 Reply


    Just don’t text too much while he is gone. Try to limit it. Also, don’t make up in your head how perfect he is. We all have our flaws. he could chew with his mouth open, or only eat fast food, or have smelly feet, or be watch so much TV you cant stand it, etc.

    Wait until you get to know him much better. dont rush things.

    #692936 Reply

    T from NY

    Go for it!! Though…

    I will say though — telling you he could fall in love with you after only meeting up a couple of times is a pink flag for me. He doesn’t even know you. Physical appearance and chemistry does NOT a healthy relationship make. I would be extra careful about when you choose to sleep with him and try to establish a friendship first, if you actually want to explore this going somewhere.

    Remember — most relationships that start out hot as a comet burn out just as fast. Pace it. And continue to have FUN!!

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