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How to Have an Online Relationship/Online dating / age difference / long distance


QUESTION: Hi! I hope you're doing well!

I know this is going to sound really long and complicated, but I'll try to explain it as well as I can. There's a lot of categories this could fall under but I liked what I read in your profile so I thought I'd ask you.

I'm 21 years old. I'm from Milwaukee, WI and I go to college in a town about 100 miles north of there. When I was 18, I started chatting with a guy online. It was purely by chance. But he seemed really nice and we flirted a bit. Eventually our chats became more and more frequent, nearly every day. After a couple months we exchanged photos of ourselves(nothing sexual) and we both found each other very physically attractive. But most of all we just enjoyed having someone to talk to and flirt with. A few months after that we started having audio chats. After a little over a year we started exchanging photos that were a bit racier. After being in contact for about 2 years we exchanged phone numbers and started having phone calls 3-4 times per week. A few months ago we started having video chats.

We both really like each other. We've talked about almost everything and we've shared some really personal things with each other. I trust him a lot considering we haven't met yet, and he's given me great advice on lots of different topics.

He's 41 years old, single, never married, with a 7 year old daughter. He lives in Detroit, MI. We've wanted to meet in person for quite some time but I've been busy with work and school and he's busy working and being a full-time dad (he's had full custody since birth and the mother is no longer living). But we finally both have a weekend free so we've decided to meet at a half-way point in Indiana. Since it's such a long drive, we're meeting in the early afternoon for lunch, spending the afternoon together, having dinner, and spending the night at a hotel. We will be sharing a room.

Although I've wanted to meet him for a long time, I've always been nervous about the idea. I was date raped when I was 16, so I'm very suspicious of men. But we've been talking almost daily for over 3 years now. I've even gotten a full background check on him and he has no criminal record. The only thing he's been to court for is custody of his daughter. I know where he lives and where he's lived in the past. He doesn't have a Facebook profile, but some of his family members do and I've browsed through their information and pictures and of him and he seems like a totally normal, family oriented guy. I know it may sound really weird that I've done so much checking up on him, but I want to be as cautious as possible.

Neither of us has any experience with online dating or long-term relationships. He's never dated anyone younger than him, and I've never dated anyone more than 3 years older than me. So this is new to both of us. So my question is this: would it be okay for us to give each other oral sex on our first night, if we were both comfortable and felt right? I'm torn, because I've never considered myself the type to do anything sexual on a first date. I've only ever done anything sexual with one person, and that was the guy who raped me. As of now I would like to wait until I'm married to have intercourse, and he knows this. On the other hand, I feel like the fact that we've been talking for over 3 years makes a difference. It's not like we just bumped into each other at the bar and decided to go home and get naked together. We do know a lot about each other. He says he does not believe in one night stands, friends with benefits or online hook-ups just for sex. But he assures me that if we did do anything it would be different because we've been talking so long and that he would not think I was a "slut" since sex is not the purpose for our meeting. He has only been sexual with 2 women in the past, both of which were long-term relationships. He has not STDs or anything like that. He's made it very clear that sex is not one of his main priorities. He knows that I'm a bit nervous about sex because of my past and I have no worries about him trying to seduce me. He's very respectful. He says although he will likely be up for anything besides intercourse, it is totally my choice whether or not I want to do anything. I'm just concerned, because I really do want us to give each other oral sex. I think about it a lot. I just never imagined doing it on a first date before. Also, he would be the first man to give me an orgasm. I know I would love it, I just don't know how I would feel afterward. I want him to know that if it happens, I'm likely to feel even more attached to him than I already do and he will be important to me forever. Sometimes I think that NOT doing anything sexual would make it more exciting the next time. But sometimes I think I would regret not doing it when I had the chance. And I don't know when we will see each other again after that. I've actually wanted to live in Detroit since before we ever started talking, but I don't know how soon I will be able to do that.

I know there's a lot to consider here, but I would like your honest opinion on all of this. I'm only 21 and I want to explore things and learn about myself and gain experience, but I also want to be careful and avoid mistakes. We think alike, have similar backgrounds, morals, and goals in life. We like a lot of the same things. He's a real gentleman, not like most of the guys my age. He's taught me a lot about guys and life in general. Any tips or advice would be much appreciated!


ANSWER: Hello, Rachel.

Your question brings up many questions for me to ponder. One is why you believe everything he has written you and you haven't even met him to see if he is worthy of your trust top spend the night with on written words alone....DANGEROUS!

For someone who was date raped, you seem exceptionally trusting. Please reconsider whether you would hypothetically let your 21 year old daughter do what you are considering, in order to get some perspective on this.

Secondly, a 41 year old man interested in a 21 year old girl for more than sex or other motive even darker would be odd. There will be very little in common for a long relationship based on mutual interests, beliefs, backgrounds and history,  and in 20 years when you are 41 he will be 61...and beginning his elderly slowing down phase as you are entering your prime.

I could go into all of this that you wrote, but the main points I want you to consider is WHY you would pursue this and also, please review your past relationship with your father for answers. A much older man might be a temporary panacea for a daddy complex, but it won't make for a happy long term union. I see much heartache and regret, if you pursue.

---------- FOLLOW-UP ----------

QUESTION: Hi Sonya. Thanks for your response. I must admit, I'm not surprised by the concerns you mentioned. I can answer some of your questions though.

Initially, I did not always believe everything he wrote to me. Which is why, even after two years, I got a full background check on him. Everything was perfectly clean.

It wasn't based only on written words. We had hundreds of phone calls and dozens of video chats.

I'm not very trusting. Not even of my own family, especially men. I myself am amazed at the level of trust I have in him.  

And yes, I would let my 21 year old daughter date an older man. Of course I would want her to be very cautious, but since I have been in that situation, I understand. I myself used to be very judgmental of couples with even a ten year age gap. But because our date went extremely well, I fully believe that there are some wonderful, trustworthy older men. My date with him went better than any date in my past, ever. He showed the best manners of probably anyone I know. He had a clean sense of humor. He wasn't arrogant. He didn't try talking dirty. We even went to Mass before dinner.

And surprisingly, we do have quite a bit in common. I know that's probably hard to believe. Of course he has much more life experience than I do. But we do have many common interests and beliefs. And our family backgrounds are quite similar.

And I have thought about my relationship with my father. It has never been great. In fact, when I first started talking to this guy, I did look up to him like a father figure. And he knew it. Whenever I was contemplating a problem, I asked him for possible solutions. And whenever I followed his advice, things worked out well. But in the last year and a half my relationship with my father has improved considerably. I no longer see this man as a father figure. I still ask for his advice, and I do believe his daughter is extremely lucky to have him. But being with him in person did not feel awkward at all, even though I suspected it might. It felt normal, like any other date, but ten times better.

He says he doesn't mind the age difference because he still feels the way he did in his 20s, just a lot smarter. He likes that I'm energetic and fun. I am the only person he's dated that is younger than him. He feels that most women his age and older are predictable, closed-minded, very set in their ways, and not adventuresome.



I went over this with you one time, and do understand your attraction to a point. That is why I gave you the answer I did.

Please know background checks are for those who have records. The vast majority of serial offenders have no such records and weren't arrested.... they are "Good" at avoiding this. It doesn't automatically mean they are safe, if his record is clean, it also can mean he is an exceptionally good con. This also means he is twice as dangerous.

It isn't normal nor should you think it is, for this relationship to be desirable for him OR you....this is an abnormal situation, and you don't know why.

You have to choose what you will do, but whatever it is, don't say you weren't warned. My advice is to walk away and have no contact. Unfortunately, I see a broken young lady in your future.  

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Sonya Snyder


All questions from how to, to warnings about how not to communicate on line. Offering best and worst case scenarios and suggestions for being safe, and succeeding in, on line dating.


21-year study into the minds of abnormal behavior, and also an on-line dating specialist in the psychological profiles of this new form of dating. Predators abound on the internet - How to spot them is a specialty of mine for readers concerned about who they are conversing with. One in 16 people is a sociopath in the USA - the vast majority are not murderers, but are predatory cons who prey on unsuspecting children, men and women for primarily money, sex and other forms of manipulation and control. Serial sociopathic con artists and offenders in everyday life are responsible for many forms of financial, emotional, physical, psychological and environmental abuse, child abuse, date rape, and domestic violence, which costs the USA $4 Billion dollars annually to repair damage to victims. I am an advocate for safer surfing through on-line dating.

BA in Journalism, and completing MA in Forensic Psychology, specializing in abnormal psychological profiles. Detailing a thesis for a nation-wide school age/classroom program to protect students from future serial offender interaction, by giving them the insight and knowledge to be able to "spot" the signs and classic methods of operation of such individuals who function around us on dating sites and in our every day lives.

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