Need relationship advice

[Anonyname]

Gina wrote to me in June 2012. I was briefly dating another woman at the time and didn’t respond. Two weeks later this other woman broke up with me and about the same time Gina wrote to me again out of the blue. I mentioned the break-up and Gina was supportive and very nice to me. We wrote and texted for weeks. I lived about 45 minutes away from her at the time. One night she dared me to come out to her house and put a rose on her car. I did and she spoke to me through her upstairs window but wouldn’t come down to see me. It all seemed kind of romantic at the time.

We met again a week later at a park in her town. She was a very interesting person, highly sensual, somewhat childlike, a bit of a tease. We texted for weeks afterwards. Most of it dealt with how she didn’t sleep around, and she didn’t have time to date because of her two jobs and 4 kids. Somewhere along the way, I mentioned that if I had a girlfriend I could help her financially. We eventually came to an agreement where I would meet her in a hotel room and have sex for $200. I felt fortunate to break my one year dry spell and didn’t really expect it to become a regular thing.

We have met pretty much twice a week since then. I have almost always paid her varying amounts from $50 to $200. She has a pretty severe problem with prescription drugs and alcohol. Sometimes she would literally pass out in the room. She also would lie about stupid little things. I also found out that she had met up with past boyfriends on at least several occasions for sex. She has always been very secretive about her time and whereabouts. She deletes all of her text messages. She used to text naked pictures of herself to other men and they would reciprocate. She seemed to really enjoy the attention. She brags constantly about the attention she gets from men and shows me their naked pictures. She has remained on dating site all this time.

So this has been going on for 8 months now. One time the condom broke, so we stopped using them several months ago. She had her tubes tied so there is no risk of pregnancy. I have moved an additional 45 minutes away now. Between the cost of the room, helping her financially, buying her drinks, meals and gifts, it has become very expensive, not to mention the travel time and time away from my home is disruptive to my life.

The sex is fair. She doesn’t do a lot of things in bed. She won’t let me see her completely naked. She doesn’t like to kiss. We just talk, cuddle, and have intercourse and that’s about it. Occasionally I go down on her. I am not sure she has ever even orgasmed during all this time. She has made it clear that we will never be a couple in the traditional sense.

As for me, I am 48 years old and divorced. I haven’t dated much in the last 15 years and really don’t enjoy dating at all. I work in a cubicle and rarely leave the house except to work. I am a homebody, and somewhat socially anxious. I dislike talking on the phone. I am not unattractive, but I think my personality is rather bland and boring. I am finding myself to be very lonely despite having Gina in my life. I long for a real, loving, committed relationship but have all but given up hope. I am tired of being broke all the time because of the financial demands of this relationship. But I fear giving it up because I have nothing better, and no real prospects for the future. This is all making me feel depressed. So I would like to hear some advice about what I should do. Any input would be appreciated.

[FlaCooln]

I think you have an unhealthy relationship with this woman and there is no future with her. Also, you are having unprotected sex with someone who you are not committed to and is probably sleeping around. If you like Gina I would discuss how you are feeling with her. But, you should probably move on as I think she is only about the money.

[michelle23]

this is not a relationship. She is a prostitute and you are her client. She feels nothing for you, is repulsed having sex with you which is y she doesnt orgasm or kiss you.
Also you could easily catch an sti/sti off her. I think you should cut all contact with her and get yourself tested

Y are you settling for this? Would you try online dating to meet a woman who wants the same things as you?

[pcmaster]

You was lonely.

[Anonyname]

It probably is an unhealthy relationship, but it is kinda better than nothing, which is what I have had for a long time. I agree the unprotected sex isn't very smart, but it really feels much better than using a condom. The natural feeling is really a plus for me. She has said she is only in it for the money, and she says she thinks I am only in it for the sex, which is probably true for the most part. But she has also said she has feelings for me (whatever that means), and I think about her alot. I have even met her kids, and she doesn't usually bring men to her house. Even though I hate the expense, there would be expenses in dating someone else, and I may not have what I do now with someone else. True, there is a potential for a much better relationships with someone else, but there is also a chance that I could have nothing for years again.

[Anonyname]

this is not a relationship. She is a prostitute and you are her client. She feels nothing for you, is repulsed having sex with you which is y she doesnt orgasm or kiss you.
Also you could easily catch an sti/sti off her. I think you should cut all contact with her and get yourself tested

Y are you settling for this? Would you try online dating to meet a woman who wants the same things as you?

I met her on an online dating site. I have met several women on these sites, it usually doesn't go anywhere. I don't think she is a prostitute. She said she has never done anything like this before. She has said she enjoys the sex, even though she doesn't orgasm. She said she doesn't orgasm because of some of the medications she takes. I can sometimes convince her to kiss for a minute. She likes to cuddle and talk. Occasional we will play cards. Sometimes I pick her up at her house, and I have met her kids, who seem to like me. I always get us a hotel room because her kids are teenagers and they are always home, so we can't fool around there. Anyway she likes to get away from them and get drunk with someone. She has said she cares about me and has feelings for me, but she has also said we can never be more than we are now because I live too far away (80 miles). I still manage to see her twice a week despite the distance and the expense, but it is all on me and it takes all of my spare money to keep this up.

Why am I settling for this? Because it is better than nothing. I was married once and had two kids living with us, a 3-bedroom house, 2 cars and everything. After my divorce, I have always felt like a failure. I want to be loved and I want to be cherished again, but that doesn't happen overnight and it is so hard to wait for something and hope for something that doesn't materialize. I hate the situation I am in, but at least I have someone to cuddle and make love to a couple of times a week. Frankly, I don't know why a woman would want me anyway. I am not much fun, and all I do is work. I just don't know what to do. It is hard to drop even a bad relationship, for nothing at all.

[bearz]

She might not be a prostitute, but she is making you pay for sex. She doesn't have any honest feelings for you and by keeping this going you are just encouraging her bad behavior. She has issues that she needs to deal with and you giving her money isn't helping at all - and neither it is helping you since you're pretty much broke now. You need to have a talk with her and stop this. I'm pretty sure if you tell her you can't pay her anymore, that'll be the last you will see and hear from her. You need to find yourself someone who isn't after only one thing, money.

[Anonyname]

You was lonely.

Yea, I was lonely. I am still lonely much of the time. At least when I am with her, I don't feel lonely for a few hours. The problem is it is so expensive to keep this up. I have some social anxiety too, so it is hard to meet people. I guess I need to work on that.

[Anonyname]

She might not be a prostitute, but she is making you pay for sex. She doesn't have any honest feelings for you and by keeping this going you are just encouraging her bad behavior. She has issues that she needs to deal with and you giving her money isn't helping at all - and neither it is helping you since you're pretty much broke now. You need to have a talk with her and stop this. I'm pretty sure if you tell her you can't pay her anymore, that'll be the last you will see and hear from her. You need to find yourself someone who isn't after only one thing, money.

This is true. She has said she wouldn't see me if I stopped paying her. But I have also told her I wouldn't pay her if we didn't have sex. So she gets her money, and I get sex. But, yea, it kinda sucks because I know it isn't going anywhere, and she really isnt the kind of girl I would want to settle down with. It is hard to end it though. The sex gives me some confidence and actually makes me feel calm and happy for a few days, but then it goes away and the loneliness and sadness sets in again. And I know I can make it feel good again just by giving up the cash. But deep down inside, I know it isn't supposed to be this way. And maybe I am actually hurting myself somehow.

[FlaCooln]

Dude, cut off contact with her, get tested, and ask out a local woman. Nothing good can come out of this "relationship."

[leegmoser]

I read all of your conversation. And I think it seems not a harmful connection with this lady and there is no upcoming with her. If you like Gina I would talk about how you are sensation with her. But, you should probably shift on as I think she is only about the hard cash. Also, you are having unsecured sex with someone who you are not dedicated to and is probably getting to sleep around.