A
male
age
36-40,
anonymous
writes:Dear Cupid,I've been seeing a prostitute for some time now. When I started seeing her, I was in a very bad place emotionally (borderline depression, work pressure, family issues). We didn't have sex on the first few "dates". We mainly talked and cuddled, as it was what I most needed. She soon started talking to me about her own life and issues. Most of our encounters went for longer than what I had paid for: I always paid for 1 hour, and she spent 2 to 4 hours with me. At some point, we started having sex too, but also going out for lunch or dinner before/after that. I paid for that. I've been seeing her once every two months on average.After getting my life in order, I wanted to stop seeing her. It's not that I felt much guilt or anything, but I want to find an actual girlfriend. I was afraid that seeing her held me back from making efforts necessary to meet someone. Yet, I kept seeing her. I realized that what I missed was not the sex, nor the emotional support, but simply talking, cuddling, laughing together, caring about her life, etc. I believed I was just another client to her and that if I stopped being her client, I'd simply loose her. I finally told her that I wanted to stop seeing her, but I couldn't bring myself to it. She proposed we go out as friends.We've been getting together for a few weeks now, having coffee or a drink, going to see a movie, etc. simple stuff really. She insists to pay her share, to establish that we're seeing each other without monetary transactions.I'm very conflicted now. I obviously feel deeply physically and emotionally attracted to her. I don't know her expectations of our relationship. I know she's very isolated: most people close to her left her when she started as a sex-worker. I know she needs friends and support. I honestly don't know if she'd like me to be her intermittent lover, her boyfriend or stay a platonic friend.On one hand, I feel like she's giving me signals that it's OK if I try to seduce her. On the other hand, these might be habits leftover from our previous relationship, or just wishful thinking on my side. Anyway, I'd feel like I'd be betraying her trust if I tried to move things into a relationship involving sex. I'd also feel like I'd be somehow taking advantage of her, getting something I don't actually deserve for free. I feel like she's way out of my league, that she could have a lot better than me.She's a classy girl. Her rates are high, she gets more than enough clients. Most of them are far more rich than I'll ever be. She's planned her way out of that line of work. She doesn't need my money now, nor will she need it anytime soon. I entirely trust her on that side.I'm fine being her platonic friend, if that's indeed what she wants, but I'm afraid to miss an opportunity.So:I don't know how I can broach the subject with her.I don't know if I should broach the subject at all, or simply grit my teeth, wait and see how things evolve.Or maybe I shouldn't talk about it, but try seducing her like any other woman I'd date, but I'm afraid emotional involvement is already too deep for me to keep a cold head. I'm also afraid going that direction makes the current situation uncomfortable to her, putting an end to everything.
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, anonymous, writes (14 December 2018): Talk to her about how you feel.
I think she really likes you and wants to feel that she is with a man who treats her primarily as a friend and confident, not just for her body or for sex.
She wants things to be equal between you, that's why she's paying her share. She doesn't want to feel 'paid for' by you, because she genuinely likes you.
Talk to her about your feelings and take it slow with her.
You have both been through some difficult times, but it seems like you two could really become very special to one another.
A
male
reader, anonymous, writes (13 December 2018): Well I suppose you know the cliche question most clients ask a prostitute they are with. What is a nice girl like you doing in a place like this. And the answer invariably is, I am waiting for the right man to come and take me out of here. Of course that is not true. The real answer is, she is there for the easy money. Sex becomes a business to her. There are no emotions or pleasures involve. That is why a prostitute's nightmare is a well endowed customer because of the obvious physical pain she has to endure. My advice as a guy is why get yourself involved in a complicated situation like that whose outcome for you would only be pain and hurt. To her sex is business, to you it is love and affection. Big difference.
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A
female
reader, Andie's Thoughts  +, writes (12 December 2018):
 It’s not the right time for you to date. You need to seek therapy until you’re mentally well again. You can’t be in a healthy relationship without being mentally healthy yourself.
Not only that, but what if she dates you and keeps her job? What if she dates you, but you can’t stop thinking about all of the other guys?
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A
female
reader, janniepeg  +, writes (12 December 2018):
 There are 3 outcomes. She became your girlfriend. She is just your friend but still have to pay for sex. She doesn't want any business with you anymore. I don't know why you would limit yourself to just 3 lousy options. You said she could do a lot better than you. That says a lot about your self esteem. I think you have to work on your own issues before even starting to date. So you don't feel you have to settle for just any girl. A sour relationship can make your life worse than before
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