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I sunk $1,000 into this failed relationship

Dating can be expensive. Just ask this letter writer.
Dating can be expensive. Just ask this letter writer.Xaume Olleros/Bloomberg

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Q. I met a woman online in September. I live in an isolated area, six hours from where she lives, so I agreed to come to her city whenever we met. We met on three different weekends, two in October and one in December. It was really strange. We only texted in between visits, and whenever we met, we only spent time in a hotel room. The only time we were together outside the hotel was at a gas station.

I understood her desire for privacy and didn’t question it. During the second weekend we met, she said she was in need of money. I was hesitant, but I gave her $200 without asking her to pay me back. When we met in December, I bought her a nice dinner and a few small things for Christmas to help her feel better. She also asked for champagne the second and third times we met, and I acquiesced, although nothing extravagant.

The weekend after Christmas, I paid for her and her daughter to stay in a room at the hotel, since the room had a hot tub. I also paid for their dinner. By the time all was said and done, I had sunk over $1,000 into this, even though we had never gone out in public, never talked on the phone, nothing else. Around Valentine’s Day, she asked me if I was sending her flowers and/or chocolates. At first, I said I would, but then said I couldn’t because (a) I was expecting a large hospital bill and (b) I thought I would have to pay a lot in income taxes. She called me a liar, told me she was blocking me, and cut off all contact. I replied, telling her I would forget what she said and be there if she wanted to talk again.


I haven’t heard from her since. One side of me is lonely and thinking I’m a mean jerk. The other side tells me I did the right thing. I am very socially awkward. I am autistic. It makes meeting others very difficult. Add in living in a very isolated place and it feels beyond hopeless. What would you suggest? Thank you for listening. I’m sorry I went on so long.



A. 1. You did not go on for so long. We’ve had letters twice this length. It’s OK.

2. I’m sorry this experience wasn’t better for you. It sounds very disappointing and hurtful.

3. You were not a mean jerk. You went out of your way to get to know this woman, to please her, and she did not reciprocate. She expected so much and offered very little. The minute you were honest about your own needs, she was cruel — and then bailed on you. Please know that it’s good she’s out of your life. You want a partner who is honest and kind. She doesn’t qualify. It’s OK to drive to see someone, but it should feel like they’re working to make the process easier for you too.

4. It sounds like you’d benefit from more community where you live. At the very least, it would be nice to have one or two friends who can help you navigate this process. Your area is remote and small, but ... are there ways you can get involved with activities? Book clubs? (That would be my go-to.) Any spots where you might be able to socialize and feel involved? Dating is a little easier when you have one or two friends who will be there for you, no matter what happens. It feels less hopeless when you have companions, even if they’re people you talk to online.


5. Also, therapy is nice if you can find it. Mental health professionals can teach you to navigate this stuff too. It can absolutely help you learn to trust your gut.

And let’s remember that your gut has been throwing red flags since this started. It told you the hotel stuff felt weird. It told you to stop spending so much time and money on this woman. Your gut said, “This doesn’t feel good!”

Good for your gut. Having that inner compass seems pretty hopeful to me.



Women like the one you describe play on your feelings so you will feel mean and give her what she wants. Here’s a tip: Never ever give money and/or gifts to someone who asks right after you meet them.


There are people out there who are only in relationships for what they can get. A relationship should be give and take, not just take. This lady was one of them, and now you know how to identify them.



^Not only relationships, but friendships too.


I’m sorry. You are anything but a mean jerk. You are too nice and trusting. And I think if you can move into a less isolated area, you might want to do so. Good luck.


Consider yourself lucky she’s gone. She was definitely taking advantage of your emotions and your wallet. If she gets in touch with you, don’t respond to her. Block her number. She does not have good intentions. Focus on enjoying your life where you live and maybe meeting someone local. Perhaps you could join a church group or club involving a hobby you enjoy. You are learning from past experiences and that’s important as you move forward. Best of luck!


I would suggest avoiding online dating. You might do better to meet someone through friends or family, or through your church, if you belong to one, or other in-person activities.


At some point we all get taken advantage of by someone. It’s not just because of the disadvantages you list that made you a target. Your feelings are normal, and your response to her (flowers, chocolates) was the right response. You are not a mean jerk. You showed wisdom. I hope that knowledge helps the hurt feelings go away.




Send your own relationship and dating questions to loveletters@globe.com. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.