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I have a recurring dating dilemma. I meet a guy and he asks for my number, sometimes we go out and sometimes he never does ask me out. Almost always the man just stops talking to me after maybe two weeks; sometimes months go by and I’ll receive a random text of desperation: “Hi, what happened to you? I had so much going on in my personal life at the time, but I’m ready to pursue you if you are still single.” I can’t tell you how many times I have received this text. I want to tell the guy to kick rocks, but I never do. I just take a bow. Should I ever give a man the time of day if he wasn’t willing to do that for me? — Taking a Bow

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red light

I am a 21-year-old guy and up until earlier this year I was still a virgin. I get a good amount of attention from women when I do get out, but, without going into too much detail, I do not date a lot because of my crazy busy work/life circumstances. I was a late-bloomer and didn’t really start dating until this year, and I only got my first kiss last year at 20. I had a few chances to lose my virginity with different women I had been seeing, but, embarrassingly, nerves kept me from performing each time.

Now all of my friends have been sexually active for years and there’s always been jokes and pressure to get started, and they didn’t really understand my situation. I also work in a workplace — the military — that is the very definition of hyper-masculinity, where there is an expectation to be sexually-active and where I have experienced and witnessed others being put down for being sexually inexperienced.

Here’s the bad part: Recently, on a trip to Europe with friends, we made a stop in Amsterdam and, after a night of partying, alcohol, and a little bit of encouragement from my friends, I slept with one of the women in the red light district. I guess my thought process at the time was that I just wanted to experience sex and see first-hand what the whole fuss was all about. I had also been feeling bad about my past failures and really wanted to get the first one out of the way.

The whole experience, while the woman was friendly and nice and I tried my best to be respectful and polite, was underwhelming and left me feeling terrible. I feel so ashamed over what I have done. The act itself was so mechanical and hollow and devoid of any emotions. I often lie awake in my bed and wonder about what led the woman I slept with to enter that line of work. I know Amsterdam’s RLD is legal; however, I just feel horrible if I took advantage of her circumstances or something like that. I never thought I would be the type of person to pay for sex, and I feel terrible knowing how disappointed and disgusted some people in my life, like my sister and mother, would be with me if they knew. I feel like I let them down, but most of all I let myself down.

The sex was safe, a condom was used for everything, and I tested clean a few weeks after and will be tested again in a few months to ensure I am clean. I just don’t know how I am going to get back into dating after this. I feel like I am tainted or carrying this huge shame around with me and that, as soon as any woman I date asks about my sexual history or first time and finds out what I did, she will be gone.

How should I approach this in future relationships when the topic of sexual history comes up? I just can’t help but feel that this will be a deal-breaker for most women. I can’t justify it to myself, so I would be hopeless explaining it to a significant other. I am an extremely honest person and couldn’t lie. In the past, girls I was seeing never asked but this was always in casual relationships, and I feel that in a serious relationship this is bound to come up.

I think about this daily and it’s really bothering me. I feel like this one act has completely changed my life. — Ashamed of Sleeping with a Hooker

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This week in the forums we’re discussing:

Defriended IRL via email

Addie Pray’s big, big news

Another Question On Getting Engaged

He lied about when he got divorced

Going dutch on dates

First Time Car Buyer!

Engagement Rings

“My Boyfriend’s Mother Controls Everything”

Health and fitness

(epic) I have a MAJOR crush on my married boss!

So…I got an email trying to break up my marriage…

Need Relationship Advice ASAP

I am bothered by my husband’s Instagram use

Words of advice for someone who’s turning 22


NYC – March 20

Boston — March 23-26?

Follow along on Facebook, Twitter, and Instagram.

If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


Broken Engagement

Longtime reader here and your post on engagement rings is timely. The other day I tried to break up with my boyfriend of one year. However, during the breakup, he pulled out the engagement ring he bought and proposed. I ended up walking back on the break-up because I felt so guilty.

But now, as a few days have passed, I am really mad. We had talked about marriage before, but I asked him not to buy an engagement ring. One big reason was I was having doubts about our relationship and another reason was he couldn’t afford the ring.

Now I feel stuck. He went into debt for a ring I wasn’t ready for and now really don’t want, and I can’t stop feeling guilty. Do I give him another chance or do I really break up with him? What do we do with the ring? — Yes By Guilt

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wedding proposalOver in the forums there are a couple of discussions going on regarding engagements (and proposals) and engagement rings, and I thought it was worth bringing the topics over to the main page for deeper thought. First: engagements. It’s the 21st century. What do you think about this idea of women waiting around for their men to propose to them? I mean, on one hand there’s a place for tradition and, if both partners like the idea of the dude down on bended knee (or if one is really into the idea and the other is willing to go along with it), then they should go for it.

I myself had a traditional proposal where Drew popped the question to me, but we had had numerous conversations leading up to it and were on the same page — and I’d even given him my great-grandmother’s engagement ring and told him to give it back to me when he was ready (knowing very well he was ready and it was just a matter of his figuring out a way to propose; we’d also discussed a summer wedding, so I knew I wouldn’t be waiting very long for a proposal). I may be wrong about this, but I think we were both wanting a traditional proposal and thought of it more as a fun way to celebrate the milestone than a formality making it official. That said, if it had seemed like Drew wanted to get married but had no interest in a traditional proposal or whatever, I’d have just said, “Fine. Let’s set a date,” and we’d be engaged. Maybe not as “fun” (for us), but we’d still be on the road to marriage, and isn’t that the whole point?

Anyway, I get so many letters and see so many forum threads about women feeling completely frustrated with waiting for their boyfriends to propose (and I’m using heteronormative terms here because it is almost exclusively in straight couples where I see this issue). Is it really a proposal they’re waiting for, or is it an agreement to get married? They’re different things, after all. I feel that, if your guy isn’t willing to even discuss a timeline for marriage and you are ready, like, yesterday to walk down the aisle, then maybe you two are at different places and it’s time to move on. Or, you decide how much longer you’re willing to wait — a month, three months, six months max — and move on if the discussion hasn’t progressed at all.

But if you’re both in agreement and it’s just a proposal that’s standing in the way of making it official, why not just do the proposing yourself? Or, say, “Hey, let’s be engaged now!” And then you’re engaged. Maybe that’s not as fun and festive, but, if the waiting, waiting, waiting is really driving you nuts, cut it out. Take some ownership of the situation and make yourself a fiancée. And if you need a ring to make it feel real, here are some more non-traditional ones that I love, ranging from the price of a movie ticket and milk duds to the price of a new Nissan:

1.55ctw Emerald & Diamond Ring • $2,495.00

KALAN by Suzanne Kalan White Topaz & 14K Yellow Gold Ring • Suzanne Kalan • $462.00

Ippolita 18k Rock Candy London Blue Topaz Ring • Ippolita • $1,395.00

Monique Péan Diamond & Fossilized Woolly Mammoth Ring • $2,345.00

Janna Conner Fine Jewelry Petite Diamond Ring • Janna Conner • $220.00

Monique P?an Diamond Slice Ring with Triangular Diamonds • $14,160.00

Aurora by EFFY Opal (1-3/8 ct. t.w.) and Diamond (1/4 ct. t.w.) Oval Ring in 14k Rose Gold • $1,199.00

Ceylon Sapphire Gold Twig Solitaire • Michelle Oh • $783.00

Skyline Silver Pave Style Round Cut Ring • $24.99

MP Mineraux Rose-Cut Black Diamond & Platinum Ring • Black Diamond • $13,090.00

city x city Pure Silver-Plated Cubic Zirconia Vintage Engagement Ring • jcpenney • $42.00