Question: So I've been frisky with a friend...

So I've been frisky with a friend on-and-off for two years. We both tend to disconnect. However, recently we've been pretty connected - long phone calls, lots of text messages and when he comes over, he hangs out for a while. The sex has been a bit more intimate, too. I want to say I'm growing feelings for him, but I don't know where he stands. I tried giving him hints, but I'm not sure if he's getting them. How do I ask him what he feels and what he wants?

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From the Expert, Jenn Clark:

Ah, yes - the booty call that you hope will turn into something more. It’s a common enough tale given the current frequency of no-strings-attached sex and friends with benefits-types of relationships. I receive many, many questions just like yours and it’s not surprising to me that they are always written by a woman. Why? Because men don’t attach emotionally as a result of sex. Yet, women? Well, we’re often a different story, aren’t we?

Your situation is one reason why I am not an advocate of the booty call, especially with a man who you could potentially want as a boyfriend. Even though you may start out a casual relationship thinking “it’s just sex,” it’s actually quite typical that you will eventually want more. What sucks is that by that time, the boundaries of your relationship have already been defined. And the terms are usually much better for the guy than for the girl. Think about it: He’s getting sex without having to do all of the “boyfriend activities” that would normally be expected of him. He doesn’t have to maintain regular contact with you, he doesn’t have to take you out on dates and he can see other women if and when he feels like it. Meanwhile, the longer this situation continues, the higher the chance the woman involved will begin to have real feelings for him. But why in the world would the guy be inclined to change the nature of the relationship given the fact that he’s pretty much getting his cake and eating it, too? This is why booty calls don’t usually turn into relationships.

You wrote that you “want to say” you have deeper feelings for him. Alright, sweetheart, in order to tackle your situation the first thing you need to do is get real. You absolutely, 100% have feelings for him! If you didn’t, I highly doubt you’d take the time to “drop hints,” worry over how he feels about you or -- let’s face it -- bother to write this question. You really like him and you want more than a casual thing, and it’s time to admit it. This is an important thing to do, because you have to get honest with yourself about what terms and conditions of the relationship will work for you going forward.

Let’s break this down. If he’s unwilling or unable to give you more than you’re getting now, it would be a terrible thing for you to continue in this relationship as-
is. In fact, you will most likely get incredibly hurt. So if I were you, I would make up your mind right now that if your feelings aren’t reciprocated, it’s time to end
the sexual aspect of your relationship with him. Further, continuing in this arrangement won’t make him more likely to eventually develop feelings for you. In fact, it will have the opposite effect.

So what should you do right now? Given how you feel, I think you have only one choice -- and that is to honestly tell him the truth. Dropping hints or dancing around the subject aren’t going to do you any good. It’s time to be transparent and open. I’d further suggest you do this at a “sex neutral” place and time. This means you don’t tell him right after you’ve gotten “frisky” (to use your terminology) or in the comfort of your bedroom. Don’t invite him over late night (causing him to think he’s about to get some) and then blindside him with the news. Instead, why not try meeting him at a restaurant or park? Or ask him to meet you for a coffee during the day.

When you do talk to him about this, be direct. Explain that you have always valued his friendship and enjoyed his company. And then let him know your feelings have grown deeper and you’re open to something more with him. Personally, I wouldn’t put him on the spot to tell you how he feels about you. Simply hear to what he has to say in response. In fact, you’ll get a much better sense of exactly how he feels if you don’t ask him directly and instead listen to what he says. If it doesn’t seem like your feelings are reciprocated, thank him for his honesty. And then stop sleeping with him! If he does, congratulations! You’ve managed to transform an FWB-situation into a possible relationship. No easy feat, my friend.

It could be that your longer conversations, time together and more intimate sex are indicators that his feelings have grown as well. Or it could be that he’s simply comfortable with you and enjoys your company and yet has no intention of having a serious relationship. Either way, it shouldn’t be seen as a reflection on your value or worth. The truth is that men treat us in the way we require them to treat us. When we agree to no-strings-attached sex, the vast majority of men won’t be too eager to start attaching strings afterward. So if it doesn’t work out with this guy, do yourself a favor going forward. Don’t get involved in a casual sex relationship unless you know with a million percent certainty that you will never want anything more.

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Jenn Clark is a relationship advice expert and author of the book “How to Be a Goddess (A Step-by-Step Guide to Becoming the Woman Men Dream About…).” You can find it on her Facebook page: www.facebook.com/jennx30somethingandsingle
Or on amazon.com at the following link: http://www.amazon.com/Goddess-Step--Becoming-About-ebook/dp/B006HBSWSS/r

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