DEAR DR. NERDLOVE: I have a situation that I don’t really know how to handle.

A little backstory; I’m 30 year old woman and I’ve never been in a relationship. I’ve been complimented on both my looks and personality, but I’m an introvert and have struggled with self-esteem and anxiety issues most of my life so I don’t meet people often and rarely put myself out there. This means I have pretty much no experience to work from when it comes to relationships. But despite anxiety issues, whenever I like a guy, I do tell him, and every time I’ve been rejected and we just stayed friends. I have had guys like me, but please believe me when I say they have all been creeps, ranging from making me feel like they’re trying to buy me (I am neither a hooker nor something in a store for you to check the specs on and then haggle a price for. Please don’t treat me that way) to full-blown ‘I know where you live’ stalking. These two facts combined have not helped my unwillingness to put myself out there. But last year I moved to a new country where I didn’t know anyone and I wanted to make some friends, so I put myself out there and met a guy who I became good friends with. I developed a crush after a while, was rejected, and we just stayed friends. Again. He’s a pretty awesome friend though so it didn’t really bother me that much.

Months after my confession, we were out at a bar near his place, and one thing lead to another. Neither of us were even close to drunk (nothing happened until a couple of hours after we’d had a single glass of wine) and neither of us was unhappy that it happened or regretted it in any way, and after a few long and awkward conversations we decided to be FWB. He’s ridiculously comfortable talking about feelings and really good at knowing when I’m feeling uncomfortable so he’s pretty easy to talk to. He knows when to push me and when to lighten the mood, so we have been able to discuss it pretty well and made sure we were both on the same page and comfortable with that.

That went on for a few months. Things were going well. He’s helped me open up more emotionally and keeps trying to help me with my self esteem issues. I’ve been getting a little better about all that and I’ve gotten a lot more relaxed around him because of a combination of the above, and KNOWING where I stand with him so I don’t have that anxiety of ‘what if?!’. Then things started changing… And this is what I need help with. I think he’s starting to view me more as a girlfriend rather than just a friend. But I’m not sure if that’s just me being hopeful and wanting that, or if it’s actually happening. And despite his openness to these types of conversations, I don’t even know how to START having that conversation.

Anyway, there are a few things that have made me think things are changing on his end. He’s not a big texter. He prefers to talk in person so most of our texts are arranging a when/where/what of the next time we hang out. He’s like this with everyone, not just me. He doesn’t even have his phone on him when he’s doing a lot of things, and when he does have it on him, it’s turned off a lot. But he’s started texting me more often, and for unimportant things. Just to make a joke, or tell me something that normally would have waited till we hung out in person. And making arrangements with me further out as well. He’s started making more time for me, and I was already the friend he saw most often. He’s started introducing me to more of his other friends (I’d already met some, they’re all lovely people), and bringing me along when he’s seeing them. He’s joked about introducing me to his parents. He made a point of telling me he wanted to spend time with just me for his birthday. He’s started using pet names when he talks to me like ‘sweetie’…

Typing all of that out I feel like an idiot for thinking I need external confirmation that things have changed. But I still don’t know what to DO with that information. How do I approach starting that conversation? A part of me is still scared I’m just seeing what I want to see. But if things ARE changing, and it’s because I’ve been getting more comfortable with him and more ‘myself’ around him, so to speak, the anxiety of not knowing could reverse that so I SHOULD have the conversation rather than letting it fester in my brain like I have been… I just can’t figure out how to bring it up! How do I say ‘hey, I know you’ve already told me you don’t feel that way for me, but, do you feel that way for me?’ It sounds ridiculous!

Please help me before I do something stupid…

Trying To Exit The Friend (With Benefits) Zone

DEAR TRYING TO EXIT THE FRIEND (WITH BENEFITS) ZONE: Sometimes you have to take somebody’s behavior at face value, TEFWBZ.

Here’s one of the truths about FWB relationships: they all end eventually. Either you quit having the benefits (y’know… the banging) or you quit being friends.

Now, as scary as that last one sounds, it’s not automatically bad. Sometimes the “quit being friends” part means that the friendship ends, rather like a break-up. However, other times, it means that your relationship evolves into something more intimate and committed than a simple “we like to bang on occasion.”

As a general, when you’re maintaining a casual relationship, you keep your partner at a certain distance. You don’t treat them casually or cruelly, but you simply aren’t as emotionally intimate as you might be with someone you were fostering a deeper relationship with. People who want to keep a relationship strictly sexual tend to go out of their way to avoid setting up a dating frame – you don’t have the same conversations you might have with a friend or partner. You don’t necessarily integrate them into your social circle. You almost never make plans for things further ahead than the next time you’re gonna hook up.

But hey, guess what your honeybun is doing? He’s doing ALL those things. Cute nicknames, introducing you to his friends and family, wanting to spend special time with you on his birthday… those are typically the signs of someone who wants more than just a casual fling. He is, in short, acting like someone who’s caught feelings and wants to act on those feelings.

Now, he may be doing it consciously in hopes that you’ll get the hint – some people feel like they can’t or aren’t supposed to walk back the declared “we’re just f—king” status. Or it may be somewhat unconscious. He may not realize how things are changing and that he’s giving off more relationship vibes and this is an indication of how he feels without realizing it.

But there’s only one way to know for sure what’s going on: you just ask him.

It doesn’t have to be a big deal; not every DTR conversation needs to be dramatic. The next time you two are hanging out in person, just mention “hey, am I crazy or have things been getting a little different between us? I mean, I really like it, but I want to know if I’m picking up on something or not.” This gives him some space to either say “yeah, actually, I think you are” or “No not really” and lets you both agree to let the status quo continue.

But if you want to know, then you’re going to have to be willing to risk things and call the question. There’s no reward without risk… but this sounds a lot like a sure thing to me.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: Okay, so I have a situation where I got involved with a girl who’s last relationship was abusive (emotionally and physically). We’d both just moved into college (neither of us is a freshman), off campus, second night we hooked up. That night, when we talked, she seemed very interested in making it into something. Maybe not make it really serious, but at least attempt dating. We were working together when we met, for the school, so during the day we obviously kept everything under wraps.

Two days later I asked if I could see her again that night, she said yes. A few hours later I get a text saying we should just stay friends. I’m totally cool with this, she is making her wishes clear and I told her we could stay friends.

The next day we drink with some friends. She tries to hook up with my best friend when everyone is gone. They kiss for 5 seconds and he gets uncomfortable and backs off. I knew about it, but I didn’t care and didn’t make a big deal over it, I’m not the jealous type.

The next day we are hanging out with a bunch of people, eating lunch, and she sends me another text saying she regrets what she said the previous night. I’m a little exasperated at this point, but I tell her we should talk about it later, in person. At this point I didn’t really know about the abuse. That night I walk her home, we talk, she explains her history. Eventually we decide to try dating. I leave thinking that we are on the same page.

The next night she changes her mind again. My response is calm, but I make the mistake of asking her if I can ask her out in the future once we’ve both figured things out. I feel like this could have come off as needy. But she says of course I can, and we leave it at that.

Finally, a week later, after continuing to remain friends, she wants me back again. We talk, I tell her I’m pretty cautious at this point and I don’t want it to be more of a mess. But she seems really sincere, so I decide to give it one more try. We decide on a date for two days later. A few hours before the date she cancels, says we need to stay friends.

Finally at this point I just said I was done. I’m not mad or hurt, I’m just done with this mess. She apologizes profusely and I basically just tell her I won’t hold a grudge because she’s had a rough year and I won’t hold it against her. But I ask her to please treat people as she wants to be treated. She wants to stay friends.

I guess my question is what could I have done differently? I realize I should have walked away sooner, but this girl is amazing. Ambitious, smart, works really hard (full ride student), and very pretty. The pathetic part is, if in 6 months she changed her mind again I might be willing to try it. It’s not that I’ll wait, I’m pretty confident and I try to go up to random people and meet them several times a week. I just haven’t met anyone I care about more than her, yet.

I learned a lot from this, but I feel like I could learn more if someone else took a look at it.

– Exasperated & Confused

DEAR EXASPERATED & CONFUSED: I’m going to be blunt: what you should’ve done is cut things off a lot sooner, E&C. This was never going to go anywhere. I’m sure that she’s amazing as hell and cartoon birds do her hair in the morning when she gets up, but the fact of the matter is that she was jerking you around.

Now to be clear: it is absolutely awful that she had a s--tty relationship before you got together. She was abused, and that frequently leaves scars. I completely empathize with her over that and hope she gets help because she seems to still be in pain from it. But while the abuse (potentially) explains her actions, it doesn’t excuse them. It would be one thing if she had said “look, I can’t deal with things right now, I’m not in a good place, emotionally, to date, I’m sorry.” But unfortunately, she didn’t.

It’s good that she apologized, which is a solid start. But the truth is that, intentionally or not, her behavior was negatively affecting other people and that’s not cool.

Here’s a truth about dating, E&C: when you date, you open yourself up to the possibility of getting hurt. There are manipulators and users, toxic people and abusers, and there are people who’ll keep dangling themselves on a string to keep you interested but yank it away just as you’re about to reach it. Some may be malicious, some may just be clueless and some may be flailing around trying to figure things out… but it still ends up hurting people on the receiving end.

The way that you keep the toxic people out of your life is developing and maintaining strong boundaries. In the case of this on-again, off-again girl, you were putting up with behavior over and over again that was leaving you confused and upset. That’s a time where you have to have boundaries. Yes, you need boundaries, even with people you care about or who aren’t acting maliciously.

In an ideal world, you would have called things off earlier would. You could have said “Listen, I like you and I think you’re amazing, but I can’t put up with this. You’re going hot and cold on me and it’s confusing, it’s hurtful and I can never know where we stand or what’s happening between us. I don’t know what’s going on and I hope you’re ok, but I can’t keep doing this, and if we’re going to keep doing this dance, then I have to step away.” Then you wait for her response. If she pulled the same behavior again, then you should’ve said “Look, I said I can’t keep doing this.” and walked away. This isn’t how someone treats a friend, never mind how someone treats a potential lover.

The other thing you need to realize: unless she changes her behavior — whether that means getting help that she needs or growing and maturing — then there’s no point in speculating about what might have been or what could still be. She doesn’t sound like she’s in a place to date right now. And yeah, I’m not surprised you’re still hung up on her. I get it. You’re young and unless I miss my guess, this was your first major relationship. But here’s the thing you need to keep in mind: there are other multitudes of women out there who are just as hot and ambitious and smart if not more so. More importantly, there are other hot, ambitious, smart and hardworking women out there who are in a better place emotionally and who won’t make trying to date such a roll of the dice.

My advice? Go out. Date around. Meet other women. Learn how to develop and maintain your boundaries. You can maintain a friendship with her — assuming that she doesn’t keep blowing hot and cold — and date someone who is ready and able to be in a relationship with you.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE:

I have been seeing this guy online for a good 8 months or so. He’s very supportive, kind, silly, sexy, and he doesn’t judge me for having not the best past. We’ve been there for each other, and we’ve helped each other grow a bit. The problem is, we are currently just online FWB.

I’m not so sure I want to be FWB anymore. He knows I care very deeply for him, but hasn’t really given me a response to his feelings for me. He’s been giving me huge mixed signals. One night he told me he prefers to be friends, the next day he tells me he was thinking of me a lot in the hospital, and how he wants to hold my hand and other sweet things like that. I don’t know what to do. I don’t want to be the girl in “Paradise by the Dashboard Light” and give him a pressuring ultimatum, but I really love him and can’t stand the thought of being an ego boost.

Do I confront him? How? 

Love,

Reading Foggy Tea Leaves

DEAR READING FOGGY TEA LEAVES: Dump his ass.

Sorry. I realize that’s harsh, but he’s straight up jerking you around.

He may be a sweet, supportive guy, but he’s treating you like shit. You and he want entirely different things. You want an actual relationship with everything that means. He wants continuing access to your vagina without actually committing. This is why he’s giving you mixed signals and blows hot and cold; he wants to be friends but he also knows that if he doesn’t keep dangling the relationship carrot in front of you, he’s going to be left alone with his stick. As soon as he said “let’s just be friends” he realized that it was a toe over the line and tried to pull you back in by being all lovey-dovey. He’s taking advantage of the fact that you care for him more than he cares for you and unless you take a stand, that’s all that’s going to happen.

You deserve better than this.

You can give him a heads-up: either you get an answer or you bail… but I’m guessing we both already know what that answer’s going to be.

Drop him like fifth period Calculus and find a dude who is actually in tune with what you want and isn’t going to play games with your emotions.

DEAR DR. NERDLOVE: I recently decided to start looking for a long term relationship, but not for reasons most do: not for the need of love or even a connection to others or a fear of ending up alone. I’m perfectly content with being by myself — I often prefer it. Instead, I’m looking for financial reasons: as in two people paying bills, rent, etc. is cheaper than one.

Now a little bit about myself: I’m a 29 year old guy, I’ve been in a few long term relationships, but I knew it wasn’t really my thing. I stayed in my longest relationship because my life at home was falling apart, and leaning on others was easier than dealing with my situation. After a few relationships, I made the choice of not seeking that in life, but more of short term engagements when I was feeling the need to be with someone. I don’t really need sex or emotional connections; I do enjoy it from time to time but I can long stretches without it. The problem I find  is that as enjoyable as meeting new people is, learning interesting things about them is for lack of a better term… boring. I get bored of people, and when that happens I tend to just end things and move forward with my life until I meet someone who interests me again.

Now I recently went through life changing events. My father passed away over a year ago, and as most do when something that big happens, I took some time to self reflect and see if changes needed to be made. 

These days, I’m in a good place emotionally, which leads me to my wanting to find a long term partner. I have discussed it with some close friends and a few coworkers whose opinions I find often have value and for the most part I keep being told it’s wrong. I’m willing to be all the things that make a good partner for whoever, I just don’t need most of them myself and I’m fine with that. However, I still get told that what I’m doing is bad.  I feel everyone enters into a relationship for their own reasons; this just happens to be the reason I’m looking for one.

Was just looking for the thoughts from someone whose column I enjoy reading

Got To Be In It To Win It

DEAR GOT TO BE IN IT TO WIN IT: Your friends are right, GTBITWI: that’s a shitty reason to be in a relationship with someone.

Your issue here isn’t your motivation, it’s what you’re looking for. If all you’re looking for is someone to split the bills, then you aren’t looking for a romantic relationship, you’re looking for a roommate. 

This is all about expectations and connection. People who are looking for relationships are looking for someone to share their lives with, someone that they have a connection to and to be intimate with — emotionally as well as physically. It doesn’t matter that you’re willing to play the role of “boyfriend” in order to find someone to help you live more frugally; people don’t want someone who’s acting like a caring and attentive partner, they want the real thing. What you’re doing is, at best, offering a sort of long-term “boyfriend experience” in exchange for someone splitting half the rent and utilities. Frankly, unless that’s how you’re actually presenting yourself to people — which sounds more like some form of being a sugar baby, rather than a partner — then all you’re doing is setting them up for disappointment and, likely, heartbreak when you inevitably get bored again.

Do yourself a favor: get off the dating apps and get on Craigslist instead. Find a roommate to split an apartment with and let the folks who are sincerely looking for relationships alone.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com