Dear Wendy: “Should I Pursue A Long-Distance Relationship Or Move On Already?”

I have been talking to this guy for a few months now. We were good friends in college and reconnected via Facebook and upgraded our flirtatious banter to texting and phone calls. He lives about four hours away from me (I realize this is not really that long distance considering you moved across the country for a guy). We have each visited each other once in the last two months. Both of us have spoken candidly about wanting to date but it’s always under the pretext of “if you lived here.” He’s asked me to move in with him numerous times, and while I know I wouldn’t do that on a whim, I would be willing to do long-distance for a little while to see how compatible we are and then in, like, a year revisit the idea of moving. Should I give up and move on? Or should I try to talk to him about it? I can’t imagine losing anything by telling him how I feel, even if he says absolutely no to long-distance, then I’ll know for sure that we should stop talking, right? – Feeling Lost

It’s obvious you’re both interested in each other and want to date each other and this whole “if you lived here” nonsense is just BS because you’re both too chicken to be the first to say, “Hey, let’s try this out and see what happens!” But, time’s a wastin’, darlin’, and if neither of you makes a move soon and cements this thing as an actual real relationship you’re giving a shot, you’re both going to get bored and move on. Or, you might just stay in this awkward limbo land for a really long time with nothing really happening, which would be equally frustrating.

So, quit waiting around and tell this guy you’re willing to give your relationship a real shot if he’s into it. Discuss what you both would need from the relationship — how often you’d like to see each other (and how often it’s possible to see each other), whether you’ll be monogamous or not, and if either of you would be willing to move eventually if your relationship got to that point (if the answer is straight-up no on that one, you might has well move on now because it ain’t gonna work). If you know you’ve got nothing to lose if you talk to your guy about a relationship, why not give it a go? It seems silly to walk away from a potentially satisfying relationship when you both seem to really like each other just because you’re scared of being rejected or things not working out. As I’ve said before, if you’re with the right person and you’re both committed to making it work, there’s no reason an LDR can’t be successful. I count my marriage as just one of many examples of this truth.

I’ve lived in New York City for a few years now, but after a stressful year and a drawn-out breakup, I decided to move back to Florida in August to live with my parents for a few months and get my life back together. Right after I left, one of my best friends in NYC moved in with a group of guys she met on Craigslist who were trying to find a subletter. I just moved back about a month ago, and ended up hitting it off with one of her roommates after we all went out drinking one night. I really like her roommate, and I think it could be the start of something serious. The only problem is my friend.

At the onset, she told me she thought we would be cute together and even encouraged me to make a move. She has since changed her mind. She told me outright that she doesn’t like it — that she doesn’t want me to choose hanging out with him over her and that if I’m at her apartment, she wants it to be because of me. I’m trying to figure out what to do; if the situation were reversed, I feel like I would be overjoyed that I’d see her even more. She’s also over at her boyfriend’s apartment a lot so she isn’t home a lot of the time. And I know she doesn’t secretly like him because she has a crush on her other roommate. We’ve talked about it a few times, and each time I tell her that if she wants me to stop, I’ll do it. But she tells me she doesn’t want me to stop seeing him if I don’t want to, just that she’s unhappy about it.

I never expected to choose a guy over a friend, but I guess I just can’t see the issue here, and I think a really great relationship might be a possibility. However, I don’t know what to do about my friend, because if she’s not happy about it I have a feeling it’s going to ruin whatever might come out of this. Help! — Crushing on Friend’s Roomie

Unless she knows something unsavory about her roommate and is trying to protect you from him, your friend is being totally juvenile. But before you blow her off, give her the benefit of the doubt and ask her outright if she knows something about him that would change your opinion about pursuing him. If she doesn’t, then you need to tell her that you’ve given it some thought and you won’t stop dating him — that you really like him and you want to see if there’s relationship potential for the two of you. If she has a problem with that, she needs to deal with it on her own, but don’t let it affect your behavior. She clearly has issues that have nothing to do with you. Might you lose her friendship if you continue dating someone she doesn’t want you to date? Maybe. But do you really want to continue being friends with someone who thinks she has a right to manage your love life?

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