[anonymous5386]

Ok, I dare think that even my knack for finding myself in odd, over the top circumstances with dating is having its envelope pushed at the moment. Where to begin? I’ve taken on a new roommate, we’ll call her Stephanie, who works with my other roommate, we’ll call her Vanessa.

Stephanie is new to New York from Michigan and really trying to make it out on her own. She had a rough upbringing with foster care and such, and hasn’t known much stability. She has the most wonderful, sweet, life-loving personality that in a short time has given me confidence to do things I hadn’t dared do before and so far, no regrets! 😀

We met briefly in a store at the check-out line, I was bumming it in my lazy Sunday best, basketball shorts and a white tee undershirt. I wasn’t going to say anything to her as she caught my eye immediately, but my roommate Vanessa that I was picking up from work came in and Stephanie called her over. Vanessa introduced but then later on explained Stephanie had moved out here from Michigan for a guy. I can respect that so I made no further push on the topic, I didn’t know her well anyways.

I had lunch in Stephanie’s restaurant one day as I was in town on business. Shared a few jokes and all was well.

Last Wednesday, Stephanie called Vanessa asking to hang out. I thought I’d tag along as I had nothing more to do and we all went to a local tiki bar on the water. Now, we were really just getting to know each other for the first time that night, but not 10 minutes into the drive it felt as if we’d known each other for years and were just getting reacquainted. Later, Stephanie was explaining she was looking for a new place to live as issues were arising between her and her boyfriend and his family. She expanded that she would REALLY like to move in with us if she could. She listed a bunch of pro’s and I questioned her a bit, but everything was sounding great.

At some point, a guy she knew, not her boyfriend, came by the bar and started hanging out with us. I could tell immediately that he was interested in Stephanie, more so physically than anything else. Typical badboy guido. I didn’t say much towards him but a couple things that stood out between Stephanie and myself that night, she elected to carving our names into the wooden dock railing. Hers, then mine, then after a remark from my roommate Vanessa she added that name, never the other guys name. “Cool,” I thought. The other big thing that took place was during a private conversation between us in which she explained she was unhappy with how she rushes into everything, “I rushed to New York, I rushed into things with my boyfriend, and then I met this guy, and then I met you…” and she left it there at that. [color=#008000]First thing I’d like advice on what in the world she meant by that, and how far I should read into it[/color]

The next day, we spoke via Facebook, made plans to go to a parade and a pub, I blew off a Yankees/Mets Subway Series game, explaining to my roommate Vanessa’s sister that “I gotta see ’bout a girl” (Good Will Hunting style). We had a wonderful time at the local dam where I picked her up, hiked a bit, took in the sights, talked and reflected on the night before. Took her back to my apartment to change before the parade and to let her see the place as we had decided to give her the chance to have a few “trial sleepovers” before deciding to let her move in. And we wound up cuddling on my papasan couch and dozing off for a bit. The parade was fun, she was introduced to a number of my old business clients in the town, we had a few drinks and stopped over for sushi.

We went back to my place to surprise my roommate Vanessa and began plotting a prank on her. The biggest sellers were sexual in nature, and so research began on how she could best “fake moan.” Then we began cuddling and watching pornography together. Something I’d never ventured to do. She’d already expressed a surprising level of comfort with me. Fast forward a few days, she spends Friday night over, we get inebriated, start sharing personal stories, she’s massaging my back all the while. In the morning, she’s decided to break it off with her boyfriend. I decided that she could move in. She got in around 4:15am Sunday while I was passed out but I’d left the keys for her. Slept for 3 hours before we had to go to work, I drop her off and she doesn’t come back home for about 3 days. We talk via phone all the while, but she’s been staying over with other guy friends. (I don’t know the validity of it but I trust she’s not an easy hook-up because I know my game and I know it well, she deflected my best routine with ease that has never been deflected before and no, I will not share it.)

Anyways, since we met, there’s been constant flirting, I have seen her naked, it’s been like a week, there’s constant talk of cuddling and her talking of where we’ll go for our first date, etc. etc. I’m trying with great difficulty to resist her advances because I don’t want her to feel awkward in her new home, and be forced to move back to Michigan before she even has a chance to make it in New York. I’ve tried explaining I feel like I could see her as a little sister type to protect (bullsquat) and I’ve tried reminding her that as roommates we shouldn’t do anything, to which she responds, “It’s only awkward if you make it awkward”. She introduces me to friends of hers at work which already feel like they know me based on all they’ve heard. I’m planning on inviting her to my cousins wedding next month. I’M TOTALLY LOST. Is she sleeping with these guys? Is she deflecting them? Are they just rebounds? Is there genuine interest from her to me?

PLEASE HELP!

[AskApril Masini]

How old are you? Are you male or female? How old are the women?

Let me know, and I’ll answer your questions! 😀

[anonymous5386]

I’m male, 26, Stephanie, the new roommate is 21, and my other roommate, Vanessa, is 25

[AskApril Masini]

Got it! Thank you. 🙂

So, before I answer your specific questions, I’m going to address the elephant in the room:

If you choose female roommates, you’re creating chaos. Men and women who live together will develop feelings for each other, and they won’t always be at the same time. This makes having a roommate fraught with problems. For instance, if you take on a roommate, date her, then decide to move on and date others (or vice versa), she’s going to be one unhappy roommate. The complications that arise from that scenario can get ugly, fast. So, my advice is to have male roommates and date these women outside of a roommate situation. Your life will be a lot happier and healthier.

As for your questions, here goes!

[quote]The other big thing that took place was during a private conversation between us in which she explained she was unhappy with how she rushes into everything, “I rushed to New York, I rushed into things with my boyfriend, and then I met this guy, and then I met you…” and she left it there at that. First thing I’d like advice on what in the world she meant by that, and how far I should read into it[/quote]

You shouldn’t read into it at all. She’s being honest with you that she has a tendency to rush into things. She’s rushing into a roommate situation with you, and she’s telling you that when she rushes into things, she makes mistakes. Knowing this, it doesn’t sound like she’s roommate material, but if you do decide to take her on as a roommate against my advice, you should have a good lease agreement with her and make sure to take a security deposit that can be used in case she breaks the lease and moves out early.

[quote] Is she sleeping with these guys?[/quote]

Maybe. It sounds like she’s playing the field, and you’re a potential part of the field.

[quote]Is she deflecting them? [/quote]

Maybe. Again, it sounds like she’s newly single and playing the field. You already have experience with her that’s outside the guise of normal roommate or potential roommate experience — you’ve seen her naked, given massages, watched porn together — without dating her. You know how she operates, so you should expect that she’s doing the same elsewhere.

[quote]Are they just rebounds? [/quote]

Maybe. But it’s normal to want to date and play the field after getting out of a long-term relationship, which it sounds like is where she’s at. On the other hand, it doesn’t sound like she’s got a new boyfriend to replace the old one, so rather than these other guys being “rebounds” it sounds like she’s just playing the field and these guys are just men she’d consider a relationship with, and is maybe doing so right now.

[quote]Is there genuine interest from her to me? [/quote]

I’m not sure what you mean by genuine interest. Clearly, she likes you enough to hang out with you, drink, watch porn, give massages and get naked. But since you haven’t asked her out on a date, or tried to pursue her as a romantic interest, it isn’t clear that she’s being given something to be interested in. 😉 You’re also sending her mixed messages by considering her as a roommate, but then watching porn with her and considering asking her out on a date. If you’re a little more clear on what you want, it gives her an opportunity to be clear back.

Often, when people write me here because they’re confused about someone — the reality that they have trouble seeing is that they’re the ones who are sending mixed and confusing messages. When you get clear and focused, so does the world. 🙂

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