Ask Jess
Dear Jess,
I have a problem that might be pretty common – because it seems like all my friends have had this problem as well. There’s a guy in my life who I just CANNOT FIGURE OUT. I guess he’s the Prospect I’m Not Sure Is A Prospect in my dah. That is, if he’s even in my dah. Sometimes I’m not sure. It’s all very hot and cold.
Six months ago, I took a night class in Italian and met him there. A group from the class became friendly and started going out for drinks, and I always thought he was pretty cute, but it wasn’t until we started Facebook messaging about some funny class photos that I thought our friendship (or whatever) might branch out from the group.
Also, I think we almost made out one night after class – the vibe was there, unless I’m crazy – but then we got interrupted and never really mentioned it again.
And now…I don’t know. We’ve never hung out one-on-one, but we have fun together in group settings. We also text and Gchat pretty regularly – but his tone is inconsistent. One day he’ll be texting me and seem really enthusiastic, and then a week later, I’ll text him and he’ll barely get back to me. Sometimes he casually brings up things we should do together – try out a new restaurant, watch a baseball game – but then he rarely follows up, which annoys me. Yet since we haven’t hooked up or “dated,” it doesn’t necessarily feel like he’s blowing me off. It just feels like I’m in this weird no man’s land of his dah.
What am I supposed to do here? How can I insert myself into his dah without seeming desperate or pushy? Or is it just a lost cause? I kinda like him. If there’s a shot to be had, I’d like to take that shot.
Sincerely,
Mixed and Muddled Millie
With a puppy.
Here’s a special Ask Jess column to ponder as we roll into the weekend! A query from a confused, world-weary boy.
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Hey Jess,
I just tricked a Hot Sex Prospect – who was also a Girl Who Just Blew Me Off like three years ago – into going out with me tonight. How should I proceed?
Remember you’re advising an idiot, so please simplify things for me.
Thanks!
Idiot With A Second Chance To Score
Dear Jess,
I have been sleeping with this guy for about six weeks. First it was casual, but now, it’s five or six nights a week. He spends the night at my place almost every night, and also hangs out during the day for hours at a time.
We still have never gone on a date or met each other’s friends, but I’m starting to think this could go somewhere. Casual sex is one thing, but spending all your free time together is another – and it’s obvious that we’re genuinely enjoying each other’s company.
I should mention, though, that immediately at the beginning, he made it clear that it was just sex, and claimed that we didn’t have a “relationship connection.” At the time, I was cool with that. He’s not the type of guy I usually date, and I thought we’d just have fun for a while and then go our separate ways. But instead of our connection fizzling, it feels like it’s gotten stronger with time. The more we hang out, the better it gets.
But, he did say that. I can’t ignore it.
The truth is, I’d like to at least try dating him. Whatever that means. Is there any hope for this to become more? What should I do?
Thanks,
Sexing in San Antonio
“We all get into romantic ruts sometimes. Maybe we’re busy working hard, or we’re traveling a lot, or it just seems like we happen to be circulating in the same crowd and spending all of our time with the same people. Honestly, whose love life couldn’t use a little nudge in a more exciting direction?… …Here are 10 tips for boosting your dah and getting some of those ambiguous – but fun and intriguing and promising – connections going. Today, right away, immediately.” READ MORE of Jess’s advice at The Frisky
Dear Jess,
My last three girlfriends all complained that I didn’t criticize them enough. I know…what?!
I wasn’t sure what to make of that, but they all ended up dumping me because they felt they “weren’t being fair to me” – as though I was somehow putting up with them against my better judgment. The truth is that I’m just really laid back and rarely get bothered by stuff, so I’m not inclined to be critical often.
I would have thought this would be a Good Thing, but now I’m starting to wonder if I’d be better off being crankier and more judgmental, no matter how counter-intuitive that notion sounds. What do you think?
Love,
Too Chill For My Own Good
______
Dear Jess,
For the past month, I’ve been talking to, hooking up with and going on dates and/or non-dates with a guy who I went to school with. He’s really funny and sweet, and I love talking to him and being around him.
My issue: I just got out of a two-and-a-half-year relationship where I always put my boyfriend first. I am finally enjoying focusing on myself and spending time with my family and friends. I feel independent, and I couldn’t be happier.
Yet this guy asks me to hang out multiple times a week, and I find myself making excuses. He is starting to get a little possessive, and he gets upset whenever I don’t want to hang out. He really is sweet, and I can tell that he’s starting to like me. But it’s moving very fast for me. I really like him, but I am not ready to be someone’s girlfriend again (yet).
How do I ask him to slow things down without hurting his feelings or making him think that I’m not interested in him?
Love,
Girl Who Needs A Boy Detox
Dear Jess,
I love reading your site. Dating & Hookup, Non-Dates, Techno-Romance…they all sound so fun! And I think they’re very real, because I see my friends dealing with this stuff all the time.
However, I’m in sort of a different situation. About six months ago, my boyfriend of two years and I broke up. Long story short, we had our issues, but he’s the one who ended it. I really, really loved him, and I ended up being really hurt by how it all went down (he’s already with someone else – OUCH).
Six months later, I’m still not over it. I’ve tried to put myself back out there, and I go out with my friends all the time to meet guys. But once I’m out, I don’t want to be there. All the guys I meet just seem like jerks. And even when I start talking to a guy, I get weird – I freak out if he doesn’t text me back fast enough, or I assume that he only wants to hook up with me and I get upset.
I want to be happy and find a great guy, but I don’t know how to make that happen! Is it me? Is it the guys? Am I doing something wrong? Everyone tells me that time will make things better, but it’s already been SO long and I just want to have fun again.
Love,
Jaded in Texas
Dear Jess,
Here’s the skinny. I started a new job with these two guys who are friends. I really liked Guy A, who flirted with me from the start. But I was working very closely with Guy B.
One night we all hung out, and of course we started drinking. Guy A confessed that he had asked about me and was interested. But then he left the room, and Guy B kissed me (I was surprised!). I pulled back at first, but then I let it happen. I was pretty sure that Guy A saw it.
The next week, things were back to normal – I was still flirting with Guy A, and he was flirting back. In fact, we went out for coffee. Then we all went out for drinks again. And affected by the whiskey, I texted Guy A and said that I liked him a lot. He didn’t text back. Instead, as we all stumbled outside drunk, Guy B tried to kiss me again! And I pulled away. But then we kissed. And I’m almost sure that Guy A saw it again.
I like Guy A so much, in a sincere way. I still catch him staring at me at work, and we have great conversations. But…I fucked things up, huh? Did I miss my chance? How can I show him that I’m interested in him, and that kissing his friend was a mistake???
(And don’t tell me to stop drinking! Because I don’t, which is why the few times I hung out with them, it affected me so much.)
Love,
Mostly Sober Sally
Dear(est Understanding) Jess.
What does a girl have to do to meet men these days?! Or at least, the right men. I am starting to loooooose hope. All of it.
The belief I once had in love, and all its power, has been replaced by bitterness after an endless string of one-night stands and stupid affairs. I can blame it on daddy issues, weight issues, blah blah blah – but really, I’m just stuck. I need and want to start the next phase of my life, yet…
I am 27, I want babies (damn it!), I’ve started my own business and it’s going well, I have great friends and a fun social life, and I even have an amazing shoe collection 
All of it is good. But, my oh my…I’m lonely, and I’m over going through everything alone. I don’t know what to do or where to turn. Men seem to want me for sex, of course, but I don’t want just sex – I want to be taken care of, in the same way that I often take care of everyone else around me.
Help?
Love,
Losing Hope in Lonelyville
Question: How should I handle being single on Valentine’s Day? You know, without feeling lonely or desperate, or convincing myself that I’m destined to become a bitter, self-loathing spinster?
Answer: Read my advice in a new article – 5 Tips for Being Happily Single on Valentine’s Day – that went up today as an Editor’s Pick on Yahoo! Shine and on Tips on Life & Love. No bullshit here, I promise! Just some solid, honest recommendations – some of which came from the trial and error of yours truly…
And then join the conversation on Twitter – #MySingleVDayPlans – and let us know what your plans for the non-big day are!
Dear Jess,
I recently moved to a new city and have been re-building my dah here. So far, so good!
Until last night, when one of the guys in my new dah kissed me. I had been thinking of him as an Ego Booster, and I didn’t really want to kiss him back. But in this weird way, I felt a responsibility to kiss him – like to not return the kiss and give a “let’s just be friends” speech would have been too much of a rejection, and would have made everything seem like too big of a deal. It was just a kiss, right? Not a marriage proposal!
So, we kissed – and then today, he sent me an email apologizing for any “awkwardness” (and for his garlic breath) and inviting me to a concert. Now that we’ve kissed, I know that this would clearly be a date.
How can I keep him as my Ego Booster for now, and transition out of this situation? I’m just not seeing him as a Boyfriend Prospect at the moment – but I also feel like I’m still beginning to get my bearings in this new city, so, who knows, further down the line…? He’s a cool guy, and I’d like to keep him in my dah, if possible.
Sincerely,
New Girl with New dah Problems
Dear Jess,
I’ve been hanging out with this guy – a mutual friend introduced us because we work in the same industry and I was looking to switch jobs, so she thought that he might be able to help me out. We immediately hit it off, and after a few coffees and happy hours, we started making out on a regular basis. He’s really great and has never seemed like a game player. I have high hopes for where this could go.
BUT, something weird is happening. We hung out four times last week, which is way more often than before. And then for three days, he didn’t respond to any of my emails or texts! Nothing! He finally replied to one of my emails a few minutes ago with a short, cute joke, but he didn’t ask me to hang out…
How should I respond? Can I be the one to suggest that we hang out? You know, female empowerment and all that? He’s being strange, but I have trouble believing that he’s suddenly blowing me off or isn’t into me anymore. We were having so much fun!
Love,
Trying Really Hard Not To Be That Stalker Girl