I'm dating-challenged and dropped the ball. How I do pick it back up?
August 26, 2013 7:25 PM   Subscribe

Over last weekend I spent a whole bunch of time with a lovely woman--dinners, picnics, walks, wine under the stars etc. These weren't explicitly dates, but it all seemed pretty romantic. At the end of the evening on Saturday and Sunday we had these awkward pauses when my insecurities and my desire to--give a goodnight kiss? Express my attraction? Or something--were warring. I don't know what she was thinking but it was awkward on both sides. Now I won't see her for a month. Do I email her and explicitly say that I'm interested?

Details and subquestions abound here, but "do I email her?"--and what do I email her?--is the key question.

The background to our long weekend together is that we are both grad students in related disciplines at the same university. We met last year (she's new, I'm within a year, maybe two of finishing my PhD). I was attracted to her, but didn't have much cause to see her and we only ran into each other a couple of times.

Then we both happened to be doing research in the same Faraway Land this month. I'm staying on for a few weeks, but she's headed back to the States. We hung out a couple of times earlier this month, I spent some time helping her with contacts--but weren't in the same town for much time. Then this Friday I suggested hanging out and we ended up spending about twenty hours together between Friday evening and Sunday at about midnight, most of that just the two of us. I initiated every meeting (maybe she's just too polite to turn down invitations? She did once before when she had a prior engagement...) We talked a whole bunch (work, literature, movies, our families, ex-pets, politics, comedy, our backgrounds...), laughed a lot, had some long silent stretches. Not too much awkwardness in the conversation, though. I think. Drinks, a dinner out, a picnic, cooked dinner twice.

Pretty much no physical contact, though. And these were never explicitly dates. And we are future colleagues of sorts in academia (same subregion, similar disciplines) and fellow Home University-ites in a foreign land, so we had other reasons to hang out.

Monday morning she flew back to Home State. Both Saturday and Sunday evenings (fairly late) were capped by awkward goodbyes. I'd walked her back to her lodgings both times and we hung around while I waited for a cab (and for her to let me out of the building--Faraway Land has security issues). I went a bit silent, we made awkward faces and noises at each other at one point, as if to make a joke of the awkwardness (at least, that's what I was doing). All this while I tried desperately to summon some courage to try to kiss her, or say I wanted to, or that this was a date, wasn't it, and WHAT a date!--or something. Then the taxi came and I left. Saturday night it was awkward enough that she actually said maybe she should just go to bed--before she realized she had to stick around to let me out. Gave her a weak hug Sunday night, both nights said I'd really enjoyed myself, she said she had, and we agreed we should hang out more back in Home State.

Um, now what? Her attempt to flee the awkwardness on Saturday seemed like a bad sign, but we went on to hang out for about ten hours the next day--maybe six or seven of those hours on our own. So maybe she thought she'd misread things, too? Or she's almost as bad at this dating thing as I am?

Anyway, I could just keep up a correspondence (something I'm usually terrible about) and try to arrange chances to see her when I get back. But wasn't my failure to stick the landing on these dates (or non-dates?) a big red flag, showing her I'm all inept and sexually/romantically immature?--or convincing her that I'm not interested? Do I need to make clear why I wasn't all suave and self-assured?

Do I email and say something like "Hey, about those awkward goodbyes--I had a really great time and I wanted to tell you that I'm interested. [I don't know how to say this "...you know, THAT way"; "I mean I LIKE like you"--it's like my writing ability has deserted me and left me with the vocabulary of a teenage boy, advice is very welcome] But I just couldn't quite find the way to say it. I hope you felt the same way. Either way I look forward to seeing you more in September." (Except obviously if I misread everything and she doesn't feel the same way, after this email we'd probably both be dying of embarrassment when I see her next.)

So the extra detail that explains why I can't navigate this simple interaction on my own is that I am waaaaay at the far end of the bell curve with dating and sexual experience, for various reasons. I'd say I've had a dry spell, but it's more like Saharan conditions for the past ten years and only one brief relationship before that. I do think it's more about my insecurities than any other universally objectively objectionable thing about me. So I have next to no skills or experience with this kind of thing. I am beanplating obsessively here because I don't know what to do and generally feel like I am sixteen again (except I didn't even attempt to date anyone when I was sixteen), so any advice is welcome.

Also, I'm almost 30 while she's almost 25. This age difference, among other things, had (has) my internal voices of doubt yammering away in overdrive that it would be impossible that she'd find me attractive, that it'd be creepy or pathetic of me to try to date her, etc. I'm also aware that as I've finally pushed myself to try to date after so long, I'm in danger of putting way too much pressure on any given opportunity--and of unloading a decade of insecurities on this unsuspecting woman. And yes, I started therapy just before coming out here and this is something I want to work on. But I won't have an appointment until I'm back in Home State.

So do I need to fret about next steps? Draft that awkward email to explain my prior awkwardness and declare my undying devotion? Just write her regularly until I get a chance to see her--and hope I do better next time?
posted by anonymous to Human Relations (25 answers total) 6 users marked this as a favorite
Email is the worst idea. Why don't you just ask her on a date using the word "date?" You could kiss on that occasion with much less ambiguity.
posted by oceanjesse at 7:33 PM on August 26, 2013 [2 favorites]

Also, I'm almost 30 while she's almost 25. This age difference, among other things, had (has) my internal voices of doubt yammering away in overdrive that it would be impossible that she'd find me attractive, that it'd be creepy or pathetic of me to try to date her, etc.

No and no.

I'm in danger of putting way too much pressure on any given opportunity--and of unloading a decade of insecurities on this unsuspecting woman

Don't worry about that right now. Worry about it after you email her if you want. Great topic to talk about in therapy.

So maybe she thought she'd misread things, too? Or she's almost as bad at this dating thing as I am?

When I was 19, and first starting to date my first serious boyfriend, we had ZERO physical contact, not even a hug or handshake, for our first few dates and I was convinced he wasn't attracted to me and/or gay and just kept going out with me because he enjoyed my company. It took sitting on his couch next to each other, alone, listening to music for several hours, bumping hands a bunch of times, then awkwardly holding hands for a while, before I worked up the nerve to try kissing him. So, definitely maybe, and definitely maybe.

But wasn't my failure to stick the landing on these dates (or non-dates?) a big red flag, showing her I'm all inept and sexually/romantically immature?

NO, just banish this thought, okay? Don't shoot your own self in the foot by assuming others think the worst of you out of all the possible things they can think, which you have no way to know.

--or convincing her that I'm not interested?


Do I need to make clear why I wasn't all suave and self-assured?

NO!!!!!! Definitely don't do that. Just don't bring it up.

I suggest you email her and say something like,

"Hey, I had a really great time with you these past few days. I'd love to take you out on a date when I get back to Home State, if you'd be up for that! Either way, thanks for the wonderful company and I hope we can spend more time together when I get back. -- Your Name"
posted by cairdeas at 7:43 PM on August 26, 2013 [40 favorites]

Exactly what cairdeas said.
posted by eviemath at 7:45 PM on August 26, 2013

In addition to what Cairdeas advised... Over the next few weeks while you're still in Faraway Land, text/email her cell phone pics of evocative street scenes, places pertinent to your time together, stuff that relates to her work, etc. Show that you listened to her and valued your time together while keeping it light.
posted by carmicha at 7:49 PM on August 26, 2013




Then hold her hand and maybe kiss her at an appropriate time.

It'll feel scary, but that's a good thing. All the best stuff is a little scary.

The voices in your head are scared of change, and your job is to embrace change in spite of them.
posted by Sebmojo at 7:50 PM on August 26, 2013 [12 favorites]

I was going to suggest almost exactly what cairdeas suggested in their last paragraph. A message that 1) says you had a great time and would like to see her some more and 2) uses the word "date" in some context involving the two of you possibly doing something in the future. Those are the two essential things.
posted by hattifattener at 7:57 PM on August 26, 2013 [2 favorites]

Tell her that you really regret not kissing her the other night.
posted by gentian at 8:02 PM on August 26, 2013 [1 favorite]

I've looked askance at plenty of relationship age differences, and I don't think the one you describe is a big deal at all.

I would definitely go with the "invite her to a date at a specific time" type of message. I think you have a good shot since she obviously enjoyed spending time with you. Good luck!
posted by mlle valentine at 8:10 PM on August 26, 2013

Sorry if this answer isn't specific enough but don't worry that things were a little awkward at first - it's not uncommon! I think you can acknowledge this in a way that's charming and not rife with insecurity. I find it sweet when guys are a little nervous or shy to talk to me, it makes me feel special. However signs of insecurity about themselves is a huge turn off and this line can be hard to walk. Stay away from words like "awkward" or "scared" or even "sorry" in your email - you have nothing to apologize for. And never ever hint that the reason that you didn't go for it was because you assumed that she would reject you - that will surely place the thought in her head. Tell her something like you were waiting for the perfect moment to ask her out but you got butterflies and missed your chance and you're gonna make it up to her when you're back in the states. Then suggest specific plans for a date. Acknowledge that she made you a little dizzy and shy in a way that's flattering to her and not degrading to you and then follow up with directly and assertively asking her out.

Also, if it makes you feel better on the first date I went on with my current boyfriend things were awkward at the end so I decided to just kiss him. He barely reciprocated, acted like he was appalled, and then trotted off. I thought I would never see him again. We laugh about it now. If it doesn't work out it's not because you weren't suave enough - if you're on the same page you'll laugh at all those moments later.
posted by Valkyrie21 at 8:17 PM on August 26, 2013 [1 favorite]

I would let it float. Dudes have little mystery, so don't worry if a period of doing your own thing adds a bit of fog to the situation.
posted by Ironmouth at 8:19 PM on August 26, 2013

Email only with your very sincere and true interest in "having a night out in [HOMETOWN] as you did in [FARAWAY LAND]" as soon as you get back. Be patient, and keep communications ongoing as a month is a long time, and you won't know how her situation may have changed otherwise. Don't deliver any romantic bombshells or overtures via email because you are still getting to know her, and it may seem a bit sudden. Especially if she's got an awkwardness to her as well, you'll want to be in person before making any grand statements, to get a better read on her response.
posted by Cold Lurkey at 8:47 PM on August 26, 2013

i think email is a good medium. if she rejects you it will be easier for both of you, and when you are both in the same city it will be less awkward.

you should tell her you want to date her, and just mention briefly that this is why you might have seemed a little weird when you two were hanging out.

when she rejects you you can reply with something like "ok, that's cool. i'm not 100% sure if i can deal with just being friends, but i'll think about it, and when you get back i'll let you know."
posted by cupcake1337 at 9:15 PM on August 26, 2013

My read here is that you're both interested but both dating challenged. I think this mainly because she was willing to spend most of two days in a row with you. Other explanations are possible.

You should certainly keep up contact, but not in a desperate or pestery way. As a rule of thumb, take turns interacting. Don't message her a bunch of times in a row. Wait for her to reply instead.

It's OK to discuss your feelings in email, but I'd suggest trading a few emails first and seeing what the temperature of the conversation is. It's OK to wait until you're in person also.

Don't talk about how lame you are, how old you are, how little you've dated, or any other reassurance-seeking ploys. If you want to talk about feelings, show a little courage and just tell her you're into her. "I mean I LIKE like you" would be fine, or assorted other suggestions above.

It's OK if you get rejected. Really. If you have gone 10 years without dating, and you try and fail here, once the sting wears off I think you'll feel pretty good about having made the attempt.

If you end up hanging out again, don't wait until the end of the date to try to kiss her. Try to hold her hand, or even just touch her hand in a deliberate way, earlier in the date.
posted by mattu at 9:18 PM on August 26, 2013 [1 favorite]

Tell her something like ... you got butterflies ... she made you a little dizzy and shy

If I were into you, and you seemed sweet and genuine, I would be super super charmed by this. Definitely way better than putting it as "awkward" and "scared." [I still think you should avoid any talk of this initially though, unless she asks, or after you two have already made an explicit romantic connection.]
posted by cairdeas at 9:32 PM on August 26, 2013 [1 favorite]

30 and 25 is nothing. It's not remotely like 25 and 20. And it gets to be less and less meaningful as you get older.
posted by empath at 9:57 PM on August 26, 2013 [3 favorites]

Also, another thing about how you're almost 30 while she's 25 and you worry she wouldn't find you attractive... I am close to your age (but female) and I have started feeling like it's the age where EVERYONE is attracted to you. Like for most of my life I have gotten serious attention from some people close to my age and then quite a bit of gross skeezy attention from much older men. I feel like, for the past year, I have been getting real, serious attention from guys in their teens, 20s, 30s, and 40s and respectful light flirting from guys in their 50s and even 60s.

This is something that I never expected, as a woman, because the big message from society is, "Once you're over 25 you're an old hag who nobody but men twice your age will ever look at againnnnnn!!!! You will be bitterly jealous of younger women for everything from their skin the fashion styles they "can" wear to their dating lives!!!"

It's actually like the opposite! I am not jealous of people in those years in the least, because I feel like I have so much more to offer now compared to when I was that age. I actually feel like there is no difference between say, my 24 year old self, and my current self, except that almost everything about me ranges from better to WAY WAY better.

And the different treatment from guys is like wow. Before, I felt like most guys who approached me were like, here's someone I might want to sleep with. Now I feel like most guys who approach me are like, "this might be my future wife and mother of my children." I have no idea what's going on with the teens and college-aged ones because I'm getting more attention from them now than ANY point in my life, including when I was a teen and in college, but maybe they're thinking of all the "older woman" tropes.

That's my experience as a woman. I think it should be much more the case for you as a guy, that women in their mid-20s who are interested in something serious would be very very interested in a guy in his late 20s or early 30s, maybe more so than any other age group.
posted by cairdeas at 10:16 PM on August 26, 2013 [7 favorites]

My two cents: I'm awkward and have wrestled with wanting to kiss or touch someone but not being able to force myself to actually do it many times. Several of those times I've sent an email the next day saying something along the lines of "Hey, I really like you but I'm awkward and it's hard for me to express my feelings in person for the first time"

I'm not going to lie and tell you this has always resulted in me getting the girl, but I have never regretted doing it.
posted by neilb449 at 12:06 AM on August 27, 2013

we had these awkward pauses when my insecurities and my desire to--give a goodnight kiss? Express my attraction? Or something--were warring.

Look, you don't have to be profound and you don't have to try to come up with the thing to say/do that will perfectionize the relationship such that you elope next weekend. Take it slow, say something like, "this is fun." You don't know what to do because you don't have enough information yet. Practice the information part, not the jumping to conclusions part.
posted by rhizome at 2:15 AM on August 27, 2013 [3 favorites]

Also, I'm almost 30 while she's almost 25. This age difference, among other things, had (has) my internal voices of doubt yammering away in overdrive that it would be impossible that she'd find me attractive, that it'd be creepy or pathetic of me to try to date her, etc.

There is an adage that the older partner should not date anybody younger than half their age plus seven. Here you can see that shown graphically to give both lower an upper age bounds - at 30 this gives you a green light for women between 22 and 53. For her the range is about 20 through to 43. The algorithm a bit arbitrary but it does seem to make good practical sense. Rest assured that the two of you dating are not going to cause tongues to wag, curtains to twitch and police to pay visits - you are not even near the extremes.
posted by rongorongo at 3:46 AM on August 27, 2013

Don't worry about the age difference. That's not a huge gap at all and in a few years a 5-year difference is going to seem as negligible as a 5-month difference. I speak from experience.

As a woman who has dated too many arrogant, narcissistic, overconfident jerks, a guy who is genuine but shy and awkward is a breath of fresh air. It is extremely charming when a guy is nervous but expresses interest. I would say that spending all of that time together seems like an expression of interest on both sides.

Most women understand that when a guy seeks them out, he's interested. I personally have never had a guy say "let me take you out on a date" or anything. To me, that sounds kind of awkwardly formal and old-fashioned. I think it's fine to email back and forth for a while, especially with light bantering. Send her a link to something that made you think of her, for example. As the time for you to get home draws closer, mention how you hope to see her again soon. Then make a plan to have coffee or something.

Also, people seem to want to rush relationships. There is actually a way to delay physical affection while at the same time avoiding the Friend Zone. This is a great approach to relationships in general because it builds trust and emotional intimacy and preserves that feeling of chemistry and attraction. Here's how:

- Make prolonged eye contact and smile a lot while talking.
- Use open, friendly, interested body language. Here is a start. You should Google the topic. We are hardwired as humans to subconsciously read signs of attraction; if we weren't, our species would not have survived. (Sometimes shy guys inadvertently use closed body language even if they're interested, which can confuse women, so you may need to cultivate it consciously).
- Ask questions that show you're interested without prying.
- Tease her a little bit, but not about anything mean.
- Talk about your ideas of what constitutes a healthy relationship.
- Be encouraging to her ideas and goals. (For example, you can say something like, "I can see you being a really engaging professor," or something like that. Just make sure you actually believe it).
- Share your emotions. You don't have to let it all hang out, just something you'd share with a friend. That builds connection.
- If you're out together and you run into someone, introduce her by name, NOT "this is my friend Jennifer." When guys use that "my friend" line it can come across as a message to the girl that he only likes her platonically or as a potential FWB.
- Hug goodbye, but don't make it prolonged.

Try to think of it as a dance. Personally, I like it when guys "lead." A lot of other women feel the same, though not all. For me, it's reassuring when a guy sets the pace of the relationship and initiates contact often, because then I know he's interested. It also shows he's reliable and trustworthy. Also, if he's holding back on getting physical I know he's interested in more than just my body.

I also recommend seeking the advice of guys who are a bit older than you, and in serious relationships or married, about how they built their relationships. If you have older brothers or friends whose relationships you envy, they'd be good mentors.

If you want a woman's perspective along the way, feel free to MeMail me.
posted by Rainflower at 5:11 AM on August 27, 2013 [2 favorites]

Do send her an email using Cairdeas's wording. It's really perfect. When she responds positively, you can keep sending each other short emails. Just little blurbs telling her about what you're doing. Ask her what she's doing, etc.

When you get back home, ask her out on a date. When she accepts that's your signal that she's open to being kissed. I like the Woody Allen-Annie Hall method.

Seriously, it will be perfect.

Once you make it clear that you like-like her, trust me, you'll have to beat her off with a stick.

Remember, she's insecure too.
posted by Ruthless Bunny at 7:13 AM on August 27, 2013 [1 favorite]

Aw, the first time me and my boyfriend kissed we were watching movies at his house. As a grown, adult woman who has been on many dates, I thought it was obvious that I would not have accepted a date at a man's house if I did not feel comfortable with said man kissing me. Clearly it was not because we watched TWO WHOLE MOVIES as we inched slowly and awkwardly closer to each other on the couch. I remember thinking as we were sitting almost on top of each other, "Why hasn't he put his arm around me? What more do I have to DO?!?!?!?!" Meanwhile he was sitting there thinking, "Does she really want to be sitting this close to me, or is the couch cushion forcing it? Should I put my arm around her? I don't want her to think I don't respect her boundaries."

My point is, it was INCREDIBLY CUTE. So if she likes you already, she won't have felt it was awkward. Contact her and ask her out!
posted by chainsofreedom at 9:15 AM on August 27, 2013 [5 favorites]

Age differences? Bah.

One of the great loves I have ever had the pleasure to witness up-close was between two professional musicians. Almost 20 years between them and they were crazy for each other every minute of every day.

Five years is nothing.
posted by trinity8-director at 2:06 PM on August 27, 2013

So I am the anonymous asker, now safely ensconced in a sock puppet, just dropping in to say that I did ask her on a date (more or less cairdeas's script, although I said "go on a date" instead "of take you on a date"), she did say yes, we have since been reunited and had many dates since then, etc etc. Thanks folks, I might not have mustered the courage without you!
posted by sauberbrezel at 12:15 AM on October 18, 2013 [7 favorites]

posted by cairdeas at 3:04 PM on October 18, 2013 [1 favorite]

« Older Etiquette for correspondence with a professor...   |   Subflooring subflooring... Newer »
This thread is closed to new comments.